Quantum dot-containing material and method of making same, crosslinked material and method of making same, and light emitting device

Abstract

This invention provides a quantum dot-containing material, a method for preparing a quantum dot-containing material, a cross-linked material containing quantum dots and its preparation method, and a light-emitting device comprising a quantum dot-containing material. The quantum dot-containing material may include quantum dots and organic groups chemically bonded to the surface of the quantum dots. The organic groups may include azide groups and charge-transporting groups, and the charge-transporting groups may not be unsubstituted phenyl groups.

Description

[0001] Cross-references to related applications

[0002] This application is based on and claims priority to Korean Patent Application No. 10-2020-0182419, filed with the Korean Intellectual Property Office on December 23, 2020, and all benefits derived therefrom, the entire contents of which are incorporated herein by reference. Technical Field

[0003] This disclosure relates to materials, and more specifically to materials containing quantum dots, methods for preparing materials containing quantum dots, crosslinked materials containing quantum dots, and light-emitting devices including materials containing quantum dots. Background Technology

[0004] Among light-emitting devices, organic light-emitting devices (OLEDs) are self-emissive devices. Compared with devices of related technologies, they have wide viewing angles, high contrast, short response times, and excellent characteristics in terms of brightness, driving voltage, and response speed. Furthermore, they produce full-color images.

[0005] An OLED may include a first electrode on a substrate, and a hole transport region, an emitter layer, an electron transport region, and a second electrode sequentially stacked on the first electrode. Holes supplied from the first electrode can move towards the emitter layer through the hole transport region, and electrons supplied from the second electrode can move towards the emitter layer through the electron transport region. Charge carriers, such as holes and electrons, recombine in the emitter layer to generate excitons. Excitons can transition from an excited state to a ground state, thus producing light.

[0006] Various types of organic light-emitting devices are known. However, there is still a need for OLEDs with improved hole transport capabilities, long lifetimes, or both. Summary of the Invention

[0007] One or more embodiments include a quantum dot-containing material, a method for preparing a quantum dot-containing material, a crosslinked material containing quantum dots, a method for preparing a crosslinked material, and a light-emitting device including a crosslinked material, wherein the quantum dot-containing material can be surface-modified with organic groups including thermal and photocrosslinking groups to provide a crosslinked material with excellent or improved hole transport capability and long lifetime.

[0008] Additional aspects 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 practicing the embodiments presented in this disclosure.

[0009] According to the embodiments, the materials containing quantum dots may include:

[0010] Quantum dots; and

[0011] Organic groups chemically bonded to the surface of quantum dots

[0012] The organic groups may include azide groups and charge transport groups, and

[0013] The charge-transfer group may not be an unsubstituted phenyl group.

[0014] According to the embodiments, a method for preparing materials containing quantum dots may include:

[0015] The quantum dots undergo a chemical reaction with the precursors of organic groups, thereby chemically bonding the surface of the quantum dots to the organic groups.

[0016] According to an embodiment, a cross-linked material containing quantum dots can be provided.

[0017] According to the embodiments, the method for preparing crosslinked materials may include:

[0018] A quantum dot-containing material and solvent according to any of the above embodiments are provided on a substrate; and

[0019] To crosslink materials containing quantum dots.

[0020] According to an embodiment, the light-emitting device may include:

[0021] First electrode,

[0022] The second electrode facing the first electrode, and

[0023] An intermediate layer between the first and second electrodes, including the emission layer.

[0024] The light-emitting device may include cross-linked materials as described herein. Attached Figure Description

[0025] From the following description taken in conjunction with the accompanying drawings, the above and other aspects, features, and advantages of certain embodiments of the present invention will become more apparent, in which the drawings are shown.

[0026] Figure 1 This is a schematic cross-sectional view of a quantum dot-containing material according to an embodiment;

[0027] Figure 2 This is a schematic cross-sectional view of the cross-linked material according to the embodiment;

[0028] Figure 3 This is a schematic cross-sectional view of the light-emitting device according to an embodiment;

[0029] Figure 4 A schematic cross-sectional view of a light-emitting device according to an embodiment; and

[0030] Figure 5 This is a schematic cross-sectional view of a light-emitting device according to an embodiment. Detailed Implementation

[0031] Reference will now be made in detail to embodiments, examples of which are shown in the accompanying drawings, wherein similar reference numerals always refer to similar elements. In this respect, embodiments of the invention may take different forms and should not be construed as limited to the description set forth herein. Therefore, embodiments are described below only with reference to the accompanying drawings to explain various aspects of this description. As used herein, the term “and / or” includes any and all combinations of one or more of the associated listed items. Throughout the disclosure, the expression “at least one of a, b, and c” indicates only a, only b, only c, both a and b, both a and c, both b and c, all a, b, and c, or variations thereof.

[0032] What will be understood is that when an element is said to be "on top of" another element, it can be in direct contact with the other element, or there can be an intermediary element between them. Conversely, when an element is said to be "directly" "on" another element, there is no intermediary element.

[0033] It will be understood that although the terms first, second, third, etc., may be used herein to describe various elements, components, areas, layers, and / or portions, these elements, components, areas, layers, and / or portions should not be limited by these terms. These terms are only used to distinguish one element, component, area, layer, or portion from another element, component, area, layer, or portion. Therefore, without departing from the teachings of this embodiment, the first element, component, area, layer, or portion discussed below can be referred to as the second element, component, area, layer, or portion.

[0034] The technical terms used herein are for the purpose of describing particular implementations only and are not intended to be limiting. As used herein, the singular forms “a,” “an,” and “the” are also intended to include the plural forms unless the context clearly indicates otherwise.

[0035] The word “or” means “and / or”. It will be further understood that, when used in this specification, the terms “comprises,” “comprising,” “includes,” and / or “including” indicate the presence of the stated features, areas, integers, steps, operations, elements, and / or components, but do not preclude the presence or addition of one or more other features, areas, integers, steps, operations, elements, components, and / or groups thereof.

[0036] Unless otherwise defined, all terms used herein (including technical and scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art to which the general concept of this invention pertains. It will be further understood that terms, such as those defined in common dictionaries, should be interpreted as having meanings consistent with their meanings in the relevant field and in the context of this disclosure, and will not be interpreted in an idealized or overly formal sense unless expressly defined herein.

[0037] Exemplary embodiments are described herein with reference to cross-sectional views as schematic illustrations of idealized embodiments. Thus, variations in the shapes illustrated are expected due to factors such as manufacturing techniques and / or tolerances. Therefore, the embodiments described herein should not be construed as limited to the specific shapes of the regions shown herein, but will include deviations in shape, for example, due to manufacturing processes. For instance, regions shown or described as flat may generally have rough and / or non-linear characteristics. Furthermore, sharp corners in the illustrations may be rounded. Therefore, the regions shown in the figures are schematic in nature, and their shapes are not intended to show precise shapes of the regions and are not intended to limit the scope of the claims.

[0038] Given the measurements discussed and the errors associated with the measurement of a particular quantity (i.e., limitations of the measurement system), the terms “about” or “approximately” as used herein include the stated value and mean within an acceptable deviation for that particular value as determined by one of ordinary skill in the art. For example, “about” can mean within one or more standard deviations, or within ±20%, ±10%, ±5% of the stated value.

[0039] The term "room temperature" as used in this article refers to a temperature of approximately 25°C.

[0040] In any expression, *, *', and *” each indicate a binding site with an adjacent atom or adjacent functional group.

[0041] Figure 1 Description

[0042] Figure 1 The quantum dot-containing material 131 shown may include quantum dots 131A and organic groups 131B chemically bonded to the surface of the quantum dots. The quantum dot-containing material 131 may include at least one of the organic groups 131B. The organic group 131B may include an azide group and a charge transport group, and the charge transport group may not be an unsubstituted phenyl group.

[0043] In the following text, we will combine Figure 1 The invention describes a quantum dot-containing material 131 according to an embodiment and a method for preparing the quantum dot-containing material 131 according to an embodiment.

[0044] Quantum dot 131A in material 131 containing quantum dots

[0045] exist Figure 1 The quantum dot-containing material 131 may include quantum dot 131A.

[0046] In implementations, quantum dots may include: group II-VI semiconductor compounds; group III-V semiconductor compounds; group III-VI semiconductor compounds; group I-III-VI semiconductor compounds; group IV-VI semiconductor compounds; group IV elements or compounds; or any combination thereof.

[0047] In implementation, the quantum dot may be a group II-VI semiconductor compound; a group III-V semiconductor compound; or any combination thereof.

[0048] In this embodiment, the quantum dots may include: CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, or MgS;

[0049] CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe or MgZnS;

[0050] CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe or HgZnSTe;

[0051] GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs or InSb;

[0052] GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, InPSb or GaAlNP;

[0053] GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs or InAlPSb;

[0054] InZnP, InGaZnP, or InAlZnP; or any combination thereof.

[0055] In implementation, the quantum dot may have a monolayer structure in which the concentration of each element contained in the quantum dot is uniform, or the quantum dot may be comprised as a core-shell bilayer structure.

[0056] In one embodiment, the interface between the core and the shell may have a concentration gradient, wherein the concentration of elements present in the shell decreases toward the core. In another embodiment, the quantum dot may be a core-shell bilayer structure.

[0057] In an embodiment, the material included in the shell may be a group II-VI semiconductor compound, and / or the material included in the core may be a group III-V semiconductor compound.

[0058] In embodiments, the material included in the shell may include: CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, or MgS;

[0059] CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe or MgZnS;

[0060] CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, or HgZnSTe; or any combination thereof.

[0061] In an embodiment, the material included in the core may include: GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, or InSb;

[0062] GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, InPSb or GaAlNP;

[0063] GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs or InAlPSb;

[0064] InZnP, InGaZnP, or InAlZnP; or any combination thereof.

[0065] Quantum dot 131A can be understood by referring to the description of quantum dots provided in this article.

[0066] Organic groups 131B in quantum dot material 131

[0067] exist Figure 1 The quantum dot-containing material 131 may include an organic group 131B. The organic group may include an azide group and a charge transport group, and the charge transport group may not be an unsubstituted phenyl group.

[0068] In the embodiments, the charge-transporting group in the organic group can be an electron-donating group or an electron-withdrawing group.

[0069] In the implementation method, in the charge transport group,

[0070] Electron-donating groups can be unsubstituted or substituted with at least one R group. 20a Substituted π-electron-rich C3-C 60 Cyclic groups, or -N(Ar2)(Ar3),

[0071] Ar2 and Ar3 can each be independently unsubstituted or replaced by at least one R. 20a Substituted π-electron-rich C3-C 60 Cyclic groups,

[0072] Electron-withdrawing groups can be:

[0073] -F, -CFH2, -CF2H, -CF3, -CN, or -NO2;

[0074] C1-C substituted by at least one of -F, -CFH2, -CF2H, -CF3, -CN or -NO2 60 Alkyl; or

[0075] Not replaced or replaced by at least one R 10a Substituted nitrogen-containing C1-C lacking π electrons 60 Cyclic groups,

[0076] R 10a Possible forms:

[0077] Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl, cyano, or nitro;

[0078] C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 alkynyl group, C1-C 60 alkylthio or C1-C 60 Alkoxy groups, which are individually unsubstituted or substituted with the following groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, -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 -P(=O)(Q) 11 (Q) 12 ), or any combination thereof;

[0079] C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryloxy or C1-C 60 Heteroaryl thiols, each independently unsubstituted or substituted with the following groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, -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 -P(=O)(Q) 21 (Q) 22 ), or any combination thereof; or

[0080] -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 ) or -P(=O)(Q 31 (Q) 32 ),

[0081] Among them, Q 11 To Q 13 Q 21 To Q 23 And Q 31 To Q 33 Each can be independently represented as: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkoxy group; C1-C 60 Alkylthio group; or, C3-C 60 Carbocyclic groups or C1-C 60 Heterocyclic groups, which are independently unsubstituted or substituted with the following groups: deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 Alkoxy, C1-C 60 Alkylthio, phenyl, biphenyl, or any combination thereof, and

[0082] R 20a Possible forms:

[0083] Deuterium (-D), hydroxyl or nitro;

[0084] C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C60 alkynyl group, C1-C 60 Alkyl thio or C1-C 60 Alkoxy groups, each independently unsubstituted or substituted with the following groups: deuterium, hydroxyl, nitro, C3-C rich in π electrons. 60 Cyclic groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, -Si(Q) 41 (Q) 42 (Q) 43 -N(Q) 41 (Q) 42 -B(Q) 41 (Q) 42 ), or any combination thereof;

[0085] C3-C rich in π electrons 60 Cyclic groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryloxy or C1-C 60 Heteroaryl thiols, each independently unsubstituted or substituted with the following groups: deuterium, hydroxyl, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C1-C 60 Alkyl thiols, C3-C rich in π electrons 60 Cyclic groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryloxy or C1-C 60 heteroaryl thiols, -Si(Q) 51 (Q) 52 (Q) 53 -N(Q) 51 (Q) 52 -B(Q) 51 (Q) 52 ), or any combination thereof; or

[0086] -Si(Q 61 (Q) 62 (Q) 63 -N(Q) 61 (Q) 62 ) or -B(Q 61 (Q) 62 ),

[0087] Among them, Q 41 To Q 43 Q 51 To Q 53 And Q 61 To Q 63 Each of the following is independently: hydrogen; deuterium; hydroxyl group; nitro group; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkoxy group; C1-C 60 Alkylthio group; or an unsubstituted or π-electron-rich C3-C group substituted with the following groups. 60 Cyclic groups: deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 Alkoxy, C1-C 60 Alkylthio, phenyl, biphenyl, or any combination thereof.

[0088] For example, the electron-donating group in a charge-transporting group can be...

[0089] Phenyl, heptalenyl, indene, naphthyl, azuleyl, indaryl, acenaphthenic, fluorenyl, spiro-bisfluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthreneyl, phenanthreneyl, anthraceneyl, fluoranthraceneyl, triphenyleneyl, pyrene, Naphtho-naphthyl, furanyl, perylene, pentaphenyl, hexaphenyl, pentapheneyl, rubiceneyl, hexabenzophenyl, ovophenyl, pyrroleyl, furanyl, thiopheneyl, isoindoleyl, indoleyl, indoleyl, benzofuranyl, benzothiopheneyl, benzosilylopadienyl, naphthopyrroleyl, naphthofuranyl, naphthothiopheneyl, naphthosilylopadienyl, benzocarbazoyl, dibenzocarbazoyl, dibenzofuranyl, dibenzothiopheneyl Fenyl, carbazolyl, dibenzosilicyclopentadienyl, indobenzocarbazolyl, indolocarbazolyl, benzofuranocarbazolyl, benzothiophenecarbazolyl, benzosilicyclopentadienocarbazolyl, triindolophenyl, pyrrolopheneyl, furanopheneyl, thiopheneyl, benzonaphthiofuranyl, benzonaphthiopheneyl, (indolo)pheneyl, (benzofurano)pheneyl, (benzothiophene)pheneyl or -N(Ar2)(Ar3), each independently unsubstituted or substituted with at least one R 20a It can be replaced, but the implementation method is not limited to this.

[0090] Ar2, Ar3 and R 20a You can refer to the Ar2, Ar3 and R provided in this article respectively. 20a To understand this, we need to refer to the description.

[0091] For example, electron-withdrawing groups in charge transport groups can be

[0092] Imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, indazolyl, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, phthalazinyl, naphridinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, cenolinyl, phenanthridine, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzooxazolyl, isobenzoisooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, azadibenzosilazopyranyl, or pyridinopyrazinyl, each independently unsubstituted or substituted by at least one R 10a replace.

[0093] R 10a You can refer to the R provided in this article 10a To understand this, we need to refer to the description.

[0094] For example, charge transport groups can be

[0095] Not replaced or replaced by at least one R 20a The carbazolium group is substituted, but the implementation methods are not limited to this.

[0096] In the implementation method, the organic group may be

[0097] Groups represented by Formula 1:

[0098] Formula 1

[0099] *-X1-Z1-(A1) m -Z2-(A2) n -Z3-T1 1

[0101] Wherein, A1 and A2 are each independently a group represented by formula 2-1 or formula 2-2.

[0102]

[0103] In Equation 1,

[0104] X1 can be O or S.

[0105] In the implementation, X1 can be S.

