Light emitting device
By employing an emission auxiliary layer without p-dopants in the light-emitting device and adjusting the HOMO energy level using a combination of compounds A and B, the problems of increased capacitance and hole resistance caused by p-dopants were solved, resulting in reduced driving voltage and extended lifespan.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2021-01-06
- Publication Date
- 2026-04-07
AI Technical Summary
The use of p-doped agents in existing light-emitting devices leads to increased capacitance and hole resistance, resulting in higher driving voltage and reduced lifespan.
By employing an emission auxiliary layer without p-doped material, and by using a combination of compounds A and B in the hole transport region, the HOMO energy levels of the compounds are adjusted to reduce the potential barrier and improve hole transport performance.
This achieves the maintenance or improvement of the performance of the light-emitting device, the reduction of the driving voltage, and the extension of the lifespan without the use of p-doped agents.
Smart Images

Figure CN113380955B_ABST
Abstract
Description
[0001] Cross-reference to related applications
[0002] This application claims priority and benefit to Korean Patent Application No. 10-2020-0029800, filed with the Korean Intellectual Property Office on March 10, 2020, the entire contents of which are incorporated herein by reference. Technical Field
[0003] One or more embodiments of this disclosure relate to a light-emitting device and an electronic device including said light-emitting device. Background Technology
[0004] Compared to other devices in the art, the light-emitting device is a self-emitting device with wide viewing angle, high contrast, short response time, and excellent characteristics in terms of brightness, driving voltage, and response speed.
[0005] In the light-emitting device, a first electrode is formed on a substrate, and a hole transport region, an emitter layer, an electron transport region, and a second electrode are sequentially formed on the first electrode. Holes supplied by the first electrode can move towards the emitter layer through the hole transport region, and electrons supplied by 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 light. Summary of the Invention
[0006] One or more embodiments include a device that does not contain a p-dopant in the emitter assist layer, but exhibits equal or better results compared to a device that contains a p-dopant in the emitter assist layer.
[0007] Additional aspects of the implementation scheme will be set forth in part in the following description and will be apparent in part from the description, or may be learned by practice of the implementation scheme presented in this disclosure.
[0008] According to one or more embodiments, the light-emitting device includes:
[0009] First electrode,
[0010] The second electrode facing the first electrode, and
[0011] An intermediate layer located between the first electrode and the second electrode and including an emission layer, wherein the intermediate layer comprises:
[0012] i) The hole transport region located between the first electrode and the emitter layer, and
[0013] ii) The electron transport region located between the emitter layer and the second electrode.
[0014] The hole transport zone includes two layers each comprising a compound Group A, a compound Group B, or any combination thereof,
[0015] The compound Group A includes one or two amine groups, and the amine groups include a fluorene moiety, a carbazole moiety, a dibenzofuran moiety, a dibenzothiophene moiety, a dibenzothianthene moiety, or any combination thereof, and
[0016] The compound Group B does not include an amine group, and includes a fluorene moiety, a carbazole moiety, a dibenzofuran moiety, a dibenzothiophene moiety, a dibenzothianthene moiety, or any combination thereof.
[0017] According to one or more embodiments, an electronic device includes:
[0018] a thin film transistor and the light emitting device, wherein the thin film transistor includes a source electrode, a drain electrode, an active layer, and a gate electrode, and the first electrode of the light emitting device is electrically connected to one selected from the source electrode and the drain electrode of the thin film transistor. BRIEF DESCRIPTION OF DRAWINGS
[0019] The above and other aspects and features of certain embodiments of the present disclosure will become more apparent from the following description, according to which Figure 1 is a schematic view of a light emitting device according to an embodiment. DETAILED DESCRIPTION
[0020] Reference will now be made in detail embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout. In this regard, the present embodiments can have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the following description is merely descriptive of the aspects of the presently described embodiments, and is not intended to limit the aspects of the present disclosure. 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 of a, b, and c, or variations thereof.
[0021] A p-dopant is a material for an emission-assisting layer, and is widely used because the p-dopant has properties of improving conductivity (e.g., electrical conductivity) and facilitating efficient hole injection from a hole transport layer.
[0022] However, such a p-dopant is expensive and causes an undesired increase in capacitance.
[0023] When the p-dopant is not used for the emission auxiliary layer, the barrier between the hole transport layer and the emission auxiliary layer increases, resulting in an increase in hole resistance, which increases the driving voltage of the light emitting device and reduces the service life, thereby deteriorating the performance of the light emitting device.
[0024] Accordingly, aspects of embodiments of the present disclosure provide a light emitting device, comprising:
[0025] a first electrode;
[0026] a second electrode facing the first electrode; and
[0027] an intermediate layer between the first electrode and the second electrode and comprising an emission layer, wherein the intermediate layer comprises:
[0028] i) a hole transport zone between the first electrode and the emission layer; and
[0029] ii) an electron transport zone between the emission layer and the second electrode,
[0030] the hole transport zone comprises two layers each comprising a compound Group A, a compound Group B, or any combination thereof,
[0031] the compound Group A comprises one or two amine groups, and the amine group comprises a fluorene moiety, a carbazole moiety, a dibenzofuran moiety, a dibenzothiophene moiety, a dibenzothianthene moiety, or any combination thereof, and
[0032] the compound Group B does not comprise an amine group, and comprises a fluorene moiety, a carbazole moiety, a dibenzofuran moiety, a dibenzothiophene moiety, a dibenzothianthene moiety, or any combination thereof.
[0033] The expression “the hole transport zone comprises two layers each comprising a compound Group A, a compound Group B, or any combination thereof” as used herein refers to a case where layer 1 comprises a compound Group A, a compound Group B, or any combination thereof, and layer 2 comprises a compound Group A, a compound Group B, or any combination thereof. For example, all the compounds contained in layer 1 and layer 2 can be different from each other. In some embodiments, for example, the respective compositions of layer 1 and layer 2 can be completely different, or there can be some overlap in the respective compositions. For example, layer 1 can contain one or more than one compound that is the same as one or more than one compound of layer 2, while the total composition of layer 1 and layer 2 is different from each other.
[0034] The expression "layer 1 comprises a compound group A, a compound group B, or any combination thereof" as used herein can mean "layer 1 comprises a compound belonging to the compound group A, the compound group B, or any combination thereof" or "layer 1 comprises two or more different compounds belonging to the compound group A, the compound group B, or any combination thereof". Expressions related to layer 2 have substantially the same meaning as described above.
[0035] In one embodiment, the first electrode can be an anode, the second electrode can be a cathode, and the hole transport zone can include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof.
[0036] In one or more embodiments, the first electrode can be an anode, the second electrode can be a cathode, and the electron transport zone can include a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0037] In one embodiment, the two layers included in the hole transport zone can be a hole transport layer and an emission auxiliary layer, respectively.
[0038] In the light-emitting device according to the embodiment, a material having a highest occupied molecular orbital (HOMO) energy level similar to that of the hole transport layer can be mixed in the emission auxiliary layer, thereby removing or reducing the energy barrier between the hole transport layer and the emission auxiliary layer. Thus, a structure not including a p-dopant in the emission auxiliary layer can exhibit equal or better performance even compared to a structure including a p-dopant in the emission auxiliary layer.
[0039] In one embodiment, the two layers included in the hole transport zone can be a hole transport layer and an emission auxiliary layer, respectively, wherein the hole transport layer can include a compound HTM selected from the compound group A, the compound group B, or any combination thereof, and
[0040] The emission auxiliary layer can include an auxiliary compound 1 and an auxiliary compound 2 selected from the compound group A, the compound group B, or any combination thereof.
[0041] Here, the compound HTM, the auxiliary compound 1, and the auxiliary compound 2 can be different from each other, and
[0042] The HOMO energy levels of the compound HTM, the auxiliary compound 1, and the auxiliary compound 2 can satisfy the following inequalities (1) and (2):
[0043] 0 eV < E HOMO_化合物HTM -E HOMO_辅助化合物2 ≤ 0.15 eV (1)
[0044] |E HOMO_辅助化合物1 -EHOMO_辅助化合物2 | < 0.20 eV (2).
[0045] In an embodiment, the emission assistance layer does not include a p-dopant. For example, the emission assistance layer can be free of (e.g., substantially free of or completely free of) a p-dopant.
[0046] Although the emission assistance layer does not include a p-dopant, the emission assistance layer includes a compound where the difference between the HOMO energy level of the compound and the HOMO energy level of the hole transport layer is 0.15 eV or lower, and thus, the difference in the HOMO energy level between two different compounds included in the emission assistance layer is 0.20 eV or lower, exhibiting equal or better performance compared to a structure where a p-dopant is included in the emission assistance layer.
[0047] In an embodiment, the compound HTM can include one of the following compounds:
[0048]
[0049]
[0050]
[0051]
[0052] In an embodiment, the auxiliary compound 1 and the auxiliary compound 2 can each include one of the following compounds:
[0053]
[0054]
[0055] In an embodiment, the weight ratio of the auxiliary compound 1 and the auxiliary compound 2 can be about 1:9 to about 9:1. For example, the weight ratio of the auxiliary compound 1 and the auxiliary compound 2 can be about 3:7 to about 7:3. For example, the weight ratio of the auxiliary compound 1 and the auxiliary compound 2 can be about 4:5 to about 5:4.
