Organic light-emitting devices
By using cooling dopants and sensitizers in the emission layer of the organic light emitting device, the specific attenuation time conditions are met, and the thermal exciton generation problem caused by triplet exciton accumulation is solved, and the effect of extending the life of the organic light emitting device and improving the luminous efficiency is achieved.
Patent Information
- Application Number
- CN202010255028.5
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2020-03-05
- Filing Date
- 2020-03-30
- Publication Date
- 2025-03-18
- Estimated Expiration
- 2040-03-30
AI Technical Summary
The accumulation of triplet excitons in the emitting layer of the existing organic light emitting devices leads to the generation of thermal excitons, thereby shortening the lifetime of the organic light emitting devices.
By introducing a cooling dopant and a sensitizer into the emission layer, specific attenuation time conditions are met to reduce triplet excitons in the sensitizer and promote their conversion to singlet excitons of the cooling dopant, thereby extending the lifetime of the organic light emitting device.
It effectively reduces the generation of thermal excitons, extends the life of organic light-emitting devices, and improves the color purity and luminous efficiency of light.
Smart Images

Figure CN111755612B_ABST
Abstract
Description
[0001] CROSS-REFERENCE TO RELATED APPLICATIONS
[0002] This application claims the benefit of Korean Patent Application No. 10-2019-0037245, filed on March 29, 2019, and Korean Patent Application No. 10-2020-0027986, filed on March 5, 2020, in the Korean Intellectual Property Office, the disclosures of which are incorporated herein in their entirety by reference. Technical Field
[0003] The present disclosure relates to an organic light emitting device including an emission layer including a host, a cooling dopant, and a sensitizer. Background Art
[0004] The organic light emitting device is a self-emissive device that produces a full-color image and has a wide viewing angle, a high contrast ratio, a short response time, and excellent characteristics in terms of brightness, driving voltage, and response speed compared to devices in the art.
[0005] In an example, an organic light emitting device includes an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer includes an emission layer. A hole transport region may be between the anode and the emission layer, and an electron transport region may be between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. Holes and electrons recombine in the emission layer to generate excitons. These excitons transition from an excited state to a ground state, thereby generating light. Summary of the invention
[0006] An organic light emitting device including an emission layer including a host, a cooling dopant, and a sensitizer is provided.
[0007] Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments of the disclosure.
[0008] According to an aspect of one embodiment, an organic light emitting device includes: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, wherein
[0009] The organic layer may include an emission layer;
[0010] The emissive layer may include a host, a cooling dopant, and a sensitizer, wherein
[0011] The cooling dopant and the sensitizer satisfy conditions 1 and 2, and
[0012] The sensitizer may include platinum (Pt):
[0013] <Condition 1>
[0014] T 衰减 (CD) <T 衰减 (S)
[0015] <Condition 2>
[0016] T 衰减 (CD)<1.5μs
[0017] Among them, in conditions 1 and 2,
[0018] T 衰减 (CD) is the decay time of the cooling dopant, and
[0019] T 衰减 (S) is the decay time of the sensitizer.
[0020] Another aspect provides an organic light emitting device, comprising: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, wherein
[0021] The organic layer may include an emission layer;
[0022] The emissive layer may include a host, a cooling dopant, and a sensitizer, wherein
[0023] The cooling dopant and the sensitizer satisfy conditions 1 and 2, and
[0024] The sensitizer may include a thermally activated delayed fluorescent emitter, and
[0025] Thermally activated delayed fluorescence emitters do not include metals:
[0026] <Condition 1>
[0027] T 衰减 (CD) <T 衰减 (S)
[0028] <Condition 2>
[0029] T 衰减 (CD)<1.5μs
[0030] Among them, in conditions 1 and 2,
[0031] T 衰减 (CD) is the decay time of the cooling dopant, and
[0032] T 衰减 (S) is the decay time of the sensitizer.