[0106] Z1 to Z3 can each be independently:

[0107] single bond;

[0108] *-N(R 1a)-*', *-O-*', *-S-*' or *-C(=O)-*'; or

[0109] C1-C 60 Alkylene, C1-C 60 Oxyalkylene, C6-C 60 aryl or C6-C 60 Oxyaryl groups, each independently unsubstituted or substituted with the following groups: deuterium, hydroxyl, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, phenyl, biphenyl, or any combination thereof.

[0110] T1 can be an end base.

[0111] As used herein, the term "terminal group" refers to a constituent unit bonded to the end of a polymer, and various terminal groups can be selected according to the synthetic methods of the organic group precursors described herein. Those skilled in the art will understand that various changes in form and detail are possible.

[0112] For example, the terminal group can be hydrogen, deuterium, cyano, nitro, unsubstituted, or with at least one R group. 10a Replacement C1-C 60 Alkyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl thio group, unsubstituted or with at least one R 10a Replacement C3-C 60 Carbocyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, unsubstituted or with at least one R 10a Replacement C6-C 60 aryloxy group, unsubstituted or with at least one R 10a Replacement C6-C 60 Aryl thiols, unsubstituted or with at least one R 10a Replacement C1-C 60 Heteroaryl groups, unsubstituted or with at least one R 10a Replacement C1-C 60Heteroaryl thiols, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2).

[0113] R 10a You can refer to the R provided in this article 10a To understand this, we need to refer to the description.

[0114] A1 and A2 can each be independently a group represented by formula 2-1 or formula 2-2.

[0115] At least one of the m A1 and n A2 can be a group represented by Equation 2-1.

[0116] m and n can each be an integer from 50 to 1,000 independently.

[0117] In the implementation, in Equation 1, m and n can each be an integer from 50 to 500 independently.

[0118] *Indicates the binding sites on the surface of the quantum dot.

[0119] In equations 2-1 and 2-2,

[0120] Y1 and Y2 can each be independent single bonds, or unsubstituted or bonded by at least one R. 10a Replacement C1-C 10 Alkylene.

[0121] L1 and L2 can each be independently a single bond, unsubstituted, or bonded by at least one R. 10a Replacement C3-C 60 The carbocyclic group, or the unsubstituted group or the group with at least one R 10a Replacement C1-C 60 Heterocyclic groups.

[0122] a1 and a2 can each be an integer from 1 to 3 independently.

[0123] Ar1 can be either unsubstituted or replaced by at least one R. 20a Substituted electron-donating groups, or unsubstituted or substituted with at least one R 10a Substituted electron-withdrawing groups, and

[0124] When L1 is a single bond, Ar1 may not be an unsubstituted phenyl group.

[0125] R1 and R2 can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 10 Alkyl, C2-C 10 Alkenyl, C2-C 10alkynyl group, C1-C 10 Alkyl thio or C1-C 10 Alkyl group.

[0126] *' and *” each indicate the binding site with the adjacent atom.

[0127] R 10a and R 20a You can refer to the R provided in this article respectively. 10a and R 20a To understand this, use the description. R 1a You can refer to the R provided in this article 10a To understand this, we need to refer to the description.

[0128] In the implementation, Equation 2-2 of A1 and A2 in Equation 1 can be represented by Equation 2-2a or Equation 2-2b:

[0129]

[0130] Among them, in equations 2-2a and 2-2b,

[0131] Y2, R2, L2, and a2 can be understood by referring to the descriptions of Y2, R2, L2, and a2 provided in this article.

[0132] R 31 To R 33 Each can refer to the R provided in this article. 20a To understand from the description,

[0133] c34 can be an integer from 0 to 4.

[0134] c35 can be an integer from 0 to 5.

[0135] c38 can be an integer from 0 to 8.

[0136] Among them, substituent R 31 Existing in having R 31 The substituent bonds pass through each ring, and

[0137] *' and *” each indicate the binding site with the adjacent atom.

[0138] In embodiments, the molar ratio of azide groups to charge-transporting groups in the organic group can be in the range of about 1:1 to about 1:10, for example, about 1:1 to about 1:9, about 1:1 to about 1:8, about 1:1 to about 1:7, about 1:1 to about 1:6, about 1:1 to about 1:5, about 1:1 to about 1:4, about 1:1 to about 1:3, or about 1:1 to about 1:2.

[0139] In embodiments, in materials containing quantum dots, the molar ratio of organic groups to quantum dots can be in the range of about 1:100 to about 1:1,000. For example, in materials containing quantum dots, the molar ratio of organic groups to quantum dots can be in the range of about 1:100 to about 1:900, about 1:100 to about 1:800, about 1:100 to about 1:700, about 1:100 to about 1:600, about 1:100 to about 1:500, about 1:100 to about 1:400, about 1:100 to about 1:300, or about 1:100 to about 1:200.

[0140] In embodiments, the average diameter (D50) of the quantum dot-containing material can be in the range of about 40 nanometers (nm) to about 1000 nm. For example, the average diameter of the quantum dot-containing material can be in the range of about 50 nm to about 900 nm, about 60 nm to about 800 nm, about 70 nm to about 700 nm, about 80 nm to about 600 nm, about 90 nm to about 500 nm, about 100 nm to about 400 nm, about 100 nm to about 300 nm, or about 100 nm to about 200 nm.

[0141] Method for preparing materials containing quantum dots 131

[0142] Methods for preparing materials 131 containing quantum dots may include:

[0143] A chemical reaction is made between quantum dot 131A and the precursor of organic group 131B, so that the surface of the quantum dot is chemically bonded to the organic group.

[0144] In the embodiments, the precursor of organic group 131B can be represented by formula 1(1):

[0145] Equation 1(1)

[0146] H-X1-Z1-(A1) m -Z2-(A2) n -Z3-T1 1(1)

[0148] Wherein, A1 and A2 are each independently a group represented by formula 2-1 or formula 2-2.

[0149]

[0150] The terms X1, Z1 to Z3, T1, A1, A2, m and n in Equation 1(1) and Y1, Y2, L1, L2, a1, a2, Ar1, R1, R2, *' and *” in Equations 2-1 and 2-2 can be understood by referring to the descriptions of X1, Z1 to Z3, T1, A1, A2, m and n and Y1, Y2, L1, L2, a1, a2, Ar1, R1, R2, *' and *” provided in this document.

[0151] In an embodiment, when the precursor of quantum dot 131A reacts with the organic group 131B to chemically bond the surface of the quantum dot to the organic group, the chemical reaction may include the formation of covalent bonds between the surface of the quantum dot and the organic group.

[0152] Figure 2 Description

[0153] Figure 1 The quantum dot-containing material 131 can be cross-linked to form Figure 2 The cross-linking material 132 in it. Figure 2 The crosslinking material 132 may include residue 132C, which is derived from the crosslinking reaction between the azide group in the organic group 131B of the quantum dot-containing material 131 and the adjacent organic group. The azide group and the adjacent organic group may be included in i) the same quantum dot-containing material 132C(i) or ii) each may be included in a different quantum dot-containing material 132C(ii).

[0154] In the following text, we will combine Figure 2 The crosslinking material 132 according to the embodiments and the method for preparing the crosslinking material 132 according to the embodiments are described.

[0155] Crosslinking material 132

[0156] Figure 2 A crosslinking material 132 according to an embodiment is shown. The crosslinking material 132 may be a crosslinked material (i.e., a product) of the material 131 containing quantum dots.

[0157] In this embodiment, the residues originate from the cross-linking reaction between the azide group in the organic groups of the quantum dot material and the adjacent organic groups.

[0158] In an embodiment, the crosslinking material 132 may include residue 132C, which originates from the crosslinking reaction between the azide group in the organic group 131A of the quantum dot-containing material 131 and the adjacent organic group. The azide group and the adjacent organic group may be included in i) the same quantum dot-containing material 132C(i) or ii) each may be included in a different quantum dot-containing material 132C(ii).

[0159] In an embodiment, residue 132C in the crosslinked material 132 may include

[0160] Groups represented by Formula 4:

[0161] Formula 4

[0162]

[0163] Among them, *', *” and *”' each indicate the binding site with the adjacent atom.

[0164] According to an embodiment, the crosslinked material may be in the form of a film. The thickness of the film may be in the range of about 0.1 micrometers (μm) to about 700 μm. For example, the thickness of the film may be in the range of about 0.1 μm to about 600 μm, about 0.1 μm to about 500 μm, about 0.1 μm to about 400 μm, about 0.1 μm to about 300 μm, about 0.1 μm to about 200 μm, about 0.1 μm to about 100 μm, or about 0.1 μm to about 50 μm.

[0165] Method for preparing crosslinked material 132

[0166] The method for preparing crosslinked material 132 may include providing a quantum dot-containing material 131 and a solvent on a substrate; and

[0167] Crosslinking of material 131 containing quantum dots.

[0168] In an embodiment, the solvent used when providing the quantum dot-containing material 131 can be any suitable solvent capable of dissolving the quantum dot-containing material.

[0169] For example, the solvent in the quantum dot-containing material 131 may be: alkylene glycol alkyl ethers, such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, or propylene glycol monoethyl ether; diethylene glycol dialkyl ethers, such as diethylene glycol diethyl ether, diethylene glycol dipropyl ether, or diethylene glycol dibutyl ether; alkylene glycol alkyl ether acetates, such as methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, or propylene glycol monopropyl ether acetate. Alkoxyalkyl acetates, such as methoxybutyl acetate or methoxypentyl acetate; aromatic hydrocarbons, such as benzene, toluene, xylene, or mesitylene; ketones, such as methyl ethyl ketone, acetone, methyl pentyl ketone, methyl isobutyl ketone, or cyclohexanone; alcohols, such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, or glycerol; esters, such as ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, or ethyl 3-phenylpropionate; cyclic esters, such as γ-butyrolactone; methoxybenzene (also known as anisole or fenestrate); or any combination thereof.

[0170] In this embodiment, the solvent may be methoxybenzene (also known as anisole or methyl ether).

[0171] In one implementation, cross-linking of the quantum dot-containing material can be achieved by exposure to ultraviolet light.

[0172] Because the organic groups chemically bonded to the surface of quantum dots in quantum dot-containing materials include azide groups, photocrosslinking reactions may occur. Therefore, the stability of quantum dot-containing materials can be improved. Since the organic groups may include charge-transporting groups, and these charge-transporting groups do not have to be unsubstituted phenyl groups, the mixing between the emitter layer and the hole transport region can be reduced, thus improving the efficiency of quantum dot-containing materials.

[0173] Due to cross-linking bonds, cross-linked materials containing quantum dots can improve stability and efficiency. Therefore, light-emitting devices, such as organic light-emitting devices, can exhibit high or improved hole mobility and long or improved lifetime.

[0174] A light-emitting device including cross-linked material 132 may include:

[0175] First electrode;

[0176] The second electrode facing the first electrode; and

[0177] An intermediate layer between the first and second electrodes, including the emission layer.

[0178] The light-emitting device may include cross-linked materials.

[0179] In some embodiments, the emitter layer may include a cross-linked material.

[0180] In this implementation, the emitting layer can emit red light.

[0181] According to one embodiment, the electronic device may include a light-emitting device. The electronic device may further include a thin-film transistor.

[0182] In an embodiment, the electronic device may further include a thin-film transistor, which includes a source electrode and a drain electrode, and a first electrode of the light-emitting device may be electrically connected to the source electrode or the drain electrode.

[0183] In some embodiments, the electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof. In some embodiments, the electronic device may be a flat panel display device, but the embodiments are not limited thereto.

[0184] Electronic devices can be understood by referring to the description of electronic devices provided in this article.

[0185] Figure 3 Description

[0186] Figure 3 This is a schematic view of a light-emitting device 10 according to an embodiment. The light-emitting device 10 may include a first electrode 110, an intermediate layer 130, and a second electrode 150.

[0187] In the following text, we will combine Figure 3 The structure of the light-emitting device 10 according to the embodiment and the method of preparing the light-emitting device 10 according to the embodiment are described.

[0188] First electrode 110

[0189] exist Figure 3 In this configuration, the substrate may additionally be located below the first electrode 110 or above the second electrode 150. The substrate may be a glass substrate or a plastic substrate. The substrate may be a flexible substrate comprising plastics with excellent heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.

[0190] The first electrode 110 can be formed by depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, a high work function material that can be easily injected with holes can be used as the material for the first electrode.

[0191] The first electrode 110 can be a reflective electrode, a semi-transparent electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, the material used to form the first electrode 110 can be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. In embodiments, when the first electrode 110 is a semi-transparent electrode or a reflective electrode, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof can be used as the material for forming the first electrode 110.

[0192] The first electrode 110 may have a single-layer structure comprising a single layer, or a multi-layer structure comprising two or more layers. In an embodiment, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO.

[0193] Middle layer 130

[0194] Intermediate layer 130 may be on first electrode 110. Intermediate layer 130 may include emitter layer.

[0195] The intermediate layer 130 may include a crosslinked material 132.

[0196] The intermediate layer 130 may further include a hole transport region between the first electrode 110 and the emitter layer and an electron transport region between the emitter layer and the second electrode 150.

[0197] In addition to various organic materials, the intermediate layer 130 may further include metal-containing compounds (such as organometallic compounds), inorganic materials (such as quantum dots), and the like.

[0198] The intermediate layer 130 may include: i) at least two light-emitting units sequentially stacked between the first electrode 110 and the second electrode 150, and ii) a charge-generating layer located between the at least two light-emitting units. While not wishing to be bound by theory, it is to be understood that when the intermediate layer 130 includes at least two light-emitting units and a charge-generating layer, the light-emitting device 10 may be a series-connected light-emitting device.

[0199] Hole transport region in intermediate layer 130

[0200] The hole transport region may have: i) a single-layer structure comprising a single layer of a single material, ii) a single-layer structure comprising a single layer of multiple different materials, or iii) a multi-layer structure comprising multiple layers of multiple different materials.

[0201] The hole transport region may include a hole injection layer (HIL), a hole transport layer (HTL), an emission assist layer, an electron blocking layer (EBL), or a combination thereof.

[0202] For example, the hole transport region may have a multilayer structure, such as a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission auxiliary layer structure, a hole injection layer / emission auxiliary layer structure, a hole transport layer / emission auxiliary layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure, wherein the layers of each structure are stacked on the first electrode 110 in the order stated therein.

[0203] The hole transport region may include the compound represented by Formula 201, the compound represented by Formula 202, or any combination thereof:

[0204] Formula 201

[0205]

[0206] Formula 202

[0207]

[0208] In Equations 201 and 202,

[0209] L 201 To L 204 Each can be independently of being unreplaced or by at least one R.10a Replacement C3-C 60 The carbocyclic group, or the unsubstituted group or the group with at least one R 10a Replacement C1-C 60 Heterocyclic groups,

[0210] L 205 It can be *-O-*', *-S-*', or *-N(Q) 201 )-*', not replaced or replaced by at least one R 10a Replacement C1-C 20 Alkylene, unsubstituted or with at least one R 10a Replacement C2-C 20 Sub-alkenyl groups, unsubstituted or with at least one R 10a Replacement C3-C 60 The carbocyclic group, or the unsubstituted group or the group with at least one R 10a Replacement C1-C 60 Heterocyclic groups,

[0211] xa1 to xa4 can each be an integer from 0 to 5 independently.

[0212] xa5 can be an integer from 1 to 10.

[0213] R 201 To R 204 And Q 201 Each can be independently of being unreplaced or by at least one R. 10a Replacement C3-C 60 The carbocyclic group, or the unsubstituted group or the group with at least one R 10a Replacement C1-C 60 Heterocyclic groups,

[0214] R 201 and R 202 They may optionally be bonded to each other via: single bonds, unsubstituted bonds, or bonds with at least one R group. 10a Substituted C1-C5 alkylene groups, or unsubstituted or substituted with at least one R 10a Substituted C2-C5 sub-alkenyl groups to form unsubstituted or substituted groups with at least one R group 10a Replacement C8-C 60 Polycyclic groups (e.g., carbazole groups or similar groups) (e.g., compound HT16 described herein),

[0215] R 203 and R 204 They may optionally be bonded to each other via: single bonds, unsubstituted bonds, or bonds with at least one R group. 10a Substituted C1-C5 alkylene groups, or unsubstituted or substituted with at least one R 10aSubstituted C2-C5 sub-alkenyl groups to form unsubstituted or substituted groups with at least one R group 10a Replacement C8-C 60 Polycyclic groups, and

[0216] na1 can be an integer from 1 to 4.