[0056] In an embodiment, the emission assistance layer can be in contact (e.g., physical contact) with the emission layer.
[0057] In an embodiment, the emission assistance layer can be in contact (e.g., physical contact) with the hole transport layer.
[0058] In an embodiment, the emission layer can include two or more hosts. For example, the emission layer can include two different hosts.
[0059] In an embodiment, the emissive layer can include a premixed host. The premixed host is introduced by using a single source prepared by mixing two or more hosts during a deposition process, and is distinguished from a host prepared using two or more sources in a co-deposition process.
[0060] In an embodiment, the hole transport zone can include a hole transport layer including a charge generating material, instead of a hole injection layer. For example, the hole transport zone of the light emitting device can include a hole transport layer including a charge generating material, an emission auxiliary layer including a charge generating material, an electron blocking layer including a charge generating material, or any combination thereof.
[0061] In an embodiment, the charge generating material can be a p-dopant.
[0062] In an embodiment, the p-dopant can include a quinone derivative, a metal oxide, a cyano group-containing compound, or any combination thereof.
[0063] In an embodiment, the quinone derivative can be TCNQ or F4-TCNQ:
[0064]
[0065] In an embodiment, the metal oxide can be tungsten oxide and / or molybdenum oxide.
[0066] In an embodiment, the cyano group-containing compound can be HAT-CN and / or from
[0067] a compound represented by Formula 221:
[0068]
[0069] Formula 221
[0070]
[0071] In Formula 221,
[0072] R 221 to R 223 may each independently be a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 heterocycloalkyl group, a substituted or unsubstituted C3-C 10 cycloalkenyl group, a substituted or unsubstituted C1-C 10 heterocycloalkenyl group, a substituted or unsubstituted C6-C 60 aryl group, a substituted or unsubstituted C1-C 60a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group.
[0073] R 221 to R 223 Each of at least one of R 20 may be independently substituted with a cyano group; -F; -Cl; -Br; -I; a C1-C 20 alkyl group; a C1-C 20 alkyl group; a C1-C 20 alkyl group; a C1-C 20 alkyl group; or any combination thereof. 10 cycloalkyl group, a C1-C 10 heterocycloalkyl group, a C3-C 10 cycloalkenyl group, a C1-C 10 heterocycloalkenyl group, a C6-C 60 aryl group, a C1-C 60 heteroaryl group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group.
[0074] Another aspect of embodiments of the present disclosure provides an electronic device including: a thin film transistor; and a light emitting device, wherein the thin film transistor includes a source electrode, a drain electrode, an active layer, and a gate electrode, and a first electrode of the light emitting device is electrically connected to one of the source electrode and the drain electrode of the thin film transistor.
[0075] The term "intermediate layer" as used herein refers to a single layer and / or all layers between the first electrode and the second electrode of the light emitting device. The material included in the "intermediate layer" can be an organic material, an inorganic material, or any combination thereof.
[0076] Figure 1 is a schematic cross-sectional view of a light emitting device 10 according to an embodiment. The light emitting device 10 includes a first electrode 110, an intermediate layer 150, and a second electrode 190.
[0077] Hereinafter, the structure of the light emitting device 10 according to an embodiment and a method of manufacturing the light emitting device 10 will be described with reference to the accompanying drawings.
[0078] The first electrode 110
[0079] In the drawings, a substrate can be additionally positioned below the first electrode 110 or above the second electrode 190. The substrate can be a glass substrate or a plastic substrate.
[0080] The first electrode 110 can be formed by, for example, depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, a material having a high work function that facilitates hole injection can be used as the material for forming the first electrode 110.
[0081] The first electrode 110 can be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. In one embodiment, when the first electrode 110 is a transmissive electrode, the material for forming the first electrode 110 can be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and any combination thereof, although embodiments of the present disclosure are not limited thereto. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the material for forming the first electrode 110 can be magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof, although embodiments of the present disclosure are not limited thereto.
[0082] The first electrode 110 can have a single-layer structure including (or consisting of) a single layer or a multi-layer structure including a plurality of layers. For example, the first electrode 110 can have a three-layer structure of ITO / Ag / ITO, although the structure of the first electrode 110 is not limited thereto.
[0083] The intermediate layer 150
[0084] The intermediate layer 150 can be located on the first electrode 110. The intermediate layer 150 can include an emission layer.
[0085] The intermediate layer 150 can further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 190.
[0086] In addition to various suitable organic materials, the intermediate layer 150 can further include a metal-containing compound (e.g., an organometallic compound), an inorganic material (e.g., a quantum dot), etc.
[0087] The hole transport region in the intermediate layer 150
[0088] The hole transport region can have i) a single-layer structure including (or consisting of) a single layer including (or consisting of) a single material, ii) a single-layer structure including (or consisting of) a single layer including (or consisting of) a plurality of different materials, or iii) a multi-layer structure including a plurality of layers including different materials.
[0089] The hole transport zone can include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof. As described above, the hole transport zone can include a hole transport layer including a charge generating material, instead of a hole injection layer.
[0090] For example, the hole transport zone can have a multi-layer structure including 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, in each of which the layers are sequentially stacked from the first electrode 110, but embodiments of the present disclosure are not limited thereto.
[0091] The hole transport zone can include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
[0092] Formula 201
[0093]
[0094] Formula 202
[0095]
[0096] In Formula 201 and Formula 202,
[0097] L 201 to L 204 may each independently be a substituted or unsubstituted C3-C 10 cycloalkylene group, a substituted or unsubstituted C1-C 10 heterocycloalkylene group, a substituted or unsubstituted C3-C 10 cycloalkenylene group, a substituted or unsubstituted C1-C 10 heterocycloalkenylene group, a substituted or unsubstituted C6-C 60 arylene group, a substituted or unsubstituted C1-C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic fused polycyclic group, or a substituted or unsubstituted divalent non-aromatic fused heteropolycyclic group,
[0098] L 205 may be *-O-*', *-S-*', *-N(Q 201 )-*', a substituted or unsubstituted C1-C 20 alkylene group, a substituted or unsubstituted C2-C 20 alkenylene group, a substituted or unsubstituted C3-C 10 cycloalkylene group, a substituted or unsubstituted C1-C 10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 arylene groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, or substituted or unsubstituted divalent nonaromatic fused heterocyclic groups,
[0099] xa1 to xa4 can each be 0, 1, 2, or 3 independently (e.g., 0, 1, or 2).
[0100] xa5 can be an integer from 1 to 10 (e.g., 1, 2, 3, or 4), and
[0101] R 201 To R 204 and Q 201 Each can be either substituted or unsubstituted C3-C independently. 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thioyl groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups.
[0102] For example, in equation 202, R 201 and R 202 They can optionally be linked to each other via single bonds, dimethyl-methylene groups, or diphenyl-methylene groups, and R 203 and R 204 They can be optionally linked together via single bonds, dimethyl-methylene groups, or diphenyl-methylene groups.
[0103] In one implementation, i) R in Equation 201 201 To R 203 At least one of them and R in equation 202 (ii) 201 To R 204 At least one of them can be independently unsubstituted or replaced by deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 20 Alkyl groups, C1-C 20at least one of an alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C1-C20alkyl group, a phenyl group substituted with a -F, a naphthyl group, a phenanthryl group, an indenyl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dimethylbenzofluorenyl group, a diphenylbenzofluorenyl group, an indenophenanthryl group, a dimethylindenophenanthryl group, a diphenylindenophenanthryl group, a pyridyl group, a pyrrolyl group, a thienyl group, a furanyl group, an indolyl group, a phenylindolyl group, a benzoindolyl group, a phenylbenzoindolyl group, an isoindolyl group, a phenylisoindolyl group, a benzoisoindolyl group, a phenylbenzoisoindolyl group, a benzothiophyl group, a benzofuranyl group, a carbazolyl group, a phenylcarbazolyl group, a biphenylcarbazolyl group, a dibenzothiophyl group, a dibenzofuranyl group, a fluorenyl group substituted with at least one of a carbazolyl group, a benzothiophyl group, a benzofuranyl group, a carbazolyl group, a dibenzothiophyl group, or a dibenzofuranyl group, but embodiments of the present disclosure are not limited thereto. 10 at least one of an alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C1-C20alkyl group, a phenyl group substituted with a -F, a naphthyl group, a phenanthryl group, an indenyl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dimethylbenzofluorenyl group, a diphenylbenzofluorenyl group, an indenophenanthryl group, a dimethylindenophenanthryl group, a diphenylindenophenanthryl group, a pyridyl group, a pyrrolyl group, a thienyl group, a furanyl group, an indolyl group, a phenylindolyl group, a benzoindolyl group, a phenylbenzoindolyl group, an isoindolyl group, a phenylisoindolyl group, a benzoisoindolyl group, a phenylbenzoisoindolyl group, a benzothiophyl group, a benzofuranyl group, a carbazolyl group, a phenylcarbazolyl group, a biphenylcarbazolyl group, a dibenzothiophyl group, a dibenzofuranyl group, a fluorenyl group substituted with at least one of a carbazolyl group, a benzothiophyl group, a benzofuranyl group, a carbazolyl group, a dibenzothiophyl group, or a dibenzofuranyl group, but embodiments of the present disclosure are not limited thereto.