[0033] According to an aspect of another embodiment, an organic light emitting device includes: a first electrode; a second electrode; m emission units between the first electrode and the second electrode and including at least one emission layer; and
[0034] m-1 charge generation layers, which are between two adjacent emission units of the m emission units and include an n-type charge generation layer and a p-type charge generation layer,
[0035] m can be an integer of 2 or greater,
[0036] The maximum emission wavelength of light emitted from at least one of the m emission units may be different from the maximum emission wavelength of light emitted from at least one of the remaining emission units,
[0037] The emissive layer may include a host, a cooling dopant, and a sensitizer, wherein
[0038] The cooling dopant and the sensitizer satisfy conditions 1 and 2, and
[0039] The sensitizer may include Pt.
[0040] According to an aspect of another embodiment, an organic light emitting device includes: a first electrode; a second electrode; m emission units between the first electrode and the second electrode and including at least one emission layer; and
[0041] m-1 charge generation layers, which are between two adjacent emission units of the m emission units and include an n-type charge generation layer and a p-type charge generation layer,
[0042] m can be an integer of 2 or greater,
[0043] The maximum emission wavelength of light emitted from at least one of the m emission units may be different from the maximum emission wavelength of light emitted from at least one of the remaining emission units,
[0044] The emissive layer may include a host, a cooling dopant, and a sensitizer, wherein
[0045] The cooling dopant and the sensitizer satisfy conditions 1 and 2, and
[0046] The sensitizer may include a thermally activated delayed fluorescent emitter, and
[0047] Thermally activated delayed fluorescent emitters do not include metals.
[0048] According to an aspect of one embodiment, an organic light emitting device includes: a first electrode; a second electrode; and m emission layers between the first electrode and the second electrode, wherein
[0049] m can be an integer of 2 or greater,
[0050] The maximum emission wavelength of light emitted from at least one emission layer of the m emission layers may be different from the maximum emission wavelength of light emitted from at least one emission layer of the remaining emission layers,
[0051] The emissive layer may include a host, a cooling dopant, and a sensitizer, wherein
[0052] The cooling dopant and the sensitizer satisfy conditions 1 and 2, and
[0053] The sensitizer may include Pt.
[0054] According to an aspect of one embodiment, an organic light emitting device includes: a first electrode; a second electrode; and m emission layers between the first electrode and the second electrode, wherein
[0055] m can be an integer of 2 or greater,
[0056] The maximum emission wavelength of light emitted from at least one emission layer of the m emission layers may be different from the maximum emission wavelength of light emitted from at least one emission layer of the remaining emission layers,
[0057] The emissive layer may include a host, a cooling dopant, and a sensitizer, wherein
[0058] The cooling dopant and the sensitizer satisfy conditions 1 and 2, and
[0059] The sensitizer may include a thermally activated delayed fluorescent emitter, and
[0060] Thermally activated delayed fluorescent emitters do not include metals. BRIEF DESCRIPTION OF THE DRAWINGS
[0061] The above and other aspects, features and advantages of some embodiments of the present disclosure will become more apparent from the following description considered in conjunction with the accompanying drawings, in which:
[0062] Figure 1 A schematic cross-sectional view showing an organic light-emitting device according to one embodiment;
[0063] Figures 2A-2C Each shows a diagram schematically illustrating energy transfer in an emission layer of an organic light emitting device according to an embodiment;
[0064] Figure 3 is a schematic cross-sectional view of an organic light emitting device according to another embodiment; and
[0065] Figure 4 is a schematic cross-sectional view of an organic light-emitting device according to another embodiment;
[0066] Figure 5 is a graph of the luminance versus external quantum efficiency of the organic light emitting devices manufactured according to Example 3 and Comparative Example 3P; and
[0067] Figure 6 Graph showing relative brightness versus relative lifetime of the organic light emitting devices manufactured according to Example 3 and Comparative Example 3P. DETAILED DESCRIPTION
[0068] Embodiments will now be described in detail, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout. In this regard, the present embodiment may have different forms and should not be construed as being limited to the description set forth herein. Therefore, the following only describes the embodiments to illustrate aspects by reference to the accompanying drawings. As used herein, the term "and / or" includes any and all combinations of one or more of the related enumerated items. Expressions such as "at least one (kind)" when before or after a list of elements modify the entire list of elements and do not modify the individual elements of the list.