[0217] In embodiments, formulas 201 and 202 may each include at least one of the groups represented by formulas CY201 to CY217:

[0218]

[0219] In formulas CY201 to CY217, R 10b and R 10c Each can refer to R. 10a To understand from the description, CY 201 To CY 204 Each can be independently C3-C 20 Carbocyclic groups or C1-C 20 Heterocyclic groups, and at least one hydrogen in formulas CY201 to CY217 may be unsubstituted or R 10a replace.

[0220] In the implementation, in formulas CY201 to CY217, the ring CY 201 To CY 204 Each can be independently phenyl, naphthyl, phenanthryl or anthracene.

[0221] In an embodiment, formula 201 and formula 202 may each include at least one of the groups represented by formulas CY201 to CY203.

[0222] In an embodiment, formula 201 may include at least one of the groups represented by formulas CY201 to CY203 or at least one of the groups represented by formulas CY204 to CY217.

[0223] In the implementation, in formula 201, xa1 can be 1, R 201 It can be any group represented by formula CY201 to CY203, xa2 can be 0, and R 202 It can be any group represented by any one of the formulas CY204 to CY207.

[0224] In an embodiment, formulas 201 and 202 may each exclude groups represented by formulas CY201 to CY203.

[0225] In an embodiment, Formula 201 and Formula 202 may each exclude the groups represented by Formulas CY201 to CY203, and include at least one of the groups represented by Formulas CY204 to CY217.

[0226] In an embodiment, formulas 201 and 202 may each exclude groups represented by formulas CY201 to CY217.

[0227] In an embodiment, the hole transport region may include one or any combination of compounds HT1 to HT46 or m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4”-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonic acid) (PANI / PSS);

[0228]

[0229]

[0230]

[0231]

[0232]

[0233] The thickness of the hole transport region can be approximately to approximately Within the range, for example, approximately to approximately about to approximately about to approximately about to approximately about to approximately about to approximately about to approximately about to approximately and about to approximately When the hole transport region includes a hole injection layer, a hole transport layer, and any combination thereof, the thickness of the hole injection layer can be approximately [missing information]. to approximately Within the range, for example, approximately to approximately about to approximately about to approximately about to approximately and about to approximately to approximately to approximately to approximately to approximately or to approximately The thickness of the hole transport layer can be approximately to approximately Within the range, for example, approximately to approximately about to approximately and about to approximately While we don't want to be bound by theory, it's important to understand that when the thicknesses of the hole transport region, hole injection layer, and hole transport layer are all within these ranges, excellent or improved hole transport characteristics can be obtained without significantly increasing the driving voltage.

[0234] The emission assist layer can improve luminous efficiency by compensating for the optical resonant distance according to the wavelength of the light emitted by the emission layer. The electron blocking layer can reduce or eliminate electron flow from the electron transport region. The emission assist layer and the electron blocking layer can include the materials described above.

[0235] p-type dopant

[0236] The hole transport region may include a charge-generating material and the aforementioned materials to improve the conductivity of the hole transport region. The charge-generating material may be substantially uniformly or non-uniformly dispersed in the hole transport region (e.g., as a monolayer comprising the charge-generating material).

[0237] For example, charge-generating materials may include p-type dopants.

[0238] In an implementation, the lowest unoccupied molecular orbital (LUMO) level of the p-type dopant may be about -3.5 electron volts (eV) or less.

[0239] In embodiments, p-type dopants may include quinone derivatives, compounds containing cyano groups, compounds containing elements EL1 and EL2, or any combination thereof.

[0240] Examples of quinone derivatives may include TCNQ, F4-TCNQ, and analogs.

[0241] Examples of compounds containing a cyano group include HAT-CN, compounds represented by formula 221, and analogues:

[0242]

[0243] Equation 221

[0244]

[0245] In Equation 221,

[0246] R 221 To R 223 Each can be independently of being unreplaced or by at least one R. 10a Replacement C3-C 60 The carbocyclic group, or the unsubstituted group or the group with at least one R 10a Replacement C1-C 60 Heterocyclic groups, and

[0247] R 221 To R 223 At least one of them can be C3-C independently. 60 Carbocyclic groups or C1-C 60 Heterocyclic groups, each independently substituted by the following groups: cyano; -F; -Cl; -Br; -I; C1-C substituted with cyano, -F, -Cl, -Br, -I or any combination thereof. 20 Alkyl groups; or any combination thereof.

[0248] In compounds containing elements EL1 and EL2, element EL1 may be a metal, a metalloid, or a combination thereof, and element EL2 may be a nonmetal, a metalloid, or a combination thereof.

[0249] Examples of metals may include: alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), or the like); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), or the like); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), and cobalt (Co). Rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), or the like; later transition metals (e.g., zinc (Zn), indium (In), tin (Sn), or the like); lanthanides (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), or the like); and the like.

[0250] Examples of metalloids may include silicon (Si), antimony (Sb), tellurium (Te), and the like.

[0251] Examples of nonmetals may include oxygen (O), halogens (e.g., F, Cl, Br, I and the like) and the like.

[0252] For example, compounds containing elements EL1 and EL2 may include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides, metal iodides, and the like), metal halide-like compounds (e.g., metal fluoride-like compounds, metal chloride-like compounds, metal bromide-like compounds, metal iodide-like compounds, and the like), metal tellurides, or any combination thereof.

[0253] Examples of metal oxides may include: tungsten oxides (e.g., WO, W2O3, WO2, WO3, W2O5 and the like), vanadium oxides (e.g., VO, V2O3, VO2, V2O5 and the like), molybdenum oxides (MoO, Mo2O3, MoO2, MoO3, Mo2O5 and the like), rhenium oxides (e.g., ReO3 and the like) and the like.

[0254] Examples of metal halides may include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, lanthanide metal halides, and the like.

[0255] Examples of alkali metal halides may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, CsI, and the like.

[0256] Examples of alkaline earth metal halides may include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, BaI2 and the like.

[0257] Examples of transition metal halides may include: titanium halides (e.g., TiF4, TiCl4, TiBr4, TiI4 and the like), zirconium halides (e.g., ZrF4, ZrCl4, ZrBr4, ZrI4 and the like), hafnium halides (e.g., HfF4, HfCl4, HfBr4, HfI4 and the like), vanadium halides (e.g., VF3, VCl3, VBr3, VI3 and the like), niobium halides (e.g., NbF3, NbCl3, NbBr3, NbI3 and the like), and tantalum halides (e.g., TaF3, TaCl3, TaBr3). TaI3 and the like), chromium halides (e.g., CrF3, CrCl3, CrBr3, CrI3 and the like), molybdenum halides (e.g., MoF3, MoCl3, MoBr3, MoI3 and the like), tungsten halides (e.g., WF3, WCl3, WBr3, WI3 and the like), manganese halides (e.g., MnF2, MnCl2, MnBr2, MnI2 and the like), technetium halides (e.g., TcF2, TcCl2, TcBr2, TcI2 and the like), rhenium halides (e.g., ReF2, ReCl2, ReBr2, ReI... 2 and similar compounds), iron halides (e.g., FeF2, FeCl2, FeBr2, FeI2 and similar compounds), ruthenium halides (e.g., RuF2, RuCl2, RuBr2, RuI2 and similar compounds), osmium halides (e.g., OsF2, OsCl2, OsBr2, OsI2 and similar compounds), cobalt halides (e.g., CCoF2, CoCl2, CoBr2, CoI2 and similar compounds), rhodium halides (e.g., RhF2, RhCl2, RhBr2, RhI2 and similar compounds), iridium halides (e.g., IrF2, IrCl2, IrBr2, I... rI2 and the like), nickel halides (e.g., NiF2, NiCl2, NiBr2, NiI2 and the like), palladium halides (e.g., PdF2, PdCl2, PdBr2, PdI2 and the like), platinum halides (e.g., PtF2, PtCl2, PtBr2, PtI2 and the like), copper halides (e.g., CuF, CuCl, CuBr, CuI and the like), silver halides (e.g., AgF, AgCl, AgBr, AgI and the like), gold halides (e.g., AuF, AuCl, AuBr, AuI and the like) and the like.

[0258] Examples of post-transition metal halides may include zinc halides (e.g., ZnF2, ZnCl2, ZnBr2, ZnI2 and the like), indium halides (e.g., InI3 and the like), tin halides (e.g., SnI2 and the like) and the like.

[0259] Examples of lanthanide metal halides may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, SmI3 and the like.

[0260] Examples of metal halide-like compounds may include antimony halides (e.g., SbCl5 and the like) and their analogues.

[0261] Examples of metal tellurides may include: alkali metal tellurides (e.g., Li₂Te, Na₂Te, K₂Te, Rb₂Te, Cs₂Te and the like), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe, BaTe and the like), and transition metal tellurides (e.g., TiTe₂, ZrTe₂, HfTe₂, V₂Te₃, Nb₂Te₃, Ta₂Te₃, Cr₂Te₃, Mo₂Te₃, W₂Te₃, MnTe, TcTe, ReTe, FeTe). RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe, Au2Te and the like), post-transition metal tellurides (e.g., ZnTe and the like), lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe and the like) and the like.

[0262] emission layer in intermediate layer 130

[0263] When the light-emitting device 10 is a full-color light-emitting device, the emitting layer can be patterned as a red emitting layer, a green emitting layer, and / or a blue emitting layer, depending on the sub-pixel. In an embodiment, the emitting layer may have a stacked structure. The stacked structure may include two or more layers selected from the red, green, and blue emitting layers. The two or more layers may be in direct contact with each other. In an embodiment, the two or more layers may be separated from each other. In an embodiment, the emitting layer may include two or more materials. The two or more materials may include red, green, or blue emitting materials. The two or more materials may be mixed in a single layer. The two or more materials mixed in a single layer may emit white light.

[0264] The emitter layer may include cross-linked material 132.

[0265] The emitting layer may further include a host and a dopant. The dopant may be a phosphorescent dopant, a fluorescent dopant, or any combination thereof.

[0266] Based on a total of 100 parts by weight of the main body, the amount of dopant in the emitter layer can range from about 0.01 parts by weight to about 15 parts by weight, for example, from about 0.01 parts by weight to about 12 parts by weight, from about 0.01 parts by weight to about 10 parts by weight, from about 0.01 parts by weight to about 8 parts by weight, from about 0.01 parts by weight to about 6 parts by weight, from about 0.01 parts by weight to about 4 parts by weight, from about 0.01 parts by weight to about 2 parts by weight, from about 0.01 parts by weight to about 1 part by weight, from about 1 part by weight to about 15 parts by weight, from about 5 parts by weight to about 15 parts by weight, and from about 10 parts by weight to about 15 parts by weight.

[0267] In some implementations, the emitter layer may further include quantum dots.

[0268] The emission layer may further include a delayed fluorescence material. The delayed fluorescence material may act as a host or dopant in the emission layer.

[0269] The thickness of the emission layer can be approximately to approximately Within the scope, and in some implementations, approximately to approximately about to approximately about to approximately about to approximately or about to approximately While we don't want to be bound by theory, it's important to understand that improved light emission characteristics can be obtained without significantly increasing the driving voltage when the thickness of the emitting layer is within any of these ranges.

[0270] main body

[0271] The main body may include compounds represented by formula 301:

[0272] Formula 301

[0273] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21

[0274] In Equation 301,

[0275] Ar 301 and L 301 Each can be independently defined as: not replaced or replaced by at least one R. 10a Replacement C3-C 60 The carbocyclic group, or the unsubstituted group or the group with at least one R 10aReplacement C1-C 60 Heterocyclic groups,

[0276] xb11 can be 1, 2, or 3.

[0277] xb1 can be an integer from 0 to 5.

[0278] R 301 It can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl thio group, unsubstituted or with at least one R 10a Replacement C3-C 60 Carbocyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -Si(Q) 301 (Q) 302 (Q) 303 -N(Q) 301 (Q) 302 -B(Q) 301 (Q) 302 -C(=O)(Q) 301 -S(=O)2(Q) 301 ) or -P(=O)(Q 301 (Q) 302 ),

[0279] xb21 can be an integer from 1 to 5, and

[0280] Among them, Q 301 To Q 303 Each can be understood by referring to the description of Q1 provided in this article.

[0281] In the implementation, when xb11 in equation 301 is 2 or greater, at least two Ar 301 It can be linked via a single bond.

[0282] In embodiments, the main body may include a compound represented by formula 301-1, a compound represented by formula 301-2, or any combination thereof:

[0283] Formula 301-1

[0284]

[0285] Formula 301-2

[0286]

[0287] Among them, in equations 301-1 and 301-2,

[0288] Ring A 301 To Ring A 304 Each can be independently defined as: not replaced or replaced by at least one R. 10a Replacement C3-C 60 The carbocyclic group, or the unsubstituted group or the group with at least one R 10a Replacement C1-C 60 Heterocyclic groups,

[0289] X 301 Can be O, S, N-[(L 304 ) xb4 -R 304 ]、C(R 304 (R) 305 ) or Si(R 304 (R) 305 ),

[0290] xb22 and xb23 can each be 0, 1, or 2 independently.

[0291] L 301 xb1 and R 301 You can refer to the L provided in this article respectively 301 xb1 and R 301 To understand from the description,

[0292] L 302 To L 304 You can refer to the L provided in this article respectively 301 To understand from the description,

[0293] xb2 to xb4 can be understood by referring to the description of xb1 provided in this document, and

[0294] R 302 To R 305 and R 311 To R 314 Each can refer to the R provided in this article. 301 To understand this, we need to refer to the description.

[0295] In embodiments, the host may include an alkaline earth metal complex. For example, the host may include a Be complex (e.g., compound H55), a Mg complex, a Zn complex, or any combination thereof.

[0296] In embodiments, the main body may include one or any combination of compounds H1 to H124, 9,10-bis(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthyl-2-yl)anthracene (MADN), 9,10-bis-(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-bis-9-carbazolylbenzene (mCP), and 1,3,5-tris(carbazolyl-9-yl)benzene (TCP).

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304] Phosphorescent dopants

[0305] Phosphorescent dopants may include at least one transition metal as the center metal.

[0306] Phosphorescent dopants may include monodentate ligands, bidentate ligands, tridentate ligands, tetradentate ligands, pentadentate ligands, hexadentate ligands, or any combination thereof.

[0307] Phosphorescent dopants can be electrically neutral.

[0308] In an embodiment, the phosphorescent dopant may include an organometallic complex represented by formula 401:

[0309] Formula 401

[0310] M(L 401 ) xc1 (L 402 ) xc2

[0311] Among them, L 401 It can be a ligand represented by Equation 402.

[0312] Formula 402

[0313]

[0314] In Equations 401 and 402,

[0315] M can be a transition metal (e.g., iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), and thulium (Tm)).

[0316] xc1 can be 1, 2, or 3, and when xc1 is 2 or greater, at least two L's are required. 401 They can be the same or different from each other.

[0317] L 402 It can be an organic ligand, and xc2 can be an integer from 0 to 4, and when xc2 is 2 or greater, at least two L... 402 They can be the same or different from each other.

[0318] X 401 To X 402 They can be nitrogen or carbon independently.

[0319] Ring A 401 And Ring A 402 Each can be independently C3-C 60 Carbocyclic groups or C1-C 60 Heterocyclic groups,

[0320] T 401 It can be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q) 411 )-*'、*-C(Q 411 (Q) 412 )-*'、*-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 ) = *' or * = C = *',

[0321] X 403 and X 404 Each can be an independent chemical bond (e.g., covalent or coordinate), O, S, N (Q) 413 ), B(Q) 413 ), P(Q 413 ), C(Q 413 (Q) 414 ) or Si(Q 413 (Q) 414 ),

[0322] Q 411 To Q 414Each can be understood by referring to the description of Q1 provided in this article.