[0104] In one embodiment, the compound represented by Formula 201 or Formula 202 can include at least one carbazolyl group.
[0105] In one or more embodiments, the compound represented by Formula 201 can not include a carbazolyl group.
[0106] In one embodiment, the hole transport zone can include at least one selected from 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 / camphor sulfonic acid (PANI / CSA), and polyaniline / poly(4-styrenesulfonate) (PANI / PSS):
[0107] In one embodiment, the hole transport zone can include at least one selected from 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 / camphor sulfonic acid (PANI / CSA), and polyaniline / poly(4-styrenesulfonate) (PANI / PSS):
[0108] The thickness of the hole transport region can be approximately to approximately For example, about to approximately When the hole transport region includes at least one selected from the hole injection layer and the hole transport layer, the thickness of the hole injection layer can be approximately to approximately For example, about to approximately Furthermore, the thickness of the hole transport layer can be approximately to approximately For example, about to approximately When the thicknesses of the hole transport region, hole injection layer, and hole transport layer are within these ranges, suitable or satisfactory hole transport characteristics can be obtained without a significant increase in driving voltage.
[0109] The launch assistance layer can be understood by referring to the description provided above.
[0110] An electron blocking layer can be used to prevent or reduce electron injection from electron transport regions. The electron blocking layer may contain materials as described above.
[0111] p-dopants
[0112] In addition to the materials described above, the hole transport region may further include charge-generating materials for improving conduction (e.g., electrical conductivity) properties. The charge-generating materials may be uniformly or non-uniformly dispersed in the hole transport region.
[0113] The charge-generating material can be, for example, a p-doped agent.
[0114] In one embodiment, the lowest unoccupied molecular orbital (LUMO) level of the p-dopant can be about -3.5 eV or less than -3.5 eV.
[0115] p-dopers can be understood by referring to the description provided above.
[0116] For example, p-dopers can be used in hole transport layers that contain charge-generating materials.
[0117] emission layer in intermediate layer 150
[0118] When the light-emitting device 10 is a full-color light-emitting device, the emitting layer can be patterned into a red emitting layer, a green emitting layer, and / or a blue emitting layer, depending on the sub-pixel. In one embodiment, the emitting layer may have a stacked structure of two or more layers selected from the red, green, and blue emitting layers, wherein the two or more layers are in contact with each other (e.g., physically in contact) or spaced apart from each other. In one or more embodiments, the emitting layer may contain two or more materials selected from the materials that emit red light, green light, and blue light, wherein the two or more materials are mixed with each other in a single layer to emit white light.
[0119] The emitting layer may comprise a host and dopants. Dopants may include phosphorescent dopants, fluorescent dopants, or any combination thereof.
[0120] Based on 100 parts by weight of the substrate, the amount of dopant in the emitter layer can be from about 0.01 parts by weight to about 15 parts by weight. However, embodiments of this disclosure are not limited thereto.
[0121] In one implementation, the emitter layer may contain quantum dots.
[0122] The thickness of the emission layer can be approximately to approximately For example, about to approximately When the thickness of the emitting layer is within these ranges, excellent light emission characteristics can be obtained without a significant increase in driving voltage.
[0123] The main body in the emission layer
[0124] The main body may include a compound represented by formula 301:
[0125] Formula 301
[0126] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 .
[0127] In Equation 301,
[0128] Ar 301 It can be substituted or unsubstituted C5-C 60 The carbocyclic group is either substituted or unsubstituted C1-C. 60 Heterocyclic groups,
[0129] xb11 can be 1, 2, or 3.
[0130] L 301It can be substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 arylene groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, or substituted or unsubstituted divalent nonaromatic fused heterocyclic groups,
[0131] xb1 can be 0, 1, 2, 3, 4, or 5.
[0132] R 301 It can be deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thioyl groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused 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 ),
[0133] xb21 can be 1, 2, 3, 4, or 5, and
[0134] Q 301 To Q 303 Regarding Q 11 The descriptions are the same.
[0135] For example, when xb11 in equation 301 is 2 or greater than 2, two or more Ar 301 They can be connected to each other via a single key.
[0136] In one or more embodiments, the body may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
[0137] Formula 301-1
[0138]
[0139] Formula 301-2
[0140]
[0141] In Equations 301-1 and 301-2,
[0142] Ring A 301 To Ring A 304 Each can be C5-C independently. 60 Carbocyclic groups or C1-C 60 Heterocyclic groups,
[0143] X 301 It can be O, S, N-[(L 304 ) xb4 -R 304 ]、C(R 304 (R) 305 ) or Si(R 304 (R) 305 ),
[0144] xb22 and xb23 can each be 0, 1, or 2 independently.
[0145] L 301 xb1 and R 301 Same as described above,
[0146] L 302 To L 304 They can be independently related to L 301 The descriptions are the same.
[0147] xb2 to xb4 can each be independently identical to the description of xb1, and
[0148] R302 To R 305 and R 311 To R 314 They can be independently related to R. 301 The descriptions are the same.
[0149] In one or more embodiments, the host may include an alkaline earth metal complex. For example, the host may be a Be complex (e.g., compound H55), a Mg complex, a Zn complex, or any combination thereof.
[0150] In one embodiment, the main body may include one or any combination of compounds H1 to H120, 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(carbazolyl-9-yl)benzene (mCP), and 1,3,5-tris(carbazolyl-9-yl)benzene (TCP), but embodiments of this disclosure are not limited thereto.
[0151]
[0152]
[0153]
[0154]
[0155]
[0156]
[0157] Phosphorescent dopants contained in the emission layer of intermediate layer 150
[0158] Phosphorescent dopants may contain at least one transition metal as the central metal (e.g., a central metal atom).
[0159] Phosphorescent dopants may include monodentate ligands, dipentate ligands, tridentate ligands, tetradentate ligands, pentadentate ligands, hexadentate ligands, or any combination thereof.
[0160] Phosphorescent dopants can be electrically neutral.
[0161] For example, phosphorescent dopants can include organometallic compounds represented by formula 401:
[0162] Formula 401
[0163] M(L 401 ) xc1(L 402 ) xc2
[0164] Formula 402
[0165]
[0166] In Equations 401 and 402,
[0167] 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), or thulium (Tm)).
[0168] L 401 The ligand can be represented by Equation 402, and xc1 can be 1, 2, or 3, wherein when xc1 is 2 or greater than 2, there are two or more L... 401 They can be the same or different from each other.
[0169] L 402 It can be an organic ligand, xc2 can be 0, 1, 2, 3 or 4, and when xc2 is 2 or greater than 2, there are two or more L... 402 They can be the same or different from each other.
[0170] X 401 and X 402 It can be either nitrogen or carbon, each independently.
[0171] Ring A 401 And Ring A 402 Each can be C5-C independently. 60 Carbocyclic groups or C1-C 60 Heterocyclic groups,
[0172] 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 = *',
[0173] X 403 and X 404 These can be chemical bonds (e.g., covalent or coordinate bonds), O, S, N (Q) independently. 413 ), B(Q) 413 ), P(Q 413 ), C(Q413 (Q) 414 ) or Si(Q 413 (Q) 414 ),
[0174] Q 411 To Q 414 They can be independently related to Q. 11 The descriptions are the same.
[0175] R 401 and R 402 Each of these groups can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, or substituted or unsubstituted C1-C. 20 Alkyl groups, substituted or unsubstituted C1-C 20 alkoxy group, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thioyl groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused 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 ),
[0176] Q 401 To Q 403 They can be independently related to Q. 11 The descriptions are the same.
[0177] xc11 and xc12 can each be an integer from 0 to 10 independently, and
[0178] In Equation 402, * and *' each represent the binding site with M in Equation 401.
[0179] In one or more embodiments, in formula 402, i)X 401 It can be nitrogen, and X 402 It can be carbon, or ii)X 401 and X 402 Each of them can be nitrogen.
[0180] In one or more embodiments, when xc1 in equation 401 is 2 or greater than 2, two or more L 401 The two rings A in 401 It can be optionally via T as a linking group 402 Connected to each other, or two or more L's 401 The two rings A in 402 It can be optionally via T as a linking group 403 They are interconnected (see compounds PD1 through PD4 and PD7). T 402 and T 403 They can be independently related to T 401 The descriptions are the same.
[0181] L in Equation 401 402 It can be an organic ligand. For example, L... 402 It can be a halogen group, a diketone group (e.g., an acetylacetonate group), a carboxylic acid group (e.g., a pyridine carboxylate group), a -C (=O) group, an isonitrile group, a -CN group, a phosphorus group (e.g., a phosphine group or a phosphite group), or any combination thereof, but the embodiments of this disclosure are not limited thereto.
[0182] Phosphorescent dopants may include, for example, one or any combination of the following compounds PD1 to PD25, but embodiments of this disclosure are not limited thereto:
[0183]
[0184] Fluorescent dopants in the emission layer
[0185] Fluorescent dopants may include arylamine compounds or styreneamine compounds.
[0186] For example, fluorescent dopants may include compounds represented by formula 501:
[0187] Formula 501
[0188]
[0189] In Equation 501,
[0190] Ar 501 It can be substituted or unsubstituted C5-C60 The carbocyclic group is either substituted or unsubstituted C1-C. 60 Heterocyclic groups,
[0191] L 501 To L 503 Each can be either substituted or unsubstituted C3-C independently. 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 arylene groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, or substituted or unsubstituted divalent nonaromatic fused heterocyclic groups,
[0192] xd1 to xd3 can each be 0, 1, 2 or 3 independently.