[0069] Figure 1 and 2A Description to 2C
[0070] Figure 1 FIG. 1 is a schematic diagram of an organic light emitting device 10 according to an embodiment. Figure 1 The structure and manufacturing method of an organic light emitting device according to an example of the present disclosure are described.
[0071] Figure 1 The organic light emitting device 10 includes a first electrode 11 , a second electrode 19 facing the first electrode 11 , and an organic layer 10A between the first electrode 11 and the second electrode 19 .
[0072] The organic layer 10A includes the emission layer 15 , the hole transport region 12 may be located between the first electrode 11 and the emission layer 15 , and the electron transport region 17 may be located between the emission layer 15 and the second electrode 19 .
[0073] A substrate may be additionally provided below the first electrode 11 or above the second electrode 19. For use as the substrate, any substrate used in an organic light-emitting device available in the art may be used, and the substrate may be a glass substrate or a transparent plastic substrate each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.
[0074] [First electrode 11]
[0075] In one or more embodiments, the first electrode 11 may be formed by depositing or sputtering a material for forming the first electrode 11 on a substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may be selected from materials having a high work function to facilitate hole injection.
[0076] The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 11 is a transmissive electrode, the material used to form the first electrode may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), and any combination thereof, but the embodiments of the present disclosure are not limited thereto. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the material used to form the first electrode may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof, but the embodiments of the present disclosure are not limited thereto.
[0077] The first electrode 11 may have a single-layer structure or a multi-layer structure including two or more layers.
[0078] [Emission layer 15]
[0079] The emission layer 15 may include a host, a cooling dopant, and a sensitizer.
[0080] The emission layer can emit fluorescence. That is, the cooling dopant can be a material that can emit fluorescence. The emission layer 15 that emits fluorescence is clearly distinguished from the emission layer in the related art that emits phosphorescence.
[0081] In an embodiment, the emission layer may include a host, a cooling dopant, and a sensitizer,
[0082] The cooling dopant and the sensitizer satisfy conditions 1 and 2, and
[0083] The sensitizer may include Pt:
[0084] <Condition 1>
[0085] T 衰减 (CD) <T 衰减 (S)
[0086] <Condition 2>
[0087] T 衰减 (CD)<1.5μs
[0088] Among them, in conditions 1 and 2,
[0089] T 衰减(CD) is the decay time of the cooling dopant, and
[0090] T 衰减 (S) is the decay time of the sensitizer.
[0091] The decay time of the cooling dopant was calculated from the time-resolved photoluminescence spectrum (TRPL) at room temperature for a 40 nm thick film (hereinafter referred to as "film (CD)") obtained by: -7 The host and the dopant included in the emission layer were vacuum co-deposited on a quartz substrate at a weight ratio of 90:10 under a vacuum degree of 1000 torr.
[0092] The decay time of the sensitizer was calculated with respect to the TRPL at room temperature of a 40 nm thick film (hereinafter referred to as “film (S)”) obtained as follows: -7 The host and the sensitizer included in the emission layer were vacuum co-deposited on a quartz substrate at a weight ratio of 90:10 under a vacuum degree of 1000 torr.
[0093] The detailed evaluation method of each of the decay time of the cooling dopant and the sensitizer may be understood by referring to the following examples.
[0094] Generally, it is known that since triplet excitons remain in an excited state for a long time, they have an impact on the reduction of the life span of an organic light-emitting device. However, according to the present disclosure, a cooling dopant is used to reduce the time that the triplet excitons of a sensitizer remain in an excited state. Therefore, an organic light-emitting device including the cooling dopant can have an extended life span.