[0323] R 401 and R 402 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 20 Alkyl, unsubstituted or with at least one R 10a Replacement C1-C 20 Alkyl group, unsubstituted or with at least one R 10a Replacement C1-C 20 Alkyl thio group, unsubstituted or with at least one R 10a Replacement C3-C 60 Carbocyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -Si(Q) 401 (Q) 402 (Q) 403 -N(Q) 401 (Q) 402 -B(Q) 401 (Q) 402 -C(=O)(Q) 401 -S(=O)2(Q) 401 ) or -P(=O)(Q 401 (Q) 402 ),

[0324] Q 401 To Q 403 Each can be understood by referring to the description of Q1 provided in this article.

[0325] xc11 and xc12 can each be an integer from 0 to 10 independently, and

[0326] In Equation 402, * and *' each indicate the binding site with M in Equation 401.

[0327] In the implementation, in equation 402, i)X 401 It can be nitrogen, and X 402 It can be carbon, or ii)X 401 and X 402 Both of them are nitrogen.

[0328] In the implementation, when xc1 in equation 401 is 2 or greater, at least two L 401 The two rings A in 401 Optionally via T 402 As a linking group; or two A's 402Optionally via T 403 It is bound as a linking group (see compounds PD1 through PD4 and PD7). T 402 and T 403 Each can refer to the T provided in this article. 401 To understand from the description,

[0329] L in Equation 401 402 It can be any suitable organic ligand. For example, L 402 It can be a halogen, a diketone group (e.g., an acetylacetone group), a carboxylic acid group (e.g., a pyridine carboxylate group), -C (=O), an isonitrile group, -CN, or a phosphorus-containing group (e.g., a phosphine group or a phosphite group).

[0330] The phosphorescent dopant may be, for example, one of compounds PD1 to PD25, or any combination thereof:

[0331]

[0332]

[0333] Fluorescent dopants

[0334] Fluorescent dopants may include compounds containing amine groups, compounds containing styrene groups, or any combination thereof.

[0335] In an embodiment, the fluorescent dopant may include a compound represented by formula 501:

[0336] Formula 501

[0337]

[0338] In Equation 501,

[0339] Ar 501 L 501 To L 503 R 501 and R 502 Each can be independently defined as: not replaced or replaced by at least one R. 10a Replacement C3-C 60 The carbocyclic group, or the unsubstituted group or the group with at least one R 10a Replacement C1-C 60 Heterocyclic groups,

[0340] xd1 to xd3 can each be independently 0, 1, 2, or 3, and

[0341] xd4 can be 1, 2, 3, 4, 5 or 6.

[0342] In the implementation, in formula 501, Ar501 It may include fused-ring groups in which at least three monocyclic groups are fused together (e.g., anthracene, ...). (Base or pyrene group).

[0343] In an implementation, xd4 in Equation 501 can be 2.

[0344] In this embodiment, the fluorescent dopant may include one or any combination of compounds FD1 to FD36, DPVBi, DPAVBi, etc.

[0345]

[0346]

[0347]

[0348] Delayed fluorescence materials

[0349] The emission layer may include a delayed fluorescence material.

[0350] The delayed fluorescence material described in this article can be any suitable compound that emits delayed fluorescence based on the delayed fluorescence emission mechanism.

[0351] The delayed fluorescence material included in the emission layer can act as a host or a dopant, depending on the type of other materials included in the emission layer.

[0352] In this embodiment, the difference between the triplet energy level (eV) and the singlet energy level (eV) of the delayed fluorescent material can be greater than or equal to about 0 eV and less than or equal to about 0.5 eV. While not wishing to be bound by theory, it is understood that when the difference between the triplet energy level (eV) and the singlet energy level (eV) of the delayed fluorescent material is within this range, the upconversion from the triplet to the singlet state in the delayed fluorescent material can occur effectively, thus improving the luminous efficiency and similar performance of the light-emitting device 10.

[0353] In embodiments, delayed fluorescence materials may include: i) at least one electron donor (e.g., π-electron-rich C3-C). 60 Cyclic groups, such as carbazole groups and analogs, and at least one electron acceptor (e.g., sulfoxide, cyano, nitrogen-containing C1-C lacking π electrons). 60 Materials comprising (i) cyclic groups and analogues, and (ii) C8-C cyclic groups comprising at least two cyclic groups fused together and sharing boron (B). 60 Materials with polycyclic groups, and analogues.

[0354] Examples of delayed fluorescence materials may include at least one of compounds DF1 to DF9:

[0355]

[0356] quantum dots

[0357] The emission layer may include quantum dots.

[0358] The emission layer may include a material 131 containing quantum dots.

[0359] The quantum dot-containing material 131 may include quantum dots 131A and organic groups 131B.

[0360] The emission layer may include a material 131 containing quantum dots, and may further include different quantum dots.

[0361] The quantum dots used in this article may include quantum dot 131A or different quantum dots.

[0362] The term “quantum dot” as used herein refers to a crystal of a semiconductor compound and may include any suitable material capable of emitting wavelengths of various lengths depending on the size of the crystal.

[0363] The diameter of quantum dots can be in the range of, for example, about 1 nm to about 10 nm, such as about 1 nm to about 8 nm, about 1 nm to about 6 nm, about 1 nm to about 4 nm, about 1 nm to about 2 nm, about 3 nm to about 10 nm, about 5 nm to about 10 nm, about 7 nm to about 10 nm, and about 9 nm to about 10 nm.

[0364] Quantum dots can be synthesized by wet chemical methods, organometallic chemical vapor deposition, molecular beam epitaxy, or any similar methods.

[0365] The wet chemical method is a process of growing quantum dot particles by mixing precursor materials with an organic solvent. During crystal growth, the organic solvent naturally acts as a dispersant on the surface of the quantum dot crystals and controls the crystal growth. Therefore, the wet chemical method may be easier to perform than processes such as metal-organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE). Furthermore, the growth of quantum dot particles can be controlled at a lower manufacturing cost.

[0366] Quantum dots may include: group III-VI semiconductor compounds; group II-VI semiconductor compounds; group III-V semiconductor compounds; group III-VI semiconductor compounds; group I-III-VI semiconductor compounds; group IV-VI semiconductor compounds; group IV elements or compounds; or any combination thereof.

[0367] Examples of group II-VI semiconductor compounds may include: binary compounds such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, or MgS; ternary compounds such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, C dZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe or MgZnS; quaternary compounds such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe or HgZnSTe; or any combination thereof.

[0368] Examples of Group III-V semiconductor compounds may include: binary compounds such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, or InSb; ternary compounds such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, or InPSb; quaternary compounds such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, or InAlPSb; or any combination thereof. In embodiments, the Group III-V semiconductor compounds may further include Group II elements. Examples of group III-V semiconductor compounds that further include group II elements may include InZnP, InGaZnP, InAlZnP, and the like.

[0369] Examples of group III-VI semiconductor compounds may include: binary compounds such as GaS, GaSe, Ga2Se3, GaTe, InS, In2S3, InSe, In2Se3, InTe and the like; ternary compounds such as InGaS3, InGaSe3 and the like; or any combination thereof.

[0370] Examples of group I-III-VI semiconductor compounds may include ternary compounds such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, AgAlO2, or any combination thereof.

[0371] Examples of group IV-VI semiconductor compounds may include: binary compounds, such as SnS, SnSe, SnTe, PbS, PbSe, or PbTe; ternary compounds, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, or SnPbTe; quaternary compounds, such as SnPbSSe, SnPbSeTe, or SnPbSTe; or any combination thereof.

[0372] Element IV or the compound may be: a single element, such as Si or Ge; a binary compound, such as SiC or SiGe; or any combination thereof.

[0373] Individual elements in multi-element compounds (such as binary, ternary, and quaternary compounds) may exist in their particles at uniform or non-uniform concentrations.

[0374] Quantum dots can have a monolayer structure in which the concentration of each element contained in the quantum dot is uniform, or a core-shell bilayer structure. In some embodiments, the material contained in the core may be different from the material contained in the shell.

[0375] The shell of a quantum dot can: serve as a protective layer to prevent chemical denaturation of the nucleus and maintain semiconductor properties, and / or serve as a charging layer to impart electrophoretic properties to the quantum dot. The shell can be single-layered or multi-layered. The interface between the nucleus and the shell can have a concentration gradient, wherein the concentration of elements present in the shell can decrease towards the nucleus.

[0376] Examples of shells for quantum dots include metal oxides or nonmetal oxides, semiconductor compounds, or combinations thereof. Examples of metal oxides or nonmetal oxides may include: binary compounds such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, or NiO; ternary compounds such as MgAl2O4, CoFe2O4, NiFe2O4, or CoMn2O4; and any combination thereof. Examples of semiconductor compounds may include: Group III-VI semiconductor compounds; Group II-VI semiconductor compounds; Group III-V semiconductor compounds; Group III-VI semiconductor compounds; Group I-III-VI semiconductor compounds; Group IV-VI semiconductor compounds; or any combination thereof. In embodiments, the semiconductor compound may be CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.

[0377] Quantum dots can have a full width at half maximum (FWHM) of a spectrum with emission wavelengths of about 45 nm or less, about 40 nm or less, or about 30 nm or less. When the FWHM of a quantum dot is within this range, color purity or color reproducibility can be improved. In implementations, because light emitted through quantum dots is emitted in all directions, the optical viewing angle can be improved.

[0378] In implementation, quantum dots may specifically be spherical, pyramidal, multi-armed, or cubic nanoparticles, nanotubes, nanowires, nanofibers, or nanoplate particles.

[0379] By adjusting the size of the quantum dots, the band gap can also be adjusted, thereby obtaining light of various wavelengths in the quantum dot emission layer. By using quantum dots of various sizes, light-emitting devices capable of emitting light of various wavelengths can be realized. In one embodiment, the size of the quantum dots can be selected so that they can emit red, green, and / or blue light. In another embodiment, the size of the quantum dots can be selected so that they can emit white light by combining various colors of light.

[0380] Electron transport region in intermediate layer 130

[0381] The electron transport region may have: i) a single-layer structure comprising a single layer of a single material, ii) a single-layer structure comprising a single layer of multiple different materials, or iii) a multi-layer structure comprising multiple layers of multiple different materials.

[0382] The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or an electron injection layer.

[0383] In an embodiment, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein the layers of each structure may be stacked on the emitter layer in the order stated therein.

[0384] Electron transport regions (e.g., buffer layers, hole blocking layers, electron control layers, or electron transport layers within electron transport regions) may include at least one nitrogen-containing C1-C element lacking π electrons. 60 Metal-free compounds with cyclic groups.

[0385] In an embodiment, the electron transport region may include a compound represented by formula 601:

[0386] Formula 601

[0387] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21

[0388] In Equation 601,

[0389] Ar 601 and L 601 Each can be independently defined as: not replaced or replaced by at least one R. 10a Replacement C3-C 60 The carbocyclic group, or the unsubstituted group or the group with at least one R 10a Replacement C1-C 60 Heterocyclic groups,

[0390] xe11 can be 1, 2, or 3.

[0391] xe1 can be 0, 1, 2, 3, 4, or 5.

[0392] R 601 It can be either not replaced or replaced by at least one R 10a Replacement C3-C 60 Carbocyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -Si(Q) 601 (Q) 602 (Q) 603 -C(=O)(Q) 601 -S(=O)2(Q)601 ) or -P(=O)(Q 601 (Q) 602 ),

[0393] Q 601 To Q 603 Each can be understood by referring to the description of Q1 provided in this article.

[0394] xe21 can be 1, 2, 3, 4, or 5, and

[0395] Ar 601 L 601 and R 601 At least one of them can be independently unsubstituted or by at least one R. 10a Substituted C1-C lacking π electrons and containing nitrogen 60 Cyclic groups.

[0396] In the implementation, when xe11 in formula 601 is 2 or greater, at least two Ar 601 It can be linked via a single bond.

[0397] In the implementation, in formula 601, Ar 601 It can be an anthracene group that has been substituted or not.

[0398] In an embodiment, the electron transport region may include a compound represented by formula 601-1:

[0399] Formula 601-1

[0400]

[0401] In Equation 601-1,

[0402] X 614 It can be N or C(R) 614 ), X 615 It can be N or C(R) 615 ), X 616 It can be N or C(R) 616 ), X 614 To X 616 At least one of them can be N,

[0403] L 611 To L 613 You can refer to the L provided in this article 601 To understand from the description,

[0404] xe611 to xe613 can each be understood by referring to the description of xe1 provided in this document.

[0405] R 611 To R 613Each can refer to the R provided in this article. 601 To understand from the description, and

[0406] R 614 To R 616 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkyl thio group, unsubstituted or with at least one R 10a Replacement C3-C 60 The carbocyclic group, or the unsubstituted group or the group with at least one R 10a Replacement C1-C 60 Heterocyclic groups.

[0407] For example, in Equations 601 and 601-1, xe1 and xe611 to xe613 can each be 0, 1 or 2 independently.

[0408] The electron transport region may include one or any combination of compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, TAZ, and NTAZ:

[0409]

[0410]

[0411]

[0412]

[0413] The thickness of the electron transport region can be approximately to approximately Within the range, for example, approximately to approximately about to approximately about to approximately about to approximately about to approximately and about to approximately When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thicknesses of the buffer layer, the hole blocking layer, and the electron control layer can each be independently set to approximately [missing information]. to approximately Within the range, for example, approximately to approximately about to approximately about to approximately about to approximately about to approximately about to approximately about to approximately and about to approximately Furthermore, the thickness of the electron transport layer can be approximately to approximately Within the range, for example, approximately to approximately about to approximately about to approximately about to approximately and about to approximately While we do not wish to be bound by theory, it is important to understand that when the thicknesses of the buffer layer, hole blocking layer, electron control layer, electron transport layer, and / or electron transport region are each within these ranges, excellent or improved electron transport characteristics can be obtained without significantly increasing the driving voltage.

[0414] In addition to the materials mentioned above, the electron transport region (e.g., the electron transport layer in the electron transport region) may further include a material containing metal.

[0415] Materials containing metals may include alkali metal complexes, alkaline earth metal complexes, or any combination thereof. The metal ions in alkali metal complexes may be lithium (Li) ions, sodium (Na) ions, potassium (K) ions, rubidium (Rb) ions, or cesium (Cs) ions. The metal ions in alkaline earth metal complexes may be beryllium (Be) ions, magnesium (Mg) ions, calcium (Ca) ions, strontium (Sr) ions, or barium (Ba) ions. Each ligand coordinated to the metal ion of the alkali metal complex or alkaline earth metal complex may independently be hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.

[0416] For example, materials containing metals may include Li complexes. Li complexes may include, for example, compounds ET-D1 (LiQ) or ET-D2:

[0417]

[0418] The electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 150. The electron injection layer may be in direct contact with the second electrode 150.

[0419] The electron injection layer may have: i) a single-layer structure including a single layer containing a single material, ii) a single-layer structure including a single layer containing multiple different materials, or iii) a multi-layer structure including multiple layers containing multiple different materials.

[0420] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, a compound containing an alkali metal, a compound containing an alkaline earth metal, a compound containing a rare earth metal, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

[0421] The alkali metal may be Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may be Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may be Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.

[0422] The compound containing an alkali metal, the compound containing an alkaline earth metal, and the compound containing a rare earth metal may be an oxide, a halide (e.g., fluoride, chloride, bromide, or iodide), a telluride, or any combination thereof of each of the alkali metal, the alkaline earth metal, and the rare earth metal, respectively.

[0423] The compound containing an alkali metal may be an alkali metal oxide (such as Li2O, Cs2O, or K2O), an alkali metal halide (such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI), or any combination thereof. The compound containing an alkaline earth metal may include alkaline earth metal compounds such as BaO, SrO, CaO, Ba x Sr 1-x O (where x is a real number satisfying 0 < x < 1) or Ba x Ca 1-xO (where x is a real number satisfying 0 < x < 1). The compound containing a rare earth metal may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof. In an embodiment, the compound containing a rare earth metal may include a lanthanide metal telluride. Examples of the lanthanide metal telluride may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, Lu2Te3, and the like.

[0424] The alkali metal complex, alkaline earth metal complex, and rare earth metal complex may include: i) one of the ions of the alkali metal, alkaline earth metal, and rare earth metal described above; and ii) a ligand bound to the metal ion, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.

[0425] The electron injection layer may include or consist of: the alkali metal, alkaline earth metal, rare earth metal, compound containing an alkali metal, compound containing an alkaline earth metal, compound containing a rare earth metal, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or any combination thereof as described above. In an embodiment, the electron injection layer may further include an organic material (for example, a compound represented by Formula 601).