[0193] R 501 and R 502 Each can be either substituted or unsubstituted C3-C independently. 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thioyl groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, and
[0194] xd4 can be 1, 2, 3, 4, 5, or 6.
[0195] For example, Ar in Equation 501 501 It can be a fused cyclic ring composed of three or more monocyclic groups (e.g., anthracene groups, ...). (Groups, pyrene groups, etc.)
[0196] In one implementation, xd4 in Formula 501 can be 2, but the implementation of this disclosure is not limited thereto.
[0197] For example, fluorescent dopants may include one or any combination of the following compounds FD1 to FD36, DPVBi, DPAVBi:
[0198]
[0199]
[0200]
[0201] Quantum dots in the emitter layer
[0202] The emitter layer can contain quantum dots.
[0203] In this specification, the term "quantum dot" refers to a crystal of a semiconductor compound and may include any material that emits emission wavelengths of different lengths depending on the size of the crystal. Therefore, there are no particular limitations on quantum dot materials. The diameter of a quantum dot is not particularly limited, but can be, for example, from about 1 nm to about 10 nm.
[0204] Quantum dots can be synthesized and arranged in the emitter layer through wet chemical processes, organometallic chemical vapor deposition processes, molecular beam epitaxy processes and / or similar processes.
[0205] According to the wet chemical process, precursor materials are added to an organic solvent to grow quantum dot crystals. During crystal growth, the organic solvent acts as a dispersant that naturally coordinates to the surface of the quantum dot crystals and controls the crystal growth. In this respect, the wet chemical process can be easily performed compared to vapor deposition processes such as metal-organic chemical vapor deposition (MOCVD) and molecular beam epitaxy (MBE), and the growth of quantum dot particles can be controlled through a low-cost process.
[0206] In one embodiment, the quantum dot may include: group III-VI semiconductor compounds; group II-VI semiconductor compounds; group III-V semiconductor compounds; group IV-VI semiconductor compounds; group IV elements or compounds; or any combination thereof.
[0207] For example, III-VI semiconductor compounds may include: binary compounds, such as In2S3; ternary compounds, such as AgInS, AgInS2, CuInS, CuInS2, etc.; or any combination thereof.
[0208] For example, group II-VI semiconductor compounds may include: binary compounds, such as CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, etc.; ternary compounds, such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS, etc.; quaternary compounds, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, etc.; or any combination thereof.
[0209] For example, III-V semiconductor compounds may include: binary compounds, such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, etc.; ternary compounds, such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InNAs, InNSb, InPAs, InPSb, etc.; quaternary compounds, such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, etc.; or any combination thereof.
[0210] For example, group IV-VI semiconductor compounds may include: binary compounds, such as SnS, SnSe, SnTe, PbS, PbSe, PbTe, etc.; ternary compounds, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, etc.; quaternary compounds, such as SnPbSSe, SnPbSeTe, SnPbSTe, etc.; or any combination thereof.
[0211] For example, Group IV elements or compounds may include: single elements, such as Si, Ge, etc.; binary compounds, such as SiC, SiGe, etc.; or any combination thereof.
[0212] Each element contained in a binary, ternary, or quaternary compound may exist in the particle at a uniform or substantially uniform concentration, or may exist in the same particle in a state where the concentration distribution is partially different. For example, a binary, ternary, or quaternary compound may exist in the particle at a concentration that varies along a concentration gradient within the particle.
[0213] In one implementation, the quantum dot may have a single structure, in which each element present in the respective quantum dot is present in a uniform or substantially uniform concentration, or it may have a core-shell dual structure. For example, the material contained in the core may be different from the material contained in the shell.
[0214] The shell of a quantum dot can serve as a protective layer for maintaining semiconductor properties by preventing or reducing the chemical degradation or deterioration of the nucleus, and / or as a charging layer for imparting electrophoretic properties to the quantum dot. The shell can be a single layer or multiple layers. The interface between the nucleus and the shell can have a concentration gradient, where the concentration of elements present in the shell decreases towards the center of the quantum dot.
[0215] Examples of shells for quantum dots can include oxides of metals or nonmetals, semiconductor compounds, or any combination thereof. For example, oxides of metals or nonmetals can include binary compounds (e.g., SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, or NiO) or ternary compounds (e.g., MgAl2O4, CoFe2O4, NiFe2O4, or CoMn2O4), but embodiments of this disclosure are not limited thereto. Furthermore, semiconductor compounds can include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, etc., but embodiments of this disclosure are not limited thereto.
[0216] The full width at half maximum (FWHM) of the emission wavelength spectrum of quantum dots can be about 45 nm or less, for example, about 40 nm or less, or about 30 nm or less. When the FWHM of the emission wavelength spectrum of quantum dots is within this range, color purity or color reproducibility can be improved. Furthermore, light emitted through such quantum dots can be omnidirectional, thereby improving wide viewing angles.
[0217] Furthermore, quantum dots can be, for example, spherical, pyramidal, multi-armed or cubic nanoparticles, nanotubes, nanowires, nanofibers or nanoplate particles, but embodiments of the present disclosure are not limited thereto.
[0218] 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. Therefore, by using quantum dots of different sizes, light-emitting devices that emit light of various wavelengths can be realized. More specifically, the size of the quantum dots can be selected to emit red, green, and / or blue light. Furthermore, by configuring the size of the quantum dots, various colors of light can be combined to emit white light.
[0219] Electron transport region in intermediate layer 150
[0220] The electron transport region may have i) a single-layer structure comprising (or consisting of): a single layer containing a single material (or consisting of a single material), ii) a single-layer structure comprising (or consisting of): a single layer containing multiple different materials (or consisting of multiple different materials), or iii) a multi-layer structure comprising multiple layers containing different materials.
[0221] The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof, but the embodiments of this disclosure are not limited thereto.
[0222] For example, the electron transport region can 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 for each structure, the constituent layers are stacked sequentially from the emitter layer. However, the implementation scheme of the electron transport region structure is not limited to this.
[0223] The electron transport region (e.g., a buffer layer, hole blocking layer, electron control layer, or electron transport layer in the electron transport region) may contain a metal-free compound having at least one cyclic group of nitrogen containing π-electron-deficient nitrogen that can readily accept electrons.
[0224] "A cyclic group containing nitrogen lacking π electrons" can be a C1-C group having at least one *-N=*' moiety as the cyclic moiety. 60 Heterocyclic groups.
[0225] For example, a "cyclic group containing π-electron-deficient nitrogen" can be i) a first ring, ii) a fused cyclic group in which two or more first rings are fused together (e.g., bonded together), or iii) a fused cyclic group in which at least one first ring and at least one second ring are fused together, wherein the first ring is a heteromonocyclic group (e.g., imidazole group, pyridine group, triazine group, etc.) containing at least one *-N=*' portion as the cyclic moiety, and the second ring is a cyclic group (e.g., phenyl group, dibenzofuran group, carbazole group, etc.) that does not contain a *-N=*' portion as the cyclic moiety.
[0226] Examples of cyclic groups containing nitrogen lacking π electrons include pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, benzoquinoline, isoquinoline, benzoisoquinoline, quinoxaline, benzoquinoxaline, quinazoline, benzoquinazoline, phenanthrene, phthalazine, naphthidine, azacarbazole, azafluorene, azadibenzothiophene, azadibenzothiophene, and azadibenzofuran. The groups include pyrazole groups, imidazole groups, triazole groups, tetraazole groups, oxazole groups, isoxazole groups, thiazole groups, isothiazole groups, oxadiazole groups, thiadiazole groups, benzopyrazole groups, benzimidazole groups, benzoxazole groups, benzothiazole groups, benzoxadiazole groups, benzothiadiazole groups, imidazopyridine groups, imidazopyrimidine groups, imidazotriazine groups, imidazopyrazine groups, and imidazopyridazine groups, but embodiments of the present disclosure are not limited thereto.
[0227] For example, the electron transport region may comprise a compound represented by Formula 601 and containing at least one cyclic group of nitrogen lacking π electrons:
[0228] Formula 601
[0229] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .
[0230] In Equation 601,
[0231] Ar 601 It can be substituted or unsubstituted C5-C 60 The carbocyclic group is either substituted or unsubstituted C1-C. 60 Heterocyclic groups,
[0232] xe11 can be 1, 2, or 3.
[0233] L 601 It can be substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 arylene groups, substituted or unsubstituted C1-C 60Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, or substituted or unsubstituted divalent nonaromatic fused heterocyclic groups,
[0234] xe1 can be 0, 1, 2, 3, 4, or 5.
[0235] R 601 It can be substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thioyl groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused 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 ),
[0236] Q 601 To Q 603 They can be independently related to Q. 11 The same description, and
[0237] xe21 can be 1, 2, 3, 4 or 5.
[0238] For example, Ar of Formula 601 601 L 601 and R 601 At least one of them can independently contain at least one nitrogen ring that is π-deficient.
[0239] In one or more embodiments, when xe11 in formula 601 is 2 or greater than 2, two or more Ar 601 They can be connected to each other via a single key.