[0095] In one embodiment, the more triplet excitons a sensitizer has, the more excess energy accumulated in the sensitizer, resulting in more hot excitons. That is, the amount of triplet excitons of the sensitizer is proportional to the amount of hot excitons. The hot excitons destroy various chemical bonds of the compounds included in the emission layer and / or the compounds present at the interface between the emission layer and other layers to degrade the compounds. Therefore, the lifespan of the organic light-emitting device may be reduced. However, according to the present disclosure, by using a cooling dopant, the triplet excitons of the sensitizer can be quickly converted into singlet excitons of the cooling dopant, ultimately reducing the amount of hot excitons and increasing the lifespan of the organic light-emitting device.
[0096] In this regard, "hot excitons" may be generated or increased by exciton-exciton annihilation due to an increase in the density of excitons in the emission layer, exciton-charge annihilation due to charge imbalance in the emission layer, and / or radical ion pairs due to the transport of electrons between the host and the dopant.
[0097] In order to quickly convert triplet excitons of the sensitizer into singlet excitons of the cooling dopant, condition 1 should be satisfied.
[0098] In addition, since the cooling dopant emits fluorescence, a high color purity organic light-emitting device can be provided, and in particular, since condition 2 is satisfied, the singlet excitons of the cooling dopant in an excited state at room temperature can be quickly transformed (transferred), and therefore, the singlet excitons of the cooling dopant in an excited state may not accumulate, and the lifespan of the organic light-emitting device may be increased.
[0099] In addition, when condition 3 is further satisfied, the transition (transition) from the triplet exciton of the sensitizer to the singlet exciton of the cooling dopant can occur more smoothly. Therefore, the lifetime of the organic light-emitting device can be further extended:
[0100] <Condition 3>
[0101] T 衰减 (CD) / T 衰减 (S)<0.5
[0102] Among them, in condition 3,
[0103] T 衰减 (CD) is the decay time of the cooling dopant, and
[0104] T 衰减 (S) is the decay time of the sensitizer.
[0105] In one or more embodiments, the organic light-emitting device may further satisfy condition 4:
[0106] <Condition 4>
[0107] BDE(S)–T 1 (S)<3.0eV
[0108] Among them, in condition 4,
[0109] BDE(S) is the bond dissociation (dissociation) energy level of the sensitizer, and
[0110] T 1 (S) is the lowest excited triplet energy level of the sensitizer.
[0111] Finally, the organic light emitting device can have a target lifetime level by satisfying the following condition 5:
[0112] <Condition 5>
[0113] R(Hex) / e 10 <15
[0114] Among them, in condition 5,
[0115] R(Hex) is the rate of generation of thermal excitons.
[0116] In this regard, R(Hex) is subject to the photochemical stability (photochemical stability) of the organic light emitting device and is then calculated according to the following Equation C by Gaussian 09 program.
[0117] <Equation C>
[0118] R(Hex)=a×T 衰减 (S)×e -(BDE(S)–T 1 (S))
[0119] Where, in equation C,
[0120] a is an arbitrary constant,
[0121] T 衰减 (S) is the decay time of the sensitizer,
[0122] BDE(S) is the bond dissociation energy level of the sensitizer, and
[0123] T 1 (S) is the lowest excited triplet energy level of the sensitizer.
[0124] Estimate the rate of hot exciton generation and (decay time)×e -(BDE-T1) In order to obtain the target lifetime level of the organic light-emitting device, (hot exciton generation rate) / e 10 Should be less than 15.
[0125] In this regard, the degradation analysis (PCS) of the organic light emitting device is calculated according to the following equation P:
[0126] <Equation P>
[0127] PCS(%)=I 2 / I 1 ×100
[0128] Where, in equation P,
[0129] Regarding the I of the film formed by depositing the compound whose PCS is to be measured 1 is the maximum light intensity obtained from the following PL spectrum: The PL spectrum was obtained by using a He-Cd laser (excitation wavelength = 325 nm, laser power density = 100 mW / cm 2 ) evaluated at room temperature immediately after formation of the film in an Ar atmosphere in which the outside air is blocked, and
[0130] Regarding the I of the film formed by depositing the compound whose PCS is to be measured 2 is the maximum light intensity obtained from the following PL spectrum: The PL spectrum was obtained by exposing the film to the same 1 The pump laser was a He-Cd laser from KIMMON-KOHA Inc. (excitation wavelength = 325 nm and laser power density = 100 mW / cm 2 ) light for 3 hours, and then evaluated at room temperature in an Ar atmosphere where the outside air was blocked using a He-Cd laser (excitation wavelength = 325 nm) from KIMMON-KOHA Inc. In the case of the sensitizer, reverse intersystem crossing (RISC) and / or intersystem crossing (ISC) actively occurs, which allows excitons generated at the host to be transported to the cooling dopant.