[0426] In an embodiment, the electron injection layer may include or consist of: i) a compound containing an alkali metal (for example, an alkali metal halide), or ii) a) a compound containing an alkali metal (for example, an alkali metal halide) and b) an alkali metal, alkaline earth metal, rare earth metal, or any combination thereof. In an embodiment, the electron injection layer may be a KI:Yb co-deposited layer, a RbI:Yb co-deposited layer, and similar layers.

[0427] When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, a compound containing an alkali metal, a compound containing an alkaline earth metal, a compound containing a rare earth metal, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof, it may be uniformly or non-uniformly dispersed in a matrix including the organic material.

[0428] The thickness of the electron injection layer can be approximately to approximately Within the scope, and in some implementations, approximately to approximately about to approximately about to approximately about to approximately about to approximately about to approximately about to approximately or about to approximately While we do not wish to be bound by theory, it is important to understand that when the thickness of the electron injection layer is within these ranges, excellent or improved electron injection characteristics can be obtained without significantly increasing the driving voltage.

[0429] Second electrode 150

[0430] The second electrode 150 may be located on the intermediate layer 130. In an embodiment, the second electrode 150 may be a cathode serving as an electron injection electrode. In an embodiment, the material used to form the second electrode 150 may be a material with a low work function, such as a metal, alloy, conductive compound, or any combination thereof.

[0431] The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO, or any combination thereof. The second electrode 150 may be a transmission electrode, a semi-transmission electrode, or a reflection electrode.

[0432] The second electrode 150 may have a single-layer structure or a multi-layer structure including two or more layers.

[0433] Cover layer

[0434] The first cover layer may be located outside the first electrode 110, and / or the second cover layer may be located outside the second electrode 150. In an embodiment, the light-emitting device 10 may have: a structure in which the first cover layer, the first electrode 110, the intermediate layer 130, and the second electrode 150 are stacked in the order stated; a structure in which the first electrode 110, the intermediate layer 130, the second electrode 150, and the second cover layer are stacked in the order stated; or a structure in which the first cover layer, the first electrode 110, the intermediate layer 130, the second electrode 150, and the second cover layer are stacked in the order stated.

[0435] In the light-emitting device 10, light emitted from the emitting layer in the intermediate layer 130 can pass through the first electrode 110 (which may be a semi-transparent electrode or a transmissive electrode) and through the first capping layer to the outside. In the light-emitting device 10, light emitted from the emitting layer in the intermediate layer 130 can pass through the second electrode 150 (which may be a semi-transparent electrode or a transmissive electrode) and through the second capping layer to the outside.

[0436] Based on the principle of constructive interference, the first and second capping layers can improve the external luminous efficiency. In this embodiment, the light extraction efficiency of the light-emitting device 10 can be improved, thereby improving the luminous efficiency of the light-emitting device 10.

[0437] The first and second capping layers may each comprise a material having a refractive index of 1.6 or greater (at 589 nm).

[0438] The first and second covering layers can each be independently a covering layer including organic materials, an inorganic covering layer including inorganic materials, or a composite covering layer including both organic and inorganic materials.

[0439] At least one of the first and second capping layers may independently comprise a carbocyclic compound, a heterocyclic compound, an amino-containing compound, a porphyrin derivative, a phthalocyanine derivative, a naphthylphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, heterocyclic compound, and amino-containing compound may optionally be substituted with substituents of O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In embodiments, at least one of the first and second capping layers may independently comprise an amino-containing compound.

[0440] In an embodiment, at least one of the first and second capping layers may each independently include a compound represented by formula 201, a compound represented by formula 202, or any combination thereof.

[0441] In an embodiment, at least one of the first capping layer and the second capping layer may each independently include one of compound HT28 to compound HT33, one of compound CP1 to compound CP6, β-NPB, or any combination thereof:

[0442]

[0443] electronic devices

[0444] Light-emitting devices can be included in various electronic devices. In this embodiment, the electronic device including the light-emitting device can be a light-emitting device or an authentication device.

[0445] In addition to the light-emitting device, the electronic device (e.g., the light-emitting device) may further include i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and / or color conversion layer may be disposed in at least one direction of propagation of light emitted from the light-emitting device. For example, the light emitted from the light-emitting device may be blue light or white light. The light-emitting device can be understood by referring to the description provided herein. In embodiments, the color conversion layer may include quantum dots. Quantum dots may be, for example, the quantum dots described herein.

[0446] The electronic device may include a first substrate. The first substrate may include a plurality of sub-pixel regions, the color filter may include a plurality of color filter regions corresponding to the plurality of sub-pixel regions, and the color conversion layer may include a plurality of color conversion regions corresponding to the plurality of sub-pixel regions.

[0447] A pixel-defining film can be located between multiple sub-pixel regions to define each sub-pixel region.

[0448] The color filter may further include a plurality of color filter regions and a light-blocking pattern between the plurality of color filter regions, and the color conversion layer may further include a plurality of color conversion regions and a light-blocking pattern between the plurality of color conversion regions.

[0449] Multiple color filter regions (or multiple color conversion regions) may include: a first region emitting a first color light; a second region emitting a second color light; and / or a third region emitting a third color light, wherein the first color light, the second color light, and / or the third color light may have different maximum emission wavelengths. In an embodiment, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. In an embodiment, each of the multiple color filter regions (or multiple color conversion regions) may include a quantum dot. In an embodiment, the first region may include a red quantum dot, the second region may include a green quantum dot, and the third region may not include a quantum dot. Quantum dots can be understood by referring to the description of quantum dots provided herein. The first region, the second region, and / or the third region may each further include an emitter.

[0450] In one embodiment, the light-emitting device can emit first light, a first region can absorb the first light to emit a first first color light, a second region can absorb the first light to emit a second first color light, and a third region can absorb the first light to emit a third first color light. In another embodiment, the first, second, and third first color lights can each have a different maximum emission wavelength. In yet another embodiment, the first light can be blue light, the first first color light can be red light, the second first color light can be green light, and the third first color light can be blue light.

[0451] In addition to the light-emitting device, the electronic device may further include a thin-film transistor. The thin-film transistor may include a source electrode, a drain electrode, and an active layer, wherein one of the source electrode and the drain electrode may be electrically connected to one of the first electrode and the second electrode of the light-emitting device.

[0452] Thin-film transistors may further include a gate electrode, a gate insulating film, and the like.

[0453] The active layer may include crystalline silicon, amorphous silicon, organic semiconductors, and oxide semiconductors.

[0454] The electronic device may further include an encapsulation unit for sealing the light-emitting device. The encapsulation unit may be located between the color filter and / or color conversion layer and the light-emitting device. The encapsulation unit allows light to pass from the light-emitting device to the outside while preventing air and moisture from penetrating into the light-emitting device. The encapsulation unit may be a sealing substrate comprising a transparent glass or plastic substrate. The encapsulation unit may be a thin-film encapsulation layer comprising at least one of an organic layer and an inorganic layer. When the encapsulation unit is a thin-film encapsulation layer, the electronic device may be flexible.

[0455] In addition to color filters and / or color conversion layers, various functional layers may be disposed on the package unit, depending on the purpose of the electronic device. Examples of functional layers may include a touchscreen layer, a polarizing layer, or a similar layer. The touchscreen layer may be a resistive touchscreen layer, a capacitive touchscreen layer, or an infrared touchscreen layer. The authentication device may be, for example, a biometric authentication device that identifies an individual based on biometric information (e.g., fingertip, pupil, or the like).

[0456] In addition to the light-emitting devices described above, the authentication device may further include a bio-information collection unit.

[0457] Electronic devices can be applied to the following devices: various displays, light sources, illuminators, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, electronic game consoles, medical devices (e.g., electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram recorders, ultrasound diagnostic devices, endoscopic display devices), fish detectors, various measuring devices, meters (e.g., meters for automobiles, airplanes, and ships), and projectors.

[0458] Figure 4 and Figure 5 Description

[0459] Figure 4 This is a schematic cross-sectional view of a light-emitting device according to an embodiment.

[0460] Figure 4 The light-emitting device may include a substrate 100, a thin-film transistor, a light-emitting device, and a packaging unit 300 for sealing the light-emitting device.

[0461] The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be on the substrate 100. The buffer layer 210 prevents the penetration of impurities through the substrate 100 and provides a flat surface on the substrate 100.

[0462] The thin-film transistor may be on the buffer layer 210. The thin-film transistor may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.

[0463] The active layer 220 may include inorganic semiconductors, organic semiconductors, or oxide semiconductors such as silicon or polysilicon, and includes a source region, a drain region, and a channel region.

[0464] A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be on the active layer 220, and the gate electrode 240 may be on the gate insulating film 230.

[0465] Interlayer insulating film 250 may be on gate electrode 240. Interlayer insulating film 250 may be between gate electrode 240 and source electrode 260 and between gate electrode 240 and drain electrode 270 to provide insulation therebetween.

[0466] The source electrode 260 and the drain electrode 270 may be on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source region and the drain region of the active layer 220, and the source electrode 260 and the drain electrode 270 may be adjacent to the exposed source region and the exposed drain region of the active layer 220.

[0467] In one embodiment, the thin-film transistor may be electrically connected to a light-emitting device to drive the light-emitting device, and may be protected by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or a combination thereof. The light-emitting device may be located on the passivation layer 280. The light-emitting device may include a first electrode 110, an intermediate layer 130, and a second electrode 150.

[0468] The first electrode 110 may be on the passivation layer 280. The passivation layer 280 may not completely cover the drain electrode 270 and may expose a specific area of ​​the drain electrode 270, and the first electrode 110 may be configured to connect to the exposed area of ​​the drain electrode 270.

[0469] A pixel defining film 290 may be on the first electrode 110. The pixel defining film 290 may expose a specific area of ​​the first electrode 110, and an intermediate layer 130 may be formed in the exposed area. The pixel defining film 290 may be a polyimide or polyacrylamide organic film. Although in Figure 4 Although not shown, some of the higher layers of the intermediate layer 130 may extend to the top of the pixel-defining film 290 and may therefore be configured as common layers.

[0470] The second electrode 150 may be on the intermediate layer 130, and a capping layer 170 may additionally be formed on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.

[0471] The encapsulation unit 300 may be on the cover layer 170. The encapsulation unit 300 may be on the light-emitting device to protect it from moisture or oxygen. The encapsulation unit 300 may include: an inorganic film, including silicon nitride (SiN). x ), silicon oxide (SiO) x Indium tin oxide, indium zinc oxide, or any combination thereof; organic membranes, including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resins (e.g., polymethyl methacrylate, polyacrylic acid and the like), epoxy resins (e.g., aliphatic glycidyl ether (AGE) and the like) or any combination thereof; or combinations of inorganic and organic membranes.

[0472] Figure 5 This is a schematic cross-sectional view of another light-emitting device according to an embodiment.

[0473] In addition to the light-shielding pattern 500 and the functional area 400 being located on the packaging unit 300, Figure 5 The light-emitting device shown can be used with Figure 4 The light-emitting devices shown are essentially the same. Functional region 400 can be i) a color filter region, ii) a color conversion region, or iii) a combination of a color filter region and a color conversion region. In embodiments, included in the light-emitting device... Figure 5 The light-emitting device shown can be a series light-emitting device.

[0474] Manufacturing method

[0475] The layers constituting the hole transport region, the emission layer, and the electron transport region can be formed in specific regions using one or more suitable methods, such as vacuum deposition, spin coating, casting, Langmuir-Blodget (LB) deposition, inkjet printing, laser printing, and laser-induced thermal imaging.

[0476] When layers constituting the hole transport region, the emitter layer, and the electron transport region are independently formed by vacuum deposition, the deposition temperature can be in the range of about 100°C to about 500°C, depending on the materials included in each layer and the structure of each layer. -8 To about 10 -3 The vacuum level in the Torr range is approximately 0.01 angstroms per second. to approximately Vacuum deposition is performed within the range of deposition rates.

[0477] General definition of terminology

[0478] The term "C3-C" as used in this article 60 A "carbocyclic group" refers to a cyclic group consisting only of carbon atoms and having 3 to 60 carbon atoms. The term "C1-C" as used herein... 60 A "heterocyclic group" refers to a cyclic group that has 1 to 60 carbon atoms in addition to heteroatoms other than carbon atoms. Two types of groups (C3-C4) are also mentioned. 60 Carbocyclic groups and C1-C 60 Heterocyclic groups (including aromatic and non-aromatic cyclic groups) are cyclic groups. C3-C 60 Carbocyclic groups and C1-C 60 Heterocyclic groups can each be a monocyclic group consisting of one ring or a polycyclic group in which at least two rings are fused. For example, C1-C 60 The number of cyclic atoms in a heterocyclic group can range from 3 to 61.

[0479] The term "cyclic group" as used in this article may include C3-C 60 Carbocyclic groups and C1-C 60 Heterocyclic groups.

[0480] The term "π-electron-rich C3-C" 60 "Cyclic group" refers to a cyclic group having 3 to 60 carbon atoms and excluding *-N=*' as the cyclic moiety. For example, the term "nitrogen-containing C1-C lacking π electrons" is used herein. 60 "Cyclic groups" refer to heterocyclic groups having 1 to 60 carbon atoms and *-N=*' as the cyclic part.

[0481] In the implementation,

[0482] C3-C 60 The carbocyclic group may be: i) a T1 group or ii) a group in which at least two T1 groups are fused together (e.g., cyclopentadienyl, adamantyl, norbornel, phenyl, pentadienyl, naphthyl, azuleyl, indaryl, acenaphthenic, phenanthreneyl, phenanthreneyl, anthraceneyl, fluoranyl, benzo[phenanthrene], pyrene, etc.). (e.g., peryl, pentaphenyl, heptaphenyl, naphthonaphthyl, fumaryl, hexaphenyl, pentaphenyl, rutinyl, hexabenzophenyl, ovoidyl, indene, fluorenyl, spiro-bisfluorenyl, benzo[fluorenyl], indene-butyryl or indene-anthrayl)

[0483] In the implementation method, C1-C 60The heterocyclic group may be: i) a T2 group, ii) a group in which at least two T2 groups are fused, or iii) a group in which at least one T2 group and at least one T1 group are fused (e.g., pyrrole, thiophene, furanyl, indole, benzoindole, naphthoindole, isoindole, benzoisoindole, benzosiloxanepentadienyl, benzothiophene, benzofuranyl, carbazole, dibenzosiloxanepentadienyl, dibenzothiophene, dibenzofuranyl, indocarbazole, indolecarbazole, benzofuranocarbazole, benzothiophenecarbazole, benzosiloxanepentadienocarbazole, benzoindocarbazole, benzocarbazole, benzonaphthofuranyl, benzonaphthothiophene, benzonaphthosiloxanepentadienyl, benzofuranodibenzofuranyl, benzofurano Dibenzothiophene, benzothiophene-dibenzothiophene, pyrazolyl, imidazole, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiazolyl, benzopyrazolyl, benzimidazolyl, benzooxazolyl, benziisooxazolyl, benzothiazolyl, benzoisothiazolyl, pyridyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinoline (including benzo[a]isoquinolinyl, quinoxalinyl, benzo[a]quinoxalinyl, quinazolinyl, benzo[a]quinazolinyl, phenanthrene, cinolinyl, phthalazinyl, naphthidyl, imidazo[a]pyridinyl, imidazo[a]pyrimidinyl, imidazo[a]triazinyl, imidazo[a]pyrazinyl, imidazo[a]pyridazinyl, azacarbazolyl, azafluorenyl, azadibenzo[a]silazocpentadienyl, azadibenzo[a]thiopheneyl, azadibenzo[a]furanyl and analogues).

[0484] In the implementation method, C3-C rich in π electrons 60 The cyclic group may be: i) a T1 group, ii) a fused group in which at least two T1 groups are fused, iii) a T3 group, v) a fused group in which at least two T3 groups are fused, or v) a fused group in which at least one T3 group and at least one T1 group are fused (e.g., C3-C). 60 Carbocyclic groups, pyrrole, thiophene, furanyl, indole, benzoindole, naphthoindole, isoindole, benzoisoindole, naphthoisoindole, benzosiloxanediyl, benzothiophene, benzofuranyl, carbazole, dibenzosiloxanediyl, dibenzothiophene, dibenzofuranyl, indolecarbazole, indolecarbazole, benzofuranoxanecarbazole, benzothiophenecarbazole, benzosiloxanediylcarbazole, benzoindolecarbazole, benzocarbazole, benzonaphthofuranyl, benzonaphthothiophene, benzonaphthosiloxanediyl, benzofuranoxanedibenzofuranyl, benzofuranoxanedibenzothiophene, benzothiophenedibenzothiophene and analogues).