[0240] In one implementation, Ar in Formula 601 601 It can be a substituted or unsubstituted anthracene group.
[0241] In one embodiment, the electron transport region may comprise a compound represented by formula 601-1:
[0242] Formula 601-1
[0243]
[0244] In Equation 601-1,
[0245] 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 ), and X 614 To X 616 At least one of them can be N,
[0246] L 611 To L 613 Each can be related to L. 601 The descriptions are the same.
[0247] xe611 to xe613 can each be identical to the description concerning xe1.
[0248] R 611 To R 613 Each can be related to R. 601 The same description, and
[0249] R 614 To R 616 Each of these can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, phenyl group, biphenyl group, terphenyl group or naphthyl group.
[0250] For example, xe1 and xe611 to xe613 in Equations 601 and 601-1 can each be 0, 1 or 2 independently.
[0251] The electron transport region may contain one or any combination of the following compounds ET1 to ET36, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, TAZ, and NTAZ, but embodiments of this disclosure are not limited thereto:
[0252]
[0253]
[0254] The thicknesses of the buffer layer, hole-blocking layer, and electronic control layer can each be approximately [value missing]. to approximately For example, about to approximately When the thicknesses of the buffer layer, hole blocking layer, and electronic control layer are within these ranges, excellent hole blocking characteristics or excellent electronic control characteristics can be obtained without a significant increase in driving voltage.
[0255] The thickness of the electron transport layer can be approximately to approximately For example, about to approximately When the thickness of the electron transport layer is within the range described above, the electron transport layer can have suitable or satisfactory electron transport characteristics without a significant increase in driving voltage.
[0256] In addition to the materials described above, the electron transport region (e.g., the electron transport layer in the electron transport region) may further contain a metallic material.
[0257] Metal-containing materials may include alkali metal complexes, alkaline earth metal complexes, or any combination thereof. The metal ion in an alkali metal complex may be Li, Na, K, Rb, or Cs ions, and the metal ion in an alkaline earth metal complex may be Be, Mg, Ca, Sr, or Ba ions. The ligand coordinating with the metal ion in the alkali metal or alkaline earth metal complex may be hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthrene, cyclopentadiene, or any combination thereof, but the embodiments disclosed herein are not limited to these.
[0258] For example, metal-containing materials may include Li complexes. Li complexes may include, for example, compounds ET-D1 (LiQ) or ET-D2:
[0259]
[0260] The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 190. The electron injection layer may be in direct contact (e.g., physical contact) with the second electrode 190.
[0261] The electron injection layer may have i) a single-layer structure, which includes the following (or consists of the following): a single layer containing a single material (or consisting of a single material), ii) a single-layer structure, which includes the following (or consists of the following): a single layer containing a plurality of different materials (or consisting of a plurality of different materials), or iii) a multi-layer structure, which includes a plurality of layers containing different materials.
[0262] The electron injection layer may contain 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.
[0263] The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
[0264] The compounds containing an alkali metal, the compounds containing an alkaline earth metal, and the compounds containing a rare earth metal may be oxides and halides (e.g., fluorides, chlorides, bromides, or iodides) of the alkali metal, the alkaline earth metal, and the rare earth metal, or any combination thereof.
[0265] The compound containing an alkali metal may be an alkali metal oxide (e.g., Li2O, Cs2O, or K2O) and an alkali metal halide (e.g., LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI), or any combination thereof. The compound containing an alkaline earth metal may include an alkaline earth metal oxide, such as BaO, SrO, CaO, Ba x Sr 1-x O(0 < x < 1) or Ba x Ca 1-x O(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.
[0266] The alkali metal complex, the alkaline earth metal complex, and the rare earth metal complex may contain i) one of the ions of the alkali metal, the alkaline earth metal, and the rare earth metal, and ii) ligands connected to the metal ion, such as 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, but the embodiments of the present disclosure are not limited thereto.
[0267] The electron-injected layer comprises (or is composed of) alkali metals, alkaline earth metals, rare earth metals, alkali metal-containing compounds, alkaline earth metal-containing compounds, rare earth metal-containing compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof, or may further comprise organic materials (e.g., compounds represented by Formula 601). When the electron-injected layer further comprises organic materials, the alkali metals, alkaline earth metals, rare earth metals, alkali metal-containing compounds, alkaline earth metal-containing compounds, rare earth metal-containing compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof may be uniformly or non-uniformly dispersed in the matrix containing the organic materials.
[0268] The thickness of the electron injection layer can be approximately to approximately For example, about to approximately When the thickness of the electron injection layer is within the range described above, the electron injection layer can have suitable or satisfactory electron injection characteristics without a significant increase in driving voltage.
[0269] Second electrode 190
[0270] The second electrode 190 may be located on the intermediate layer 150 having such a structure. The second electrode 190 may be a cathode serving as an electron injection electrode, and may be made of metals, alloys, conductive compounds, or any combination thereof, each having a low work function, as materials for forming the second electrode 190.
[0271] The second electrode 190 may comprise lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ITO, IZO, or any combination thereof, but the embodiments disclosed herein are not limited thereto. The second electrode 190 may be a transmission electrode, a semi-transmission electrode, or a reflection electrode.
[0272] The second electrode 190 may have a single-layer structure or a multi-layer structure including two or more layers.
[0273] Cover layer
[0274] 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 190. More specifically, the light-emitting device 10 may have a structure in which the first cover layer, the first electrode 110, the intermediate layer 150, and the second electrode 190 are stacked in a predetermined order, or in which the first cover layer, the first electrode 110, the intermediate layer 150, the second electrode 190, and the second cover layer are stacked in a predetermined order.
[0275] Light generated in the emitting layer of the intermediate layer 150 of the light-emitting device 10 can be led outward through the first electrode 110 and the first cover layer, each of which can be semi-transparent or transmissive. Alternatively, light generated in the emitting layer of the intermediate layer 150 of the light-emitting device 10 can be led outward through the second electrode 190 and the second cover layer, each of which can be semi-transparent or transmissive.
[0276] The first and second capping layers can increase the external luminescence efficiency based on the principle of constructive interference.
[0277] The first and second covering layers can each be independently an organic covering layer containing organic materials, an inorganic covering layer containing inorganic materials, or a composite covering layer containing both organic and inorganic materials.
[0278] At least one of the first and second capping layers may independently comprise a carbocyclic compound, a heterocyclic compound, an amine-containing compound, a porphyrin derivative, a phthalocyanine derivative, a naphthylphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or a combination thereof. The carbocyclic compound, heterocyclic compound, and amine-containing compound may optionally be substituted with substituents containing O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In one embodiment, at least one of the first and second capping layers may independently comprise an amine-containing compound.
[0279] For example, at least one of the first and second capping layers may each independently contain a compound represented by formula 201, a compound represented by formula 202, or any combination thereof.
[0280] In one or more embodiments, at least one of the first and second capping layers may each independently comprise a compound selected from compounds HT28 to HT33, compounds CP1 to CP5, and any combination thereof, but the embodiments of this disclosure are not limited thereto:
[0281]
[0282] equipment
[0283] The light-emitting device can be included in a variety of suitable devices. For example, a light-emitting device, a verification device, or an electronic device that includes the light-emitting device can be provided.
[0284] In addition to the light-emitting device, the light-emitting device may further include a color filter. The color filter may be located in at least one direction of travel of the light emitted from the light-emitting device. For example, the light emitted from the light-emitting device may be blue light, but embodiments of this disclosure are not limited thereto. The light-emitting device can be understood by referring to its description provided above.
[0285] The light-emitting device may include a first substrate. The first substrate may include multiple sub-pixel regions, and the color filter may include multiple color filter regions corresponding to the multiple sub-pixel regions.
[0286] A pixel-defining film can be located between multiple sub-pixel regions to define each of the sub-pixel regions.
[0287] The color filter may further include a light-blocking pattern located between multiple color filter regions.
[0288] Multiple color filter regions may include: a first color filter region emitting a first color light; a second color filter region emitting a second color light; and / or a third color filter region emitting a third color light, wherein the first color light, the second color light, and the third color light may have different maximum emission wavelengths from each other. For example, 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, but embodiments of this disclosure are not limited thereto. For example, each of the multiple color filter regions may contain a quantum dot, but embodiments of this disclosure are not limited thereto. More specifically, the first color filter region may contain red quantum dots, the second color filter region may contain green quantum dots, and the third color filter region may not contain quantum dots. Quantum dots can be understood by referring to their description provided above. The first color filter region, the second color filter region, and / or the third color filter region may each contain a scattering agent, but embodiments of this disclosure are not limited thereto.
[0289] For example, the light-emitting device can emit a first light, a first color filter region can absorb the first light to emit a first-first-color light, a second color filter region can absorb the first light to emit a second-first-color light, and a third color filter region can absorb the first light to emit a third-first-color light. In this respect, the first-first-color light, the second-first-color light, and the third-first-color light can have different maximum emission wavelengths from each other. More specifically, 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, but embodiments of this disclosure are not limited thereto.
[0290] In addition to the light-emitting device 10 described above, the light-emitting 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 either the source electrode or the drain electrode may be electrically connected to either the first electrode or the second electrode of the light-emitting device.
[0291] Thin-film transistors may further include gate electrodes, gate insulating layers, etc.