[0131] In particular, reference will be made to Figure 2A General energy transfer of the organic light emitting device according to the embodiment is described.
[0132] Singlet and triplet excitons are formed at the host in the emission layer, and the energy of the singlet and triplet excitons formed at the host is transmitted through Energy transfer (FRET) is transferred to the sensitizer and then to the cooling dopant. At this time, in order to realize high efficiency and long life of the organic light-emitting device, the hot excitons generated in the emission layer must be controlled, which requires optimization of energy transfer.
[0133] In particular, reference will be made to Figure 2B The general energy transfer (Type I) of the organic light emitting device according to the embodiment is described. This is when the sensitizer satisfies ΔE ST ≤0.3eV for thermally activated delayed fluorescence (TADF) emitters.
[0134] The energy of singlet excitons formed at the host (which is 25% of all excitons) is transferred to the sensitizer through FRET, and the energy of triplet excitons formed at the host (which is 75% of all excitons) is transferred to the singlet and triplet states of the sensitizer, where the energy transferred to the triplet state undergoes RISC into the singlet state, and then the singlet energy of the sensitizer is transferred to the cooling dopant through FRET.
[0135] In particular, reference will be made to Figure 2C A general energy transfer (Type II) of an organic light emitting device according to an embodiment is described. In this case, the sensitizer is an organic metal compound including Pt.
[0136] The energy of triplet excitons formed at the host (which is 75% of all excitons) is transferred to the sensitizer through Dexter energy transfer, and the energy of singlet excitons formed at the host (which is 25% of all excitons) is transferred to the singlet and triplet states of the sensitizer, where the energy transferred to the singlet state undergoes ISC into the triplet state, and then the triplet energy of the sensitizer is transferred to the cooling dopant through FRET.
[0137] Therefore, by transferring all singlet excitons and triplet excitons generated in the emission layer to the dopant, an organic light emitting device with improved efficiency can be obtained. In addition, since an organic light emitting device can be obtained with significantly reduced energy loss, the lifespan characteristics of the organic light emitting device can be improved.
[0138] The amount of the sensitizer in the emission layer may be about 5 wt % to about 50 wt %, based on the total weight of the emission layer. Within these ranges, efficient energy transfer in the emission layer can be achieved, and therefore, an organic light-emitting device with high efficiency and long life can be obtained.
[0139] In one embodiment, the host, cooling dopant and sensitizer may further satisfy condition 6:
[0140] <Condition 6>
[0141] T 1 (H)≥T 1 (S)≥S 1 (CD)
[0142] Among them, in condition 6,
[0143] T 1 (H) is the lowest excited triplet energy level of the host,
[0144] S 1 (CD) is the lowest excited singlet energy level of the cooling dopant, and
[0145] T 1 (S) is the lowest excited triplet energy level of the sensitizer.
[0146] When the host, the cooling dopant, and the sensitizer each satisfy Condition 6, triplet excitons may be efficiently transferred from the host to the cooling dopant, and thus, an organic light-emitting device with improved efficiency may be obtained.
[0147] The emission layer may be composed of the host, the cooling dopant, and the sensitizer. That is, the emission layer may not further include materials other than the host, the cooling dopant, and the sensitizer.
[0148] The thickness of the emission layer may be about about For example, about about When the thickness of the emission layer is within this range, excellent light emitting characteristics can be obtained without a significant increase in driving voltage.