[0485] In the implementation method, nitrogen-containing C1-C lacking π electrons 60The cyclic group may be: i) a T4 group; ii) a group in which at least two T4 groups are fused; iii) a fused cyclic group in which at least one T4 group and at least one T1 group are fused; iv) a group in which at least one T4 group and at least one T3 group are fused together; or v) a group in which at least one T4 group, at least one T1 group, and at least one T3 group are fused together (e.g., pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiazolyl, benzopyrazolyl, benzimidazolyl, benzyl... Benzoxazolyl, benzoisoxazolyl, benzothiazolyl, benzoisothiazolyl, pyridyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrene, terpineyl, phthalazinyl, naphthidyl, imidazopyridine, imidazopyrimidyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzosilylopadienyl, azadibenzothiophene, azadibenzofuranyl and analogues).

[0486] In embodiments, the T1 group may be cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, cycloheptenyl, adamantyl, norbornane (or bicyclo[2.2.1]heptane) group, norbornenyl, bicyclo[1.1.1]pentane, bicyclo[2.1.1]pentane, bicyclo[2.2.2]octane, or phenyl.

[0487] The T2 group can be furanyl, thiophene, 1H-pyrrole, silycyclopentadienyl, borocyclopentadienyl, 2H-pyrrole, 3H-pyrrole, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiazolyl, aziridinyl, aziboroxadienyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, or tetraazinyl.

[0488] The T3 group can be furanyl, thiophene, 1H-pyrrole, siloxycyclopentadienyl, or borocyclopentadienyl, and

[0489] The T4 group can be 2H-pyrrole, 3H-pyrrole, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiazolyl, azasilole, azaborole, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, or tetraazinyl.

[0490] The terms "cyclic group" and "C3-C" used in this article 60"Carbocyclic group", "C1-C" 60 Heterocyclic groups, C3-C rich in π electrons 60 "Cyclic groups" or "nitrogen-containing C1-C groups lacking π electrons" 60 "Cyclic group" can be a group fused with any suitable cyclic group, monovalent group, or polyvalent group (e.g., divalent group, trivalent group, tetravalent group, or similar group) according to the structure of the formula used in the application term. For example, "phenyl" can be a benzo[a] group, phenyl, phenylene, or similar group, and this will be understood by those skilled in the art based on the structure of the formula including "phenyl".

[0491] Monovalent C3-C 60 Carbocyclic groups and monovalent C1-C 60 Examples of heterocyclic groups may include C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups. Divalent C3-C 60 Carbocyclic groups and divalent C1-C 60 Examples of heterocyclic groups may include C3-C 10 Cycloalkylene, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkylene, C1-C 10 Heterocyclic alkenyl, C6-C 60 aryl, C1-C 60 Hypoaryl groups, divalent non-aromatic fused polycyclic groups, and divalent non-aromatic fused heterocyclic groups.

[0492] The term "C1-C" as used in this article 60 "Alkyl" refers to a monovalent group of a straight-chain or branched aliphatic hydrocarbon having 1 to 60 carbon atoms, examples of which include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl, and tert-decyl. The term "C1-C" as used herein... 60 "alkylene" refers to a compound with C1-C2 atoms. 60 Divalent groups with the same structure as alkyl groups.

[0493] The term "C2-C" as used in this article 60"Alkenyl" refers to a group with a C2-C... 60 A hydrocarbon group having at least one carbon-carbon double bond in the middle or at the end of an alkyl group. Examples include vinyl, propenyl, and butenyl. The term "C2-C" as used herein... 60 "Alkenyl sub-chain" refers to a chain with a structure similar to C2-C2. 60 Divalent groups with the same structure as alkenyl groups.

[0494] The term "C2-C" as used in this article 60 "Alkyne group" refers to a group with a C2-C... 60 A monovalent hydrocarbon group consisting of at least one carbon-carbon triple bond in the middle or at the end of an alkyl group. Examples include ethynyl and propynyl. The term "C2-C" as used herein... 60 "Immyneyl" refers to a group that has a similar structure to C2-C2. 60 Divalent groups with the same structure as alkynyl groups.

[0495] The term "C1-C" as used in this article 60 "Alkoxy" refers to the compound formed by -OA 101 The monovalent group represents (where A) 101 For C1-C 60 Alkyl groups. Examples include methoxy, ethoxy, and isopropoxy groups.

[0496] The term "C1-C" as used in this article 60 "Alkylthio" refers to the group consisting of -SA 104 The monovalent group represents (where A) 104 For C1-C 60 Alkyl groups, and examples of them include methylthio, ethylthio, and isopropylthio.

[0497] The term "C3-C" as used in this article 10 "Cycloalkyl" refers to a monocyclic saturated hydrocarbon group comprising 3 to 10 carbon atoms. The term "C3-C" as used herein... 10 Examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, or bicyclo[2.2.1]octyl. The term "C3-C" as used herein... 10 "Cycloalkylene" refers to a compound with C3-C66 atoms. 10 Divalent groups with the same structure as cycloalkyl groups.

[0498] The term "C1-C" as used in this article 10"Heterocyclic alkyl" refers to a monovalent cyclic group having 1 to 10 carbon atoms, comprising at least one heteroatom other than a carbon atom as a cyclic atom. Examples include 1,2,3,4-oxatriazolyl, tetrahydrofuranyl, and tetrahydrothiophenyl. The term "C1-C" as used herein... 10 "Heterocyclic alkyl" refers to a compound with C1-C2 atoms. 10 Divalent groups with the same structure as heterocyclic alkyl groups.

[0499] The term "C3-C" as used in this article 10 "Cycloalkenyl" refers to a monovalent cyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring, and is not aromatic. Examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl. The term "C3-C" as used herein... 10 "Biopylidene alkenyl" refers to a group that has a C3-C... 10 A divalent group with the same structure as a cycloalkenyl group.

[0500] The term "C1-C" as used in this article 10 "Heterocyclic alkenyl" refers to a monovalent cyclic group comprising at least one heteroatom other than a carbon atom as a cyclic atom, 1 to 10 carbon atoms, and at least one double bond in its ring. C1-C 10 Examples of heterocyclic alkenyl groups include 4,5-dihydro-1,2,3,4-oxarizolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothiophenyl. The term "C1-C" as used herein... 10 "Heterocyclic alkyl" refers to a compound with C1-C2 atoms. 10 Divalent groups with the same structure as heterocyclic alkyl groups.

[0501] The term "C6-C" as used in this article 60 "Aryl" refers to a monovalent group in a carbocyclic aromatic system having 6 to 60 carbon atoms. The term "C6-C" is used herein. 60 "Arylene" refers to a divalent group that has a carbocyclic aromatic system with 6 to 60 carbon atoms. (C6-C) 60 Examples of aryl groups include phenyl, pentalenyl, naphthyl, azulel, indaryl, acenaphthel, phenalenyl, phenanthyl, anthracene, fluoranthracene, benzo[a]phenanthrene, pyrene, etc. alkyl, peryl, pentaphenyl, heptaphenyl, tetraphenyl, ramyl, hexaphenyl, pentaphenyl, rubidyl, phenyl, and curcumyl. When C6-C 60 Aryl and C6-C 60 When each of the aryl groups independently comprises two or more rings, the individual rings can be fused.

[0502] The term "C1-C" as used in this article60 "Heteroaryl" refers to a monovalent group in a heterocyclic aromatic system having at least one heteroatom other than a carbon atom as a cyclic atom and 1 to 60 carbon atoms. The term "C1-C" as used herein... 60 "Hypo-heteroaryl" refers to a divalent group in a heterocyclic aromatic system that further includes at least one heteroatom other than a carbon atom as a cyclic atom and 1 to 60 carbon atoms. C1-C 60 Examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, benzo[a]quinolinyl, isoquinolinyl, benzo[a]isoquinolinyl, quinoxalinyl, benzo[a]quinoxalinyl, quinazolinyl, benzo[a]quinazolinyl, cyclolinyl, phenanthrolinel, phthalazinyl, and naphthidyl. When C1-C 60 heteroaryl and C1-C 60 When each heteroaryl group independently comprises two or more rings, the individual rings can be fused.

[0503] As used herein, the term "monovalent nonaromatic fused polycyclic group" refers to a monovalent group having two or more fused rings and only carbon atoms as cyclic atoms (e.g., 8 to 60 carbon atoms), wherein the molecular structure is nonaromatic when considered as a whole. Examples of monovalent nonaromatic fused polycyclic groups include indenyl, fluorenyl, spiro-bisfluorenyl, benzo[a]fluorenyl, indeno[a]phenanthryl, and indeno[a]anthrayl. As used herein, the term "divalent nonaromatic fused polycyclic group" refers to a divalent group having substantially the same structure as a monovalent nonaromatic fused polycyclic group.

[0504] The term “monovalent non-aromatic fused heterocyclic group” as used herein refers to a monovalent group having two or more fused rings and at least one heteroatom other than carbon atoms (e.g., 1 to 60 carbon atoms) as a cyclic atom, wherein the molecular structure is non-aromatic when considered as a whole. Examples of monovalent non-aromatic fused heterocyclic groups include: pyrrole, thiophene, furanyl, indole, benzoindole, naphthoindole, isoindole, benzoisoindole, naphthoisoindole, benzosiloxanediyl, benzothiophene, benzofuranyl, carbazole, dibenzosiloxanediyl, dibenzothiophene, dibenzofuranyl, azacarbazole, azafluorenyl, azabenzosiloxanediyl, azadibenzothiophene, azadibenzofuranyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiazolyl ... Diazole, benzopyrazolyl, benzoimidazolyl, benzooxazolyl, benzothiazolyl, benzooxadiazole, benzothiadiazole, imidazopyridyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, indolecarbazole, indolocarbazole, benzofuranocarbazole, benzothiophenocarbazole, benzosilicyclopentadienocarbazole, benzoindolocarbazole, benzocarbazole, benzonaphthiofuranyl, benzonaphthiophenyl, benzonaphthiophenenyl, benzofuranodibenzofuranyl, benzofuranodibenzothiophenyl, and benzothiophenebenzothiophenyl. The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having substantially the same structure as a monovalent non-aromatic fused heteropolycyclic group.

[0505] The term "C6-C" as used in this article 60 "Aryloxy group" is composed of -OA 102 Indicates (where A) 102 For C6-C 60 Aryl). The term "C6-C" as used in this article 60 "Arylthio" is composed of -SA 103 Indicates (where A) 103 For C6-C 60 Aryl).

[0506] The term "C1-C" as used in this article 60 "Heteroaryloxy" refers to -OA 105 (where A) 105 For C1-C 60 (Heteroaryl), and the term "C1-C" as used herein 60 "Heteroarylsulfur" indicator - SA 106 (where A) 106 For C1-C 60 (Miscellaneous aromatics).

[0507] The term "R" as used in this article 10a "Can be:

[0508] Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl, cyano, or nitro;

[0509] C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 alkynyl group, C1-C 60 alkylthio or C1-C 60 Alkoxy groups, which are individually unsubstituted or substituted with the following groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, -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 -P(=O)(Q) 11 (Q) 12 ), or any combination thereof;

[0510] C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 aryloxy group, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols or C6-C 60 Aryl thiols, each independently unsubstituted or substituted with the following groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C60 Heteroaryloxy, C1-C 60 heteroaryl thiols, -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 -P(=O)(Q) 21 (Q) 22 ), or any combination thereof; or

[0511] -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 ) or -P(=O)(Q 31 (Q) 32 ).

[0512] Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 And Q 31 To Q 33 Each can be independently represented as: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkoxy group; C1-C 60 Alkylthio group; C3-C 60 Carbocyclic groups, or C1-C 60 Heterocyclic groups, each of which is independently unsubstituted or substituted with the following groups: deuterium, -F, cyano, C1-C. 60 Alkyl, C1-C 60 Alkoxy, C1-C 60 Alkylthio, phenyl, biphenyl, or any combination thereof.

[0513] As used herein, the term "heteroatom" refers to any atom other than a carbon atom. Examples of heteroatoms may include O, S, N, P, Si, B, Ge, Se, or any combination thereof.

[0514] In this document, “Ph” represents phenyl, “Me” represents methyl, “Et” represents ethyl, and “ter-Bu” or “Bu” represents ethyl. t "" indicates tert-butyl, and "OMe" as used in this article indicates methoxy.

[0515] As used in this article, "biphenyl" refers to a phenyl group that has been substituted with at least one phenyl group. "Biphenyl" belongs to the group with a C6-C... 60 "Aryl" is "substituted phenyl" as a substituent.

[0516] The term "terphenyl" as used in this article refers to a phenyl group that is substituted by at least one phenyl group. "Terphenyl" belongs to the group that has a substituted C6-C phenyl group. 60 Aryl-substituted C6-C 60 "Aryl" is "substituted phenyl" as a substituent.

[0517] Unless otherwise defined, the symbols *, *', *” and *”' used in this document refer to the binding sites with adjacent atoms in the correspondence.

[0518] In the following, compounds and light-emitting devices according to one or more embodiments will be described in detail with reference to synthesis examples and examples. The term "using B instead of A" used in describing the synthesis examples means that the amount of B used is the same as the amount of A used in molar equivalents.

[0519] Example

[0520] 1. Synthesis of precursors of organic groups

[0521] Thiol-terminated block copolymers were prepared by a reversible addition-fragmentation chain transfer (RAFT) method. Chlorostyrene and trimethylamine monomers were distilled and purified, and dithioester structures were used as RAFT reagents.

[0522] Synthesis Example 1-1 (Synthesis of Precursor 1)

[0523] Precursor 1, m=10, n=10

[0524]

[0525] 5 g of 4-vinylbenzyl chloride monomer (0.033 mol), 0.0028 g of azobisisobutyronitrile (AIBN) (0.00017 mol), 0.5 g of dithioester RAFT reagent (0.0017 mol), and 10 g of benzene were mixed together. Gases were removed by a three-stage freeze-pump-thaw cycle. The resulting mixture was then stirred under vacuum at 70 °C for 2 hours, and the product was precipitated in acetone to give 2 g of intermediate 1-1 (Mn: 1,550 g / mol, PDI: 1.1).

[0526] dithioester RAFT reagent

[0527]

[0528] 2.1 g of N,N-diphenyl-4-vinylaniline (TPA) monomer (0.0078 mol), 0.001 g of AIBN (0.000065 mol), 1.0 g of intermediate 1-1 (0.00065 mol), and 10 g of benzene were mixed together. Gases were removed by a three-stage freeze-pump-thaw cycle. The resulting mixture was then stirred under vacuum at 70 °C for 2 hours, and the product was precipitated in acetone to obtain 1.2 g of intermediate 1-2 (Mn: 4,350 g / mol, PDI: 1.2).

[0529] Intermediate 1-2, 0.057 g of hexylamine (0.00056 mol), and 5 g of anhydrous (dry) tetrahydrofuran (THF) were mixed and stirred under a nitrogen atmosphere for 12 hours. The resulting product was then precipitated in methanol to obtain 1.2 g of intermediate 1-3.

[0530] 1.2 g of intermediate 1-3 (0.00028 mol), 0.022 g of sodium azide (0.00033 mol) and 5 g of dimethylformamide (DMF) were mixed, and the resulting mixture was stirred under a nitrogen atmosphere for 12 hours. The product was precipitated in methanol to obtain 1.2 g of precursor 1.

[0531] Synthesis Example 1-2 (Synthesis of Precursor 2)

[0532] Precursor 2, m = 10, n = 30

[0533]

[0534] 6.3 g of N,N-diphenyl-4-vinylaniline (TPA) monomer (0.0234 mol), 0.001 g of AIBN (0.000065 mol), 1.0 g of intermediate 1-1 (0.00065 mol), and 20 g of benzene were mixed together. Gases were removed by a three-stage freeze-pump-thaw cycle. The resulting mixture was then stirred under vacuum at 70 °C for 4 hours, and the product was precipitated in acetone to obtain 3.0 g of intermediate 2-2 (Mn: 10,000 g / mol, PDI: 1.2).