[0292] The active layer may include crystalline silicon, amorphous silicon, organic semiconductors, oxide semiconductors, etc., but the embodiments disclosed herein are not limited to these.
[0293] The light-emitting device may further include a sealing portion for sealing the light-emitting device 10. The sealing portion may be located between the color filter and the light-emitting device 10. The sealing portion allows light from the light-emitting device 10 to be drawn to the outside while simultaneously (or concurrently) preventing or reducing the penetration of external air and / or moisture into the light-emitting device 10. The sealing portion may be a sealing substrate comprising a transparent glass or plastic substrate. The sealing portion may be a thin-film encapsulation layer comprising multiple organic layers and / or multiple inorganic layers. When the sealing portion is a thin-film encapsulation layer, the light-emitting device may be flexible.
[0294] Light-emitting devices can be used as various suitable displays, light sources, etc.
[0295] The verification device can be, for example, a biometric verification device for verifying an individual by using biometric information from a biometric body (e.g., fingertip, pupil, etc.).
[0296] In addition to the light-emitting device, the verification device may further include a biometric information collector.
[0297] Electronic devices can be applied to personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, video game consoles, medical instruments (e.g., electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram (ECG) displays, ultrasound diagnostic devices, or endoscopic displays), fish finders, various suitable measuring instruments, meters (e.g., instruments for vehicles, aircraft, and ships), projectors, etc., but embodiments of this disclosure are not limited thereto.
[0298] Preparation method
[0299] Layers constituting hole transport regions, emission regions, and electron transport regions can be formed in a specific region using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser-induced thermal imaging.
[0300] When forming layers constituting hole transport regions, emission regions, and electron transport regions by vacuum deposition, considering the materials to be included in the layers to be formed and the structure of the layers to be formed, a deposition temperature of about 100°C to about 500°C and a deposition time of about 10 -8 To about 10 -3 The vacuum degree and about to approximately Deposition occurs at a certain deposition rate.
[0301] When spin coating is used to form layers constituting hole transport regions, emission regions, and electron transport regions, spin coating can be performed at a coating rate of about 2,000 rpm to about 5,000 rpm and a heat treatment temperature of about 80°C to about 200°C, taking into account the materials to be included in the layers to be formed and the structure of the layers to be formed.
[0302] At least some general definitions of substituents
[0303] As used in this article, the term "C1-C" 60"Alkyl group" refers to a monovalent group of a straight-chain or branched aliphatic hydrocarbon having 1 to 60 carbon atoms, and examples 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 groups. The term "C1-C" is used herein. 60 "alkylene group" refers to a group that has a C1-C2 bond structure. 60 Alkyl groups are divalent groups with essentially the same structure.
[0304] As used in this article, the term "C2-C" 60 "Alkenyl group" refers to the group located at C2-C. 60 A monovalent hydrocarbon group having at least one carbon-carbon double bond at the main chain (e.g., middle) or end (e.g., tip) of an alkyl group, and examples include vinyl groups, propenyl groups, and butenyl groups. As used herein, the term "C2-C" is used... 60 "Ideinyl group" refers to a group that has a C2-C... 60 Alkenyl groups are divalent groups with essentially the same structure.
[0305] As used in this article, the term "C2-C" 60 "Alkyne group" refers to the group located at C2-C. 60 A monovalent hydrocarbon group having at least one carbon-carbon triple bond at the main chain (e.g., middle) or end (e.g., tip) of an alkyl group, and examples include ethynyl and propynyl groups. As used herein, the term "C2-C" is used in this context. 60 "Imyynyl group" refers to a group that has a C2-C... 60 Alkyne groups are divalent groups with essentially the same structure.
[0306] As used in this article, the term "C1-C" 60 "Alkoxy group" refers to the group consisting of -OA 101 (where A) 101 For C1-C 60 Alkyl groups are monovalent groups, and examples of them include methoxy groups, ethoxy groups and isopropoxy groups.
[0307] As used in this article, the term "C3-C" 10"Cycloalkyl group" refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and examples of such groups are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, and bicyclo[2.2.2]octyl. As used herein, the term "C3-C" is also relevant. 10 "Cycloalkylene group" refers to a group that has a C3-C6 bond structure. 10 Cycloalkyl groups are divalent groups with essentially the same structure.
[0308] As used in this article, the term "C1-C" 10 "Heterocyclic alkyl group" refers to a monovalent cyclic group having 1 to 10 carbon atoms containing a heteroatom (e.g., N, O, Si, P, S, or any combination thereof) as a cyclic atom, and examples are 1,2,3,4-oxatriazole alkyl groups, tetrahydrofuranyl groups, and tetrahydrothiophenyl groups. As used herein, the term "C1-C..." is also used. 10 "Heterocyclic alkyl groups" refers to groups with C1-C2 groups. 10 Heterocyclic alkyl groups are divalent groups with essentially the same structure.
[0309] As used in this article, the term "C3-C" 10 "Cycloalenyl group" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and lacking aromaticity (e.g., non-aromatic), and non-limiting examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl groups. As used herein, the term "C3-C" is also relevant. 10 "Iridyl group" refers to a group that has a C3-C6 bond structure. 10 Cycloalkenyl groups are divalent groups with essentially the same structure.
[0310] As used in this article, the term "C1-C" 10 A "heterocyclic alkenyl group" refers to a monovalent cyclic group having one to ten carbon atoms, containing a heteroatom (e.g., N, O, Si, P, S, or any combination thereof) as a cyclic atom, wherein the ring has at least one double bond. C1-C 10 Examples of heterocyclic alkenyl groups are 4,5-dihydro-1,2,3,4-oxarizolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothiophenyl groups. As used herein, the term "C1-C..." 10 "Heterocyclic alkenyl group" refers to a group that has a C1-C2 bond structure. 10 Heterocyclic alkenyl groups are divalent groups with essentially the same structure.
[0311] As used in this article, the term "C6-C" 60"Aryl group" refers to a monovalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms, and as used herein, "C6-C..." 60 "Aromatic group" refers to a divalent group that has a carbocyclic aromatic system containing 6 to 60 carbon atoms. (C6-C) 60 Examples of aryl groups include phenyl groups, heptalenyl groups, naphthyl groups, chamomile cycloyl groups, indoleyl groups, acenaphthenic groups, phenanthreneyl groups, anthraceneyl groups, fluoranthraceneyl groups, benzo[a]phenanthreneyl groups, and pyreneyl groups. Peryl group, peryl group, pentaphenyl group, heptalenyl group, tetraphenyl group, fusyl group, hexaphenyl group, pentaphenyl group, rutinyl group, keratyl group, and ovoidyl group. When C6-C 60 aryl groups and C6-C 60 When each of the aryl groups contains two or more rings, the two or more rings may be fused together (e.g., joined together).
[0312] As used in this article, the term "C1-C" 60 "Heteroaryl group" refers to a monovalent heterocyclic aromatic system having a heteroatom (e.g., N, O, Si, P, S or any combination thereof) as a cyclic atom and 1 to 60 carbon atoms, and is referred to herein as "C1-C". 60 "Hypo-aryl group" refers to a divalent heterocyclic aromatic system having a heteroatom (e.g., N, O, Si, P, S or any combination thereof) as a cyclic atom and 1 to 60 carbon atoms. C1-C 60 Examples of heteroaryl groups are pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, benzo[a]quinolinyl, isoquinolinyl, benzo[a]isoquinolinyl, quinoxalinyl, benzo[a]quinoxalinyl, quinazolinyl, benzo[a]quinazolinyl, phenanthrolinel, phthalazinyl, and naphthidyl. When C1-C 60 heteroaryl groups and C1-C 60 When each of the heteroaryl groups comprises two or more rings, the two or more rings may be fused together (e.g., joined together).
[0313] As used in this article, the term "C6-C" 60 "Aryloxy group" refers to -OA 102 (where A) 102 For C6-C 60 (aryl group), and as used herein by the term "C6-C" 60 "Aryl thio group" refers to -SA 103 (where A) 103 For C6-C60 (aryl group).
[0314] As used herein, the term "monovalent nonaromatic fused polycyclic group" refers to a monovalent group (e.g., having 8 to 60 carbon atoms) having two or more rings fused together (e.g., bonded together), containing only carbon atoms as cyclic atoms, and lacking aromaticity throughout its molecular structure (e.g., the entire molecular structure is not aromatic). Examples of monovalent nonaromatic fused polycyclic groups are indenyl groups, fluorenyl groups, spiro-difluorenyl groups, benzo[a]fluorenyl groups, indo[a]phenanthryl groups, and indo[a]anthrayl groups. As used herein, the term "divalent nonaromatic fused polycyclic group" refers to a divalent group having a structure substantially the same as that of a monovalent nonaromatic fused polycyclic group.