[0149] [Main body in emission layer 15]
[0150] The host may not include metal atoms.
[0151] In one or more embodiments, the host may include one host. When the host includes one host, the one host may be selected from an amphoteric host, an electron transport host, and a hole transport host to be described later.
[0152] In one or more embodiments, the host may include a mixture of two or more different hosts. For example, the host may be a mixture of an electron transport host and a hole transport host, a mixture of two different types of electron transport hosts, or a mixture of two different types of hole transport hosts. The electron transport host and the hole transport host can be understood by referring to the relevant description to be presented later.
[0153] In one or more embodiments, the host may include an electron transporting host including at least one electron transporting moiety and a hole transporting host without an electron transporting moiety.
[0154] The electron transport moiety used herein may be selected from a cyano group, a cyclic group containing π-electron-deficient nitrogen, and a group represented by one of the following formulae:
[0155]
[0156] In the formula, *, *' and *" are each a binding site to an adjacent atom.
[0157] In one or more embodiments, the electron transport host of the emission layer 15 may include at least one of a cyano group and a cyclic group containing π-electron-deficient nitrogen.
[0158] In one or more embodiments, the electron transport host in the emission layer 15 may include at least one cyano group.
[0159] In one or more embodiments, the electron transport host in the emission layer 15 may include at least one cyano group and at least one cyclic group containing π-electron-deficient nitrogen.
[0160] In one or more embodiments, the host may include an electron transport host and a hole transport host, wherein the electron transport host may include at least one cyclic group that does not contain π-electron-deficient nitrogen and at least one electron transport portion, and the hole transport host may include at least one cyclic group that does not contain π-electron-deficient nitrogen and may not include an electron transport portion.
[0161] The term "cyclic group containing π-electron-deficient nitrogen" as used herein refers to a cyclic group having at least one *-N=*' portion, and for example, can be selected from an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, Azole group, iso azole group, pyridine group, pyrazine group, pyridazine group, pyrimidine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cinnoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzimidazole group, isobenzothiazole group, benzo Azole group, isobenzo Azole group, triazole group, tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group; and a condensed ring group of two or more π-electron-deficient nitrogen-containing cyclic groups.
[0162] At the same time, the cyclic group not containing π-electron-deficient nitrogen can be selected from a phenyl group, a heptadene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthene group, a phenanthene group, an anthracene group, a fluoranthene group, a benzo[9,10]phenanthrenene group, a pyrene group, Group, tetraphenyl group, group, a perylene group, a pentacene group, a hexacenyl group, a pentaphene group, a rubine group, a coronene group, an ovalenyl group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolecarbazole group, a benzofuranocarbazole group, a benzothiophenocarbazole group, a triindolephenyl group; and a fused ring group of two or more cyclic groups not containing π-electron-deficient nitrogen, but the embodiments of the present disclosure are not limited thereto.
[0163] In one or more embodiments, the electron transport host may be selected from a compound represented by formula E-1, and
[0164] The hole transport host may be selected from a compound represented by the formula H-1, but the embodiments of the present disclosure are not limited thereto:
[0165] <Formula E-1>
[0166] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21
[0167] Wherein, in formula E-1,
[0168] Ar 301 Can be selected from substituted or unsubstituted C 5 -C 60 Carbocyclic groups and substituted or unsubstituted C 1 -C 60 Heterocyclic groups,
[0169] xb11 can be 1, 2 or 3,
[0170] L 301 may be independently selected from a single bond, a group represented by the following formula, a substituted or unsubstituted C 5 -C 60 Carbocyclic groups, and substituted or unsubstituted C 1 -C 60 A heterocyclic group, and *, *' and *" in the following formula are each a binding site to an adjacent atom,
[0171]
[0172] xb1 can be an integer from 1 to 5.
[0173] R 301 can be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -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 )、-S(=O)(Q 301 )、-P(=O)(Q 301 )(Q 302 ), and -P(=S)(Q 301 )(Q 302 ),
[0174] xb21 can be an integer from 1 to 5.
[0175] Q