[0535] 3.0 g of intermediate 2-2 (0.0003 mol), 0.0606 g of hexylamine (0.0006 mol) and 10 g of anhydrous (dry) THF were mixed, and the resulting mixture was stirred under a nitrogen atmosphere for 12 hours. The product was precipitated in methanol to obtain 3.0 g of intermediate 2-3.

[0536] 3.0 g of intermediate 2-3 (0.0003 mol), 0.24 g of sodium azide (0.00036 mol) and 10 g of DMF were mixed, and the resulting mixture was stirred under a nitrogen atmosphere for 12 hours. The product was precipitated in methanol to obtain 3.0 g of precursor 2.

[0537] Synthesis Examples 1-3 (Synthesis of Precursor 3)

[0538] Precursor 3, m=10, n=60

[0539]

[0540] 12.6 g of N,N-diphenyl-4-vinylaniline (TPA) monomer (0.0468 mol), 0.001 g of AIBN (0.000065 mol), 1.0 g of intermediate 1-1 (0.00065 mol), and 30 g of benzene were mixed together. Gases were removed by a three-stage freeze-pump-thaw cycle. The resulting mixture was then stirred under vacuum at 70 °C for 4 hours, and the product was precipitated in acetone to obtain 5.0 g of intermediate 3-2 (Mn: 18,600 g / mol, PDI: 1.3).

[0541] 5.0 g of intermediate 3-2 (0.00027 mol), 0.06 g of hexylamine (0.00054 mol), and 10 g of anhydrous (dry) THF were mixed, and the resulting mixture was stirred under a nitrogen atmosphere for 12 hours. The resulting product was precipitated in methanol to obtain 5.0 g of intermediate 3-3.

[0542] 5.0 g of intermediate 3-3 (0.00027 mol), 0.3 g of sodium azide (0.00033 mol), and 15 g of DMF were mixed, and the resulting mixture was stirred under a nitrogen atmosphere for 12 hours. The product was precipitated in methanol to obtain 5.0 g of precursor 3.

[0543] Synthesis Examples 1-4 (Synthesis of Precursor 4)

[0544] Precursor 4, m=10, n=10

[0545]

[0546] 1.5 g of 9-vinylcarbazole monomer (0.0078 mol), 0.001 g of AIBN (0.000065 mol), 1.0 g of intermediate 1-1 (0.00065 mol), and 10 g of benzene were mixed together. Gases were removed by a three-stage freeze-pump-thaw cycle. The resulting mixture was then stirred under vacuum at 70 °C for 2 hours, and the product was precipitated in acetone to obtain 2.0 g of intermediate 4-2 (Mn: 3,520 g / mol, PDI: 1.2).

[0547] 2.0 g of intermediate 4-2 (0.00057 mol), 0.11 g of hexylamine (0.0011 mol), and 5 g of anhydrous (dry) THF were mixed, and the resulting mixture was stirred under a nitrogen atmosphere for 12 hours. The product was precipitated in methanol to obtain 1.8 g of intermediate 4-3.

[0548] 1.8 g of intermediate 4-3 (0.00051 mol), 0.04 g of sodium azide (0.00061 mol) and 5 g of DMF were mixed, and the resulting mixture was stirred under a nitrogen atmosphere for 12 hours. The product was precipitated in methanol to obtain 5.0 g of precursor 4.

[0549] Synthesis Examples 1-5 (Synthesis of Precursor 5)

[0550] Precursor 5, m=10, n=30

[0551]

[0552] 4.5 g of 9-vinylcarbazole monomer (0.0234 mol), 0.001 g of AIBN (0.000065 mol), 1.0 g of intermediate 1-1 (0.00065 mol), and 15 g of benzene were mixed together. Gases were removed by a three-stage freeze-pump-thaw cycle. The resulting mixture was then stirred under vacuum at 70 °C for 2 hours, and the product was precipitated in acetone to obtain 5.0 g of intermediate 5-2 (Mn: 7,400 g / mol, PDI: 1.2).

[0553] 5.0 g of intermediate 5-2 (0.00068 mol), 0.14 g of hexylamine (0.0014 mol), and 10 g of anhydrous (dry) THF were mixed, and the resulting mixture was stirred under a nitrogen atmosphere for 12 hours. The product was precipitated in methanol to obtain 4.6 g of intermediate 5-4.

[0554] 4.6 g of intermediate 5-4 (0.00062 mol), 0.05 g of sodium azide (0.00075 mol) and 15 g of DMF were mixed, and the resulting mixture was stirred under a nitrogen atmosphere for 12 hours. The product was precipitated in methanol to obtain 4.3 g of precursor 5.

[0555] Synthesis Examples 1-6 (Synthesis of Precursor 6)

[0556] Precursor 6, m=10, n=60

[0557]

[0558] 9.0 g of 9-vinylcarbazole monomer (0.047 mol), 0.001 g of AIBN (0.000065 mol), 1.0 g of intermediate 1-1 (0.00065 mol), and 20 g of benzene were mixed together. Gases were removed by a three-stage freeze-pump-thaw cycle. The resulting mixture was then stirred under vacuum at 70 °C for 9 hours, and the product was precipitated in acetone to obtain 9.2 g of intermediate 6-2 (Mn: 13,400 g / mol, PDI: 1.3).

[0559] 9.2 g of intermediate 6-2 (0.00068 mol), 0.14 g of hexylamine (0.0014 mol), and 10 g of anhydrous (dry) THF were mixed, and the resulting mixture was stirred under a nitrogen atmosphere for 12 hours. The product was precipitated in methanol to obtain 9.0 g of intermediate 6-3.

[0560] 9.0 g of intermediate 6-3 (0.00067 mol), 0.053 g of sodium azide (0.0008 mol) and 20 g of DMF were mixed, and the resulting mixture was stirred under a nitrogen atmosphere for 12 hours. The product was precipitated in methanol to obtain 8.7 g of precursor 6.

[0561] 2. Synthesis of materials containing quantum dots

[0562] Synthesis Example 2-1 (Synthesis of Compound 1)

[0563] Treatment 1: Synthesis of InP / ZnSeS

[0564] 1) Synthesis of InP nuclei

[0565] 0.2 g of indium acetate precursor (0.69 mmol), 0.38 g of zinc acetate (2.1 mmol), 1.2 mL of oleic acid (3.4 mmol), and 70 mL of 1-octadecene (ODE) were added to a 250 mL three-necked flask. After purging with nitrogen, the mixture was heated at 150 °C for 40 min, then cooled to room temperature. At room temperature, 2.3 mL of P(TMS)3 (0.91 mmol) was vigorously stirred and injected into a round flask. After the injection of P(TMS)3, the reaction temperature was increased from room temperature to 300 °C and maintained for 20 min. The resulting product was then cooled to 230 °C and held at this temperature for 40 min to form the InP core.

[0566] 2) Formation of ZnSeS shell

[0567] A ZnSeS gradient shell was formed on the synthesized InP-GaP core-shell. 0.275 g of Zn(OAc)₂ (1.5 mmol) was added to the reaction mixture, and the reaction was carried out at 230 °C for 1 h. 0.16 g of selenium was added to 2 mL of trioctylphosphine (TOP) solution, and the mixture was stirred until the Se-TOP solution became clear. Then, at 230 °C, 0.6 mL of Se-TOP solution (3 mmol) was added to a round flask over 15 seconds. Over 15 seconds, 0.72 mL of DDT (3 mmol) was added dropwise for injection. The reaction temperature was then rapidly increased to 300 °C, and the reaction was carried out for 20 min. The temperature was then lowered to 230 °C and the reaction was maintained at this temperature for 20 min or longer. Finally, the final reaction solution was cooled to room temperature and centrifuged and purified 2 to 3 times, alternating between methanol and acetone, to prepare InP / ZnSeS (620 nm) quantum dots.

[0568] Treatment 2: Synthesis of Material 1 containing quantum dots

[0569] 0.04 g of precursor 1 was dissolved in 4 mL of toluene, and 0.01 g of InP / ZnSeS was mixed together. The mixture was then stirred for 48 hours. The reaction product was precipitated in cold n-hexane and then dissolved in toluene for reprecipitation. This process was repeated three times. The carboxylic acid ligand was then removed to synthesize compound 1.

[0570] Synthetic Examples 2-1 to 2-6 (Synthesis of Compounds 2 to 6)

[0571] In Method 2, compounds 2 to 6 are synthesized in essentially the same manner as in Synthesis Example 2-1, except that precursors 2 to 6 are used in place of precursor 1.

[0572] 3. Preparation of cross-linked materials (films)

[0573] Example 1 (Preparation of Thin Film 1)

[0574] Process 1: Synthesis of Ink Composition 1

[0575] Compound 1 was dissolved in anisole solvent to a concentration of 1.5 wt% to prepare ink composition 1 (hereinafter referred to as "ink 1").

[0576] Nursing Care 2: Preparation of Thin Film 1

[0577] Ink 1 was spin-coated to form a monolayer film using a spin coater. The monolayer film was then dried and heat-treated at 180°C for 30 minutes using a hot plate. 50 μL of anisole solvent was coated onto the monolayer film, and after 30 minutes, the anisole solvent was absorbed using a wiper, followed by drying and heat treatment at 100°C for 1 minute using a hot plate.

[0578] A thin film with a thickness of 40 nanometers (nm) was prepared by baking a solvent-treated monolayer film in a heating furnace at 180°C for 30 minutes under a nitrogen atmosphere.

[0579] Examples 2 through 6 and Comparative Examples 1 through 3 (Thin Films 2 through 6 and Comparative Thin Films 1 through 3)

[0580] Thin films 2 to 6 and comparative films 1 to 3 were prepared in substantially the same manner as in Example 1, except that the compounds shown in Table 1 were used instead of compound 1 in treatment 1 and the inks shown in Table 1 were used instead of ink 1 in treatment 2.

[0581] Evaluation Example 1

[0582] To evaluate the properties of the films prepared in Examples 1 to 6 and Comparative Examples 1 to 3, the hole mobility of the films was measured using space charge confinement current (SCLC). The evaluation results of the films are shown in Table 1. The residual rates of the films in Table 1 were each measured using an exposure system in the following manner: by using 200 millijoules per square centimeter (mJ / cm²). 2 The film is exposed to ultraviolet light (365nm) to calculate the ultraviolet (UV) area of ​​the thin film and the UV area of ​​the monolayer film. The measured UV area of ​​the thin film is then divided by the measured UV area of ​​the monolayer film.

[0583] Table 1

[0584]

[0585] Organic groups of compounds 1 to 6, as well as compounds B and C

[0586]

[0587]

[0588] In compounds 1 through 6, as well as compounds B and C, * indicates the binding site with InP / ZnSeS.

[0589] In Table 1, it was found that the films of Examples 1 to 6 had significantly improved hole mobility compared with the films of Comparative Examples 1 to 3.

[0590] As is evident from the preceding description, cross-linked materials prepared by cross-linking compositions containing quantum dots have been found to have excellent or improved hole mobility and long or improved lifetime, and therefore, such cross-linked materials can be used to manufacture high-quality devices.

[0591] It should be understood that the embodiments described herein should be considered descriptive only and not for limiting purposes. Descriptions of features or aspects within each embodiment should generally be considered applicable to other similar features or aspects in other embodiments. While one or more embodiments have been described with reference to the accompanying drawings, it will be understood by those skilled in the art that various changes in form and detail may be made without departing from the spirit and scope of this detailed description as defined by the appended claims.

Claims

1. A material containing quantum dots, comprising: quantum dots; as well as Organic groups chemically bonded to the surface of the quantum dots. The organic groups include: azide groups and charge transport groups, and The charge-transfer group is not an unsubstituted phenyl group; The organic group mentioned therein is a group represented by Formula 1: Formula 1 Wherein, A1 and A2 are each independently a group represented by formula 2-1, formula 2-2a or formula 2-2b. Equation 2-1 Equation 2-2a Equation 2-2b In Equation 1, X1 is either O or S. Z1 to Z3 are each independent of: Single key; or Methylene, ethylene, n-propylene, isopropylene, n-butylene, sec-butylene, isobutylene, tert-butylene, n-pentylene, tert-pentylene, neopentylene, isopentylene, sec-pentylene, 3-pentylene, sec-isopentylene, n-hexylene, isohexylene, sec-hexylene, tert-hexylene, n-heptylene, isoheptylene, sec-heptylene, tert-heptylene, n-octylene, isooctylene, sec-octylene, tert-octylene, n-nonylene, n- Isononyl, sec-nonyl, tert-nonyl, n-decyl, isodeyl, sec-decyl, tert-decyl, phenylene, cyclopentadienyl, heptadienyl, naphthyl, azylene, adamantyl, acenaphthene, phenanthroline, anthracene, fluoranthroline, pyrene, benzophenanthrene, phenylene, tetraphenyl or perylene, each independently unsubstituted or substituted with the following groups: deuterium, hydroxyl, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 alkylthio, phenyl, biphenyl, or any combination thereof T1 is the end base. Wherein, at least one of the m A1 and n A2 is a group represented by formula 2-1. m and n are each independent integers between 50 and 500. * Indicates the binding site with the surface of the quantum dot. Among them, in equations 2-1, 2-2a, and 2-2b, Y1 and Y2 are each independently a single bond, or are either unsubstituted or replaced by at least one R. 10a Replacement C1-C 10 Alkylene L1 and L2 are each independently a single bond, unsubstituted, or bonded by at least one R. 10a Replacement C3-C 60 The carbocyclic group, or the unsubstituted group or the group with at least one R 10a Replacement C1-C 60 Heterocyclic groups, Among them, the C3-C 60 The carbocyclic group is C3 C 10 Cycloalkylene, C3 C 10 Cycloalkylene, C6 C 60 arylene or divalent non-aromatic fused polycyclic groups, wherein the C1-C 60 The heterocyclic group is C1 C 10 Heterocyclic alkyl, C1 C 10 Heterocyclic alkenyl, C1 C 60 Hypoaryl, or divalent non-aromatic fused heterocyclic groups, a1 and a2 are each independent integers from 1 to 3. R1 and R2 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 10 Alkyl, C2-C 10 Alkenyl, C2-C 10 alkynyl group, C1-C 10 Alkyl thio or C1-C 10 Alkoxy *' and *'' each indicate the binding site with the adjacent atom. R 10a is: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro; Methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl, tert-decyl, vinyl, propenyl, butenyl, ethynyl, propynyl, methylthio, ethylthio, isopropylthio, methoxy, ethoxy, or isopropoxy; or Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornelyl, i.e., bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, cyclopentadienyl, naphthyl, azuleyl, indoleyl, acenaphthel, phenanthrenyl, anthraceneyl, fluoranyl, benzo[2.2.2]phenanthryl, pyreneyl, pyrimidyl, peryl, indyl, fluorenyl, benzo[2.2.2]fluorenyl, 1,2,3,4-oxatriazolyl, 4,5-dihydro-1,2,3,4-oxatriazolyl, pyridyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, benzo[2.2.3]quinolinyl, isoquinolinyl, benzo[2.2.3]isoquinolinyl, phenanthroline, indoleyl, benzo[2.2.3]indoleyl, isoindoleyl, benzo[2.2.3] Isonidolyl, benzo[silicyclopentadienyl], benzo[thiophene], benzo[furanyl], carbazole, dibenzo[silicyclopentadienyl], dibenzo[thiophene], dibenzo[furanyl], azacarbazole, azafluorenyl, azadibenzo[silicyclopentadienyl], azadibenzo[thiophene], azadibenzo[furanyl], pyrazolyl, imidazolyl, triazolyl, tetrazolyl, benzopyrazolyl, benzo[imidazolyl], benzo[oxazolyl], benzo[thiazolyl], benzo[oxadiazolyl], benzo[thiazolyl], imidazo[pyridyl], imidazo[pyrimidinyl], indo[carbazole], benzo[furan[carbazole], benzo[thiaphen[carbazole], benzo[silicyclopentadien[carbazole], benzo[carbazole], phenoxy, cyclopentadienoxy Heptathenyloxy, naphthoxy, azuthoxy, indoleoxy, acenaphthoxy, phenanthoxy, phenanthroxy, anthrathoxy, fluoranthoxy, pyreneoxy, benzophenanthroxy, thyloxy, tetraphenyloxy, peryloxy, phenylthio, cyclopentadienylthio, heptathenylthio, naphthio, azuthio, indoleoxy, acenaphthio, phenanthio, phenanthrenethio, anthrathio, fluoranthoxy, pyrenethio, benzophenanthrenethio, thyloxy, tetraphenylthio, perylthio, pyrroleoxy, thiopheneoxy, furanyloxy, indoleoxy, benzoindoleoxy, isoindoleoxy, benzoisoindoleoxy, benzosiloxanedieneoxy, benzothiopheneoxy, benzofuranyloxy, carbazoleoxy, dibenzosiloxanedieneoxy Dibenzothiophenoxy, dibenzofuranoxy, indole-carbazoleoxy, indole-carbazoleoxy, benzofuran-carbazoleoxy, benzothiophene-carbazoleoxy, benzosiloxane-carbazoleoxy, benzocarbazoleoxy, pyrrolethio, thiophenethio, furanthio, indolethio, benzoindolethio, isoindolethio, benzoisoindolethio, benzosiloxanethio, benzothiophenethio, benzofuranthio, carbazolethio, dibenzosiloxanethio, dibenzothiophenethio, dibenzofuranthio, indole-carbazolethio, benzofuran-carbazolethio, benzothiophene-carbazolethio, benzosiloxane-carbazolethio or benzocarbazolethio. c34 is an integer from 0 to 4. c35 is an integer from 0 to 5. c38 is an integer from 0 to 8, and R 31 to R 33 each independently: Deuterium, hydroxyl or nitro; Methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl, tert-decyl, vinyl, propenyl, butenyl, ethynyl, propynyl, methylthio, ethylthio, isopropylthio, methoxy, ethoxy, or isopropoxy; or Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, i.e., bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, cyclopentadienyl, naphthyl, azuleyl, indoleyl, acenaphthel, phenanthrenyl, anthraceneyl, fluoranthrenyl, benzo[2.2.2]phenanthryl, pyrene, cyclo[2.2.2], perylene, indole, fluoreneyl, benzo[2.2.2]fluoreneyl, indoleyl, benzo[2.2.2]indoleyl, isoindoleyl, benzo[2.2.2]isoindoleyl, benzo[2.2.2]silanecyclopentadienyl, benzo[2.2.2]thiopheneyl, benzo[2.2.2]furanyl, carbazoleyl, diphenyl Benzylcyclopentadienyl, dibenzothiopheneyl, dibenzofuranyl, indole-carbazoleyl, indolo-carbazoleyl, benzofuran-carbazoleyl, benzothiophene-carbazoleyl, benzosilylopadien-carbazoleyl, benzo-carbazoleyl, phenoxy, cyclopentadienoxy, heptathenoxy, naphthoxy, azuthoxy, indole-salicylate, acenaphthoxy, phenanthoxy, phenanthroxy, anthrathoxy, fluoranthoxy, pyreneoxy, benzophenanthroxy, thoxy, tetraphenoxy, peryloxy, phenylthio, cyclopentadienylthio, heptathenylthio, naphthio, azuthio, indole-salicylate Phenothioyl, phenanthioyl, phenateranthioyl, anthracenethioyl, fluoranthracenethioyl, pyrenethioyl, benzo[phenanthrenethioyl], phenanthrenethioyl, tetraphenylthioyl, perylenethioyl, pyrrolooxy, thiophenoxy, furanoxy, indoleoxy, benzo[indoleoxy], isoindoleoxy, benzo[isoindoleoxy], benzo[siloxanedieneoxy], benzo[thiopheneoxy], benzo[furanoxy], carbazoleoxy, dibenzo[siloxanedieneoxy], dibenzo[thiopheneoxy], dibenzo[furanoxy], indole[carbazoleoxy], indole[carbazoleoxy], benzo[furan[carbazoleoxy], benzo[thiopheneoxy] Carbazole oxy, benzo[silicyclopentadien[carbazole oxy], benzo[carbazole oxy], pyrrole thio, thiophene thio, furan thio, indole thio, benzo[indole thio], isoindole thio, benzo[isoindole thio], benzo[silicyclopentadien[thio], benzo[thiophene thio], benzo[furan thio], carbazole thio, dibenzo[silicyclopentadien[thio], dibenzo[thiophene thio], dibenzo[furan thio], indole[carbazole thio], benzo[furan[carbazole thio], benzo[thiophene[carbazole thio], benzo[silicyclopentadien[carbazole thio] or benzo[carbazole thio].