[0315] As used herein, the term “monovalent nonaromatic fused heterocyclic group” refers to a monovalent group in which two or more rings are fused together (e.g., bonded together), which contains heteroatoms other than carbon (e.g., N, O, Si, P, and S or any combination thereof) as cyclic atoms and is non-aromatic throughout its molecular structure (e.g., the entire molecular structure is not aromatic). Examples of monovalent non-aromatic fused heterocyclic groups include pyrrolyl groups, thiophenyl groups, furanyl groups, indole groups, benzoindole groups, naphthoindole groups, isoindole groups, benzoisoindole groups, naphthoisoindole groups, benzothiolyl groups, benzothiphenyl groups, benzofuranyl groups, carbazole groups, dibenzothiolyl groups, dibenzothiphenyl groups, dibenzofuranyl groups, azacarbazoleyl groups, azafluorenyl groups, azadibenzothiolyl groups, azadibenzothiphenyl groups, azadibenzofuranyl groups, pyrazolyl groups, imidazoleyl groups, triazoleyl groups, tetraazoleyl groups, oxazolyl groups, isoxazolyl groups, thiolyl groups, isothiazolyl groups, and oxadiazoleyl groups. Thiadiazolyl group, benzopyrazolyl group, benzoimidazolyl group, benzooxazolyl group, benzothiazolyl group, benzooxadiazolyl group, benzothiadiazolyl group, imidazopyridyl group, imidazopyrimidine group, imidazotriazinyl group, imidazopyrazinyl group, imidazopyridazinyl group, indolecarbazoyl group, indolocarbazoyl group, benzofuranocarbazoyl group, benzothiophenocarbazoyl group, benzothiophenocarbazoyl group, benzoindolocarbazoyl group, benzocarbazoyl group, benzonaphthiophenyl group, benzonaphthiophenyl group, benzofuranodibenzofuranyl group, benzofuranodibenzothiophenyl group and benzothiophenodibenzothiophenyl group. As used in this article, the term "divalent nonaromatic fused heterocyclic group" refers to a divalent group having a structure substantially the same as that of a monovalent nonaromatic fused heterocyclic group.
[0316] As used in this article, the term "C5-C" 60 A "carbocyclic group" refers to a monocyclic or polycyclic group that contains only carbon as the cyclic atom and consists of 5 to 60 carbon atoms (or is composed of 5 to 60 carbon atoms). (C5-C) 60 The carbocyclic group can be an aromatic carbocyclic group or a non-aromatic carbocyclic group. C5-C 60 The carbocyclic group can be a compound (e.g., benzene), a monovalent group (e.g., a phenyl group), or a divalent group (e.g., a phenylene group). In one or more embodiments, depending on the linkage to C5-C... 60 The number of substituents in the carbocyclic group, C5-C 60 The carbon ring group can be a trivalent group or a tetravalent group.
[0317] C5-C 60 Examples of carbocyclic groups include cyclopentadienyl groups, phenyl groups, pentanenyl groups, naphthyl groups, chamomile ring groups, indole groups, acenaphthene groups, phenanthrene groups, anthracene groups, fluoranthene groups, benzo[a]phenanthrene groups, and pyrene groups. Groups, perylene groups, pentaphenyl groups, heptadiene groups, tetraphenyl groups, argentide groups, hexaphenyl groups, pentaphenyl groups, rutin groups, argentide groups, ovoid groups, indole groups, fluorene groups, spiro-difluorene groups, benzo[a]fluorene groups, indo[a]phenanthrene groups, and indo[a]anthracene groups.
[0318] As used in this article, the term "C1-C" 60 A "heterocyclic group" refers to a monocyclic or polycyclic group containing 1 to 60 carbon atoms and heteroatoms other than carbon that act as cyclic atoms (e.g., N, O, Si, P, S, or any combination thereof). C1-C 60 The heterocyclic group can be an aromatic heterocyclic group or a non-aromatic heterocyclic group. C1-C 60 The heterocyclic group can be a compound (e.g., pyridine), a monovalent group (e.g., a pyridyl group), or a divalent group (e.g., a pyridylene group). In one or more embodiments, depending on the linkage to C1-C... 60 The number of substituents in the heterocyclic group, C1-C 60 Heterocyclic groups can be trivalent or tetravalent.
[0319] C1-C 60Examples of heterocyclic groups include pyridine groups, pyrimidine groups, pyrazine groups, pyridazine groups, triazine groups, quinoline groups, benzoquinoline groups, isoquinoline groups, benzoisoquinoline groups, quinoxaline groups, benzoquinoxaline groups, quinazoline groups, benzoquinazoline groups, phenanthrene groups, phthalazine groups, naphthidine groups, pyrrole groups, thiophene groups, furan groups, indole groups, benzoindole groups, naphthoindole groups, isoindole groups, benzoisoindole groups, naphthoisoindole groups, benzothiophene groups, benzofuran groups, carbazole groups, dibenzothiophene groups, dibenzothiophene groups, dibenzofuran groups, azacarbazole groups, azafluorene groups, azadibenzothiophene groups, azadibenzothiophene groups, azadibenzofuran groups, and pyrazole groups. Imidazole group, triazole group, tetraazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimazole group, benzoxazole group, benzothiazole group, benzooxadiazole group, benzothiadiazole group, imidazopyridine group, imidazopyrimidine group, imidazotriazine group, imidazopyrazine group, imidazopyridazine group, indolecarbazole group, indolecarbazole group, benzofurancarbazole group, benzothiophenecarbazole group, benzothiophenecarbazole group, benzoindolecarbazole group, benzocarbazole group, benzonaphthiophene group, benzonaphthiophene group, benzofurandibenzofuran group, benzofurandibenzothiophene group and benzothiophenedibenzothiophene group.
[0320] Replacement C5-C 60 Carbocyclic groups, substituted C1-C 60 Heterocyclic groups, substituted C1-C 60 alkylene groups, substituted C2-C 60 imide groups, substituted C3-C 10 Cycloalkyl groups, substituted C1-C 10 Heterocyclic alkyl groups, substituted C3-C 10 Cycloalkylene groups, substituted C1-C 10 Heterocyclic alkenyl groups, substituted C6-C 60 arylene groups, substituted C1-C 60 Heteroaryl groups, substituted divalent nonaromatic fused polycyclic groups, substituted divalent nonaromatic fused heterocyclic groups, substituted C1-C 60 Alkyl groups, substituted C2-C 60 alkenyl groups, substituted C2-C 60 alkynyl group, substituted C1-C 60 alkoxy groups, substituted C3-C 10 Cycloalkyl groups, substituted C1-C 10Heterocyclic alkyl groups, substituted C3-C 10 Cycloalkenyl groups, substituted C1-C 10 Heterocyclic alkenyl groups, substituted C6-C 60 aryl group, substituted C6-C 60 aryloxy groups, substituted C6-C 60 aryl thiols, substituted C1-C 60 The substituents of heteroaryl groups, substituted monovalent nonaromatic fused polycyclic groups, and substituted monovalent nonaromatic fused heterocyclic groups can each be:
[0321] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group or nitro group;
[0322] Each of the following is an unsubstituted or replaced group: -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 cycloalkenyl groups, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 aryl thiol groups, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -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 ) or -P(=O)(Q 11 (Q) 12 ) Replaced C1-C 60 Alkyl groups, C2-C 60 alkenyl groups, C2-C 60 alkynyl group or C1-C 60 Alkoxy group;
[0323] Each of the following is an unsubstituted or replaced group: -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 60 Alkyl groups, C2-C 60 alkenyl groups, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 cycloalkenyl groups, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 aryl thiol groups, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -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 ) or -P(=O)(Q 21 (Q) 22 ) Replaced C3-C 10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 cycloalkenyl groups, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 aryl thiol groups, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups;
[0324] -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 );or
[0325] Any combination thereof.
[0326] In this specification, Q 11 To Q 13 Q 21 To Q 23 and Q 31To Q 33 Each of these can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 60 Alkyl groups, C2-C 60 alkenyl groups, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 cycloalkenyl groups, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, biphenyl groups, or terphenyl groups.
[0327] As used herein, the term "Ph" refers to a phenyl group, "Me" refers to a methyl group, "Et" refers to an ethyl group, and "tert-Bu" or "Bu" refers to a tert-Bu group. t "" refers to the tert-butyl group, and as used herein, the term "OMe" refers to the methyl methacrylate group.
[0328] As used in this article, the term "biphenyl group" refers to a "phenyl group substituted with a phenyl group." In other words, a "biphenyl group" is a group with a C6-C6 bond. 60 The aryl group is a substituted phenyl group.
[0329] As used in this article, the term "terphenyl group" refers to a "phenyl group substituted with a biphenyl group." In other words, a "terphenyl group" is a phenyl group with a C6-C substituted group. 60 C6-C substituted with aryl group 60 The aryl group is a substituted phenyl group.
[0330] Unless otherwise defined, as used herein, * and *' each refer to the binding site with the adjacent atom in the corresponding formula.
[0331] The compounds and luminescent devices according to the embodiments will be described in more detail below with reference to the examples. The phrase "using B instead of A" used to describe the synthesis examples indicates that an equimolar amount of B is used instead of A.
[0332] Example
[0333] Manufacturing of light-emitting devices
[0334] Comparative Example 1
[0335] Will The glass substrate (anode) was cut to a size of 50mm × 50mm × 0.7mm, ultrasonicated with isopropanol and pure water for 5 minutes each, and then cleaned by exposure to ultraviolet light and ozone for 30 minutes. The ITO glass substrate was then fed into a vacuum deposition apparatus.
[0336] On an ITO glass substrate, compound HT1 and p-dopant (HAT-CN) were vacuum deposited at a weight ratio of 1:0.1 to form a structure with... A p-doped hole transport layer of a certain thickness is formed, and then compound HT1, which is used to form the hole transport layer, is vacuum deposited on it to form a layer with... A hole transport layer of a certain thickness.