2. The quantum dot-containing material of claim 1, wherein, The quantum dots include: Group II-VI semiconductor compounds; Group III-V semiconductor compounds; Group III-VI semiconductor compounds; Group I-III-VI semiconductor compounds; Group IV-VI semiconductor compounds; Group IV elements or compounds; or Any combination thereof.

3. The quantum dot containing material of claim 1, wherein, The charge-transporting group in the organic group is an electron-donating group or an electron-withdrawing group.

4. The quantum dot containing material of claim 1, wherein, The molar ratio of the azide group to the charge-transporting group in the organic group is in the range of 1:1 to 1:

10.

5. The quantum dot containing material of claim 1, wherein, The molar ratio of the organic group to the quantum dots in the quantum dot-containing material is in the range of 1:100 to 1:1,000.

6. The quantum dot containing material of claim 1, wherein, The average diameter of the quantum dot-containing material is in the range of 40 nanometers to 1,000 nanometers.

7. A method of making a material containing quantum dots, wherein, The quantum dot-containing material comprises quantum dots and organic groups chemically bonded to the surface of the quantum dots, wherein the organic groups include azide groups and charge-transporting groups that are not unsubstituted phenyl groups, and the method comprises: The quantum dots are chemically reacted with the precursor of the organic group to chemically bond the surface of the quantum dots to the organic group. The precursor of the organic group is represented by formula 1(1): Equation 1(1) Wherein, A1 and A2 are each independently a group represented by formula 2-1, formula 2-2a or formula 2-2b. Equation 2-1 Equation 2-2a Equation 2-2b In Equation 1(1), X1 is either O or S. Z1 to Z3 are each independent of: Single key; or Methylene, ethylene, n-propylene, isopropylene, n-butylene, sec-butylene, isobutylene, tert-butylene, n-pentylene, tert-pentylene, neopentylene, isopentylene, sec-pentylene, 3-pentylene, sec-isopentylene, n-hexylene, isohexylene, sec-hexylene, tert-hexylene, n-heptylene, isoheptylene, sec-heptylene, tert-heptylene, n-octylene, isooctylene, sec-octylene, tert-octylene, n-nonylene, n- Isononyl, sec-nonyl, tert-nonyl, n-decyl, isodeyl, sec-decyl, tert-decyl, phenylene, cyclopentadienyl, heptadienyl, naphthyl, azylene, adamantyl, acenaphthene, phenanthroline, anthracene, fluoranthroline, pyrene, benzophenanthrene, phenylene, tetraphenyl or perylene, each independently unsubstituted or substituted with the following groups: deuterium, hydroxyl, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 alkylthio, phenyl, biphenyl, or any combination thereof T1 is the end base. Wherein, at least one of the m A1 and n A2 is a group represented by formula 2-1. m and n are each independent integers between 50 and 500. Among them, in equations 2-1, 2-2a, and 2-2b, Y1 and Y2 are each independently a single bond, or are either unsubstituted or replaced by at least one R. 10a Replacement C1-C 10 Alkylene L1 and L2 are each independently a single bond, unsubstituted, or bonded by at least one R. 10a Replacement C3-C 60 The carbocyclic group, or the unsubstituted group or the group with at least one R 10a Replacement C1-C 60 Heterocyclic groups, Among them, the C3-C 60 The carbocyclic group is C3 C 10 Cycloalkylene, C3 C 10 Cycloalkylene, C6 C 60 arylene or divalent non-aromatic fused polycyclic groups, wherein the C1-C 60 The heterocyclic group is C1 C 10 Heterocyclic alkyl, C1 C 10 Heterocyclic alkenyl, C1 C 60 Hypoaryl, or divalent non-aromatic fused heterocyclic groups, a1 and a2 are each independent integers from 1 to 3. R1 and R2 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 10 Alkyl, C2-C 10 Alkenyl, C2-C 10 alkynyl group, C1-C 10 Alkyl thio or C1-C 10 Alkoxy *' and *" each indicate the binding site with the adjacent atom, and R 10a for: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro; Methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl, tert-decyl, vinyl, propenyl, butenyl, ethynyl, propynyl, methylthio, ethylthio, isopropylthio, methoxy, ethoxy, or isopropoxy; or Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornelyl, i.e., bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, cyclopentadienyl, naphthyl, azuleyl, indoleyl, acenaphthel, phenanthrenyl, anthraceneyl, fluoranyl, benzo[2.2.2]phenanthryl, pyreneyl, pyrimidyl, peryl, indyl, fluorenyl, benzo[2.2.2]fluorenyl, 1,2,3,4-oxatriazolyl, 4,5-dihydro-1,2,3,4-oxatriazolyl, pyridyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, benzo[2.2.3]quinolinyl, isoquinolinyl, benzo[2.2.3]isoquinolinyl, phenanthroline, indoleyl, benzo[2.2.3]indoleyl, isoindoleyl, benzo[2.2.3] Isonidolyl, benzo[silicyclopentadienyl], benzo[thiophene], benzo[furanyl], carbazole, dibenzo[silicyclopentadienyl], dibenzo[thiophene], dibenzo[furanyl], azacarbazole, azafluorenyl, azadibenzo[silicyclopentadienyl], azadibenzo[thiophene], azadibenzo[furanyl], pyrazolyl, imidazolyl, triazolyl, tetrazolyl, benzopyrazolyl, benzo[imidazolyl], benzo[oxazolyl], benzo[thiazolyl], benzo[oxadiazolyl], benzo[thiazolyl], imidazo[pyridyl], imidazo[pyrimidinyl], indo[carbazole], benzo[furan[carbazole], benzo[thiaphen[carbazole], benzo[silicyclopentadien[carbazole], benzo[carbazole], phenoxy, cyclopentadienoxy Heptathenyloxy, naphthoxy, azuthoxy, indoleoxy, acenaphthoxy, phenanthoxy, phenanthroxy, anthrathoxy, fluoranthoxy, pyreneoxy, benzophenanthroxy, thyloxy, tetraphenyloxy, peryloxy, phenylthio, cyclopentadienylthio, heptathenylthio, naphthio, azuthio, indoleoxy, acenaphthio, phenanthio, phenanthrenethio, anthrathio, fluoranthoxy, pyrenethio, benzophenanthrenethio, thyloxy, tetraphenylthio, perylthio, pyrroleoxy, thiopheneoxy, furanyloxy, indoleoxy, benzoindoleoxy, isoindoleoxy, benzoisoindoleoxy, benzosiloxanedieneoxy, benzothiopheneoxy, benzofuranyloxy, carbazoleoxy, dibenzosiloxanedieneoxy Dibenzothiophenoxy, dibenzofuranoxy, indole-carbazoleoxy, indole-carbazoleoxy, benzofuran-carbazoleoxy, benzothiophene-carbazoleoxy, benzosiloxane-carbazoleoxy, benzocarbazoleoxy, pyrrolethio, thiophenethio, furanthio, indolethio, benzoindolethio, isoindolethio, benzoisoindolethio, benzosiloxanethio, benzothiophenethio, benzofuranthio, carbazolethio, dibenzosiloxanethio, dibenzothiophenethio, dibenzofuranthio, indole-carbazolethio, benzofuran-carbazolethio, benzothiophene-carbazolethio, benzosiloxane-carbazolethio or benzocarbazolethio. c34 is an integer from 0 to 4. c35 is an integer from 0 to 5. c38 is an integer from 0 to 8, and R 31 to R 33 each independently: Deuterium, hydroxyl or nitro; Methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl, tert-decyl, vinyl, propenyl, butenyl, ethynyl, propynyl, methylthio, ethylthio, isopropylthio, methoxy, ethoxy, or isopropoxy; or Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, i.e., bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, cyclopentadienyl, naphthyl, azuleyl, indoleyl, acenaphthel, phenanthrenyl, anthraceneyl, fluoranthrenyl, benzo[2.2.2]phenanthryl, pyrene, cyclo[2.2.2], perylene, indole, fluoreneyl, benzo[2.2.2]fluoreneyl, indoleyl, benzo[2.2.2]indoleyl, isoindoleyl, benzo[2.2.2]isoindoleyl, benzo[2.2.2]silanecyclopentadienyl, benzo[2.2.2]thiopheneyl, benzo[2.2.2]furanyl, carbazoleyl, diphenyl Benzylcyclopentadienyl, dibenzothiopheneyl, dibenzofuranyl, indole-carbazoleyl, indolo-carbazoleyl, benzofuran-carbazoleyl, benzothiophene-carbazoleyl, benzosilylopadien-carbazoleyl, benzo-carbazoleyl, phenoxy, cyclopentadienoxy, heptathenoxy, naphthoxy, azuthoxy, indole-salicylate, acenaphthoxy, phenanthoxy, phenanthroxy, anthrathoxy, fluoranthoxy, pyreneoxy, benzophenanthroxy, thoxy, tetraphenoxy, peryloxy, phenylthio, cyclopentadienylthio, heptathenylthio, naphthio, azuthio, indole-salicylate Phenothioyl, phenanthioyl, phenateranthioyl, anthracenethioyl, fluoranthracenethioyl, pyrenethioyl, benzo[phenanthrenethioyl], phenanthrenethioyl, tetraphenylthioyl, perylenethioyl, pyrrolooxy, thiophenoxy, furanoxy, indoleoxy, benzo[indoleoxy], isoindoleoxy, benzo[isoindoleoxy], benzo[siloxanedieneoxy], benzo[thiopheneoxy], benzo[furanoxy], carbazoleoxy, dibenzo[siloxanedieneoxy], dibenzo[thiopheneoxy], dibenzo[furanoxy], indole[carbazoleoxy], indole[carbazoleoxy], benzo[furan[carbazoleoxy], benzo[thiopheneoxy] Carbazole oxy, benzo[silicyclopentadien[carbazole oxy], benzo[carbazole oxy], pyrrole thio, thiophene thio, furan thio, indole thio, benzo[indole thio], isoindole thio, benzo[isoindole thio], benzo[silicyclopentadien[thio], benzo[thiophene thio], benzo[furan thio], carbazole thio, dibenzo[silicyclopentadien[thio], dibenzo[thiophene thio], dibenzo[furan thio], indole[carbazole thio], benzo[furan[carbazole thio], benzo[thiophene[carbazole thio], benzo[silicyclopentadien[carbazole thio] or benzo[carbazole thio].

8. A crosslinked material comprising a crosslinked product of a quantum dot-containing material according to any one of claims 1 to 6.

9. The crosslinking material according to claim 8, wherein the crosslinking material comprises: Residues derived from the crosslinking reaction between the azide group and adjacent organic groups in the organic groups of the quantum dot-containing material.

10. The crosslinked material of claim 9, wherein, The azide group and the adjacent organic group exist in the same quantum dot-containing material, or the azide group and the adjacent organic group each exist in different quantum dot-containing materials.

11. The crosslinked material of claim 9, wherein, The residues include groups represented by Formula 4: Formula 4 In Equation 4, *', *" and *"' each indicate a binding site with an adjacent atom.

12. The crosslinked material of claim 8, wherein, The crosslinked material has the form of a membrane.

13. The crosslinked material of claim 12, wherein, The thickness of the membrane is in the range of 0.1 micrometers to 700 micrometers.

14. A method for preparing a crosslinked material, the method comprising: A quantum dot-containing material and solvent according to any one of claims 1 to 6 are provided on a substrate; as well as The quantum dot-containing material is cross-linked.

15. The method of claim 14, wherein, The quantum dot-containing material is cross-linked by exposure to ultraviolet light.

16. A light-emitting device, comprising: First electrode; The second electrode facing the first electrode; as well as An intermediate layer between the first electrode and the second electrode, including an emission layer. The light-emitting device includes the cross-linked material according to any one of claims 8 to 13.

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