[0337] On the hole transport layer, compound 1 and p-dopant (HAT-CN) were formed at a weight ratio of 1:0.1. The thickness, and then compound 1 is vacuum deposited on it to form a shape with A launch auxiliary layer of a certain thickness.
[0338] On the emitter-assisted layer, mCP and dopant (PD13) as the single host are co-deposited at a weight ratio of 90:10 to form a layer with The thickness of the emission layer.
[0339] Next, TSPO1, a compound used to form an electron transport layer, is formed on the emitter layer to form a structure with... An electron transport layer of a certain thickness is formed thereon, and TPBI, a compound used to form an electron injection layer, is formed thereon to form an electron transport layer with a thickness of [missing information]. An electron-injected layer of a certain thickness.
[0340] AgMg was vacuum deposited onto the electron-injected layer to form a structure with... A cathode with a thickness of 10% is used to complete the fabrication of an organic light-emitting device.
[0341]
[0342] Comparative Example 2
[0343] The light-emitting device was manufactured in essentially the same manner as in Comparative Example 1, but when forming the emission auxiliary layer, only Compound 1 was used without the p-dopant to form a light-emitting device. A launch auxiliary layer of a certain thickness.
[0344] Comparative Example 3
[0345] The light-emitting device was manufactured in essentially the same manner as in Comparative Example 1, except that compound 2 was used instead of compound 1 when forming the emission auxiliary layer.
[0346]
[0347] Comparative Example 4
[0348] The light-emitting device was manufactured in essentially the same manner as in Comparative Example 1, but when forming the emission auxiliary layer, only Compound 2 was used instead of the p-dopant to form a light-emitting device. A launch auxiliary layer of a certain thickness.
[0349] Comparative Example 5
[0350] The light-emitting device was manufactured in essentially the same manner as in Comparative Example 1, but when forming the emission auxiliary layer, compound 1 and compound 2 were used only in a 5:5 weight ratio without the use of a p-dopant to form a light-emitting device. A launch auxiliary layer of a certain thickness.
[0351] Comparative Example 6
[0352] The light-emitting device was manufactured in essentially the same manner as in Comparative Example 1, but when forming the emission auxiliary layer, compound 1 and compound 3 were used only in a 5:5 weight ratio without the use of a p-dopant to form a light-emitting device. A launch auxiliary layer of a certain thickness.
[0353]
[0354] Comparative Example 7
[0355] The light-emitting device was manufactured in essentially the same manner as in Comparative Example 1, but when forming the emission auxiliary layer, compound 2 and compound 4 were used only in a 5:5 weight ratio without the use of p-dopants to form a light-emitting device. A launch auxiliary layer of a certain thickness.
[0356]
[0357] Comparative Example 8
[0358] The light-emitting device was manufactured in essentially the same manner as in Comparative Example 1, but when forming the emitting layer, a premixed body comprising HT and ET in a weight ratio of 7:3 was used instead of a single body.
[0359]
[0360] Comparative Example 9
[0361] The light-emitting device was manufactured in essentially the same manner as in Comparative Example 2, but when forming the emitting layer, a premixed body comprising HT and ET in a weight ratio of 7:3 was used instead of a single body.
[0362] Comparative Example 10
[0363] The light-emitting device was manufactured in essentially the same manner as in Comparative Example 3, but when forming the emitting layer, a premixed body comprising HT and ET in a weight ratio of 7:3 was used instead of a single body.
[0364] Comparative Example 11
[0365] The light-emitting device was manufactured in essentially the same manner as in Comparative Example 4, but when forming the emitting layer, a premixed body comprising HT and ET in a weight ratio of 7:3 was used instead of a single body.
[0366] Comparative Example 12
[0367] The light-emitting device was manufactured in essentially the same manner as in Comparative Example 6, but when forming the emitting layer, a premixed body comprising HT and ET in a weight ratio of 7:3 was used instead of a single body.
[0368] Comparative Example 13
[0369] The light-emitting device was manufactured in essentially the same manner as in Comparative Example 7, but when forming the emitting layer, a premixed body comprising HT and ET in a weight ratio of 7:3 was used instead of a single body.
[0370] Comparative Example 14
[0371] The light-emitting device was manufactured in essentially the same manner as in Comparative Example 1, but NPB was used to form the hole transport layer, a premixed host comprising HT and ET in a 7:3 weight ratio was used instead of a single host to form the emission layer, and compounds HT2 and 2-21 were used only in a 5:5 weight ratio to form the emission auxiliary layer without using p-dopersies to form a light-emitting device with… A launch auxiliary layer of a certain thickness.
[0372]
[0373] Example 1
[0374] The light-emitting device was manufactured in essentially the same manner as in Comparative Example 1, but a premixed host comprising HT and ET in a 7:3 weight ratio was used instead of a single host when forming the emitting layer, and on the hole transport layer, compound 1 and compound 2 were used only in a 5:5 weight ratio without p-dopers to form a light-emitting device with… A launch auxiliary layer of a certain thickness.
[0375] Example 2
[0376] The light-emitting device was manufactured in essentially the same manner as in Comparative Example 1, but a premixed substrate comprising HT and ET in a 7:3 weight ratio was used instead of a single substrate to form the emission layer, and compounds 5 and 6 were used only in a 5:5 weight ratio on the hole transport layer without the use of p-dopants to form a light-emitting device with... A launch auxiliary layer of a certain thickness.
[0377]
[0378] The HOMO energy levels of compound HT1 and compounds 1 through 6 are as follows:
[0379] Compound HT1: 5.11 eV
[0380] Compound 1: 5.45 eV
[0381] Compound 2: 5.24 eV
[0382] Compound 3: 5.30 eV
[0383] Compound 4: 5.55 eV
[0384] Compound 5: 5.22 eV
[0385] Compound 6: 5.41 eV
[0386] To evaluate the characteristics of the light-emitting devices manufactured according to Comparative Examples 1 to 14, as well as Examples 1 and 2, measurements were taken at 10 mA / cm². 2 The driving voltage, efficiency, and lifespan at the given current density.
[0387] The driving voltage and current density of the light-emitting device were measured using a source meter (Keithley Instrument Company, 2400 series), and the efficiency of the light-emitting device was measured using a measuring instrument manufactured by Hamamatsu Photonics Company.
[0388] Table 1
[0389]
[0390] Referring to Table 1, it can be seen that the light-emitting devices of Examples 1 and 2 show superior results compared with the light-emitting devices of Comparative Examples 1 to 14.
[0391] According to one or more embodiments, a light-emitting device that does not contain a p-doped layer exhibits equal or better results compared to a light-emitting device that contains a p-doped layer in the emission auxiliary layer.
[0392] It should be understood that the embodiments described herein are for descriptive purposes only and not for limiting purposes. The description of features or aspects in each embodiment should generally be considered applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, those skilled in the art will understand that various changes in form and detail may be made herein without departing from the spirit and scope defined by the claims and their equivalents.
Claims
1. A light-emitting device, comprising: First electrode; The second electrode facing the first electrode; as well as An intermediate layer located between the first electrode and the second electrode and including an emission layer, the intermediate layer comprising: i) The hole transport region located between the first electrode and the emitter layer, and ii) The electron transport region located between the emitter layer and the second electrode. The hole transport region comprises two layers, each containing compound group A, compound group B, or any combination thereof. The compounds in group A comprise one or two amine groups, and the amine groups comprise a fluorene moiety, a carbazole moiety, a dibenzofuran moiety, a dibenzothiophene moiety, a dibenzothiophene moiety, or any combination thereof. The compounds in group B do not contain an amine group, but contain a fluorene moiety, a carbazole moiety, a dibenzofuran moiety, a dibenzothiophene moiety, a dibenzothiophene moiety, or any combination thereof. The two layers are a hole transport layer and an emitter assist layer, respectively, and the emitter assist layer does not contain p-dopant. The emission layer comprises two or more types of main bodies. The emission assist layer comprises assist compound 1 and assist compound 2 selected from the compound group A, the compound group B, and any combination thereof. The auxiliary compound 1 and the auxiliary compound 2 are either compound 1 and compound 2 or compound 5 and compound 6 respectively: 。 2. The light-emitting device as claimed in claim 1, wherein: The first electrode is the anode. The second electrode is a cathode, and The hole transport region further includes a hole injection layer, an electron blocking layer, or any combination thereof.
3. The light-emitting device as claimed in claim 1, wherein: The first electrode is the anode. The second electrode is a cathode, and The electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
4. The light-emitting device as claimed in claim 1, wherein: The hole transport layer comprises compound HTM selected from compound group A, compound group B, and any combination thereof. The compound HTM, the auxiliary compound 1, and the auxiliary compound 2 are different from each other.
5. The light-emitting device of claim 4, wherein compound HTM is one of the following compounds: 。 6. The light-emitting device of claim 1, wherein the emission auxiliary layer is in contact with the emission layer.
7. The light-emitting device of claim 1, wherein the emission auxiliary layer is in contact with the hole transport layer.
Citation Information
Patent Citations
Deck assembly
KR1020200029800A
The organic light emitting diode and manufacturing method thereof
KR1020100015029A
Organic light emitting diode display
US20160149152A1
Organic light-emitting device
US20170155049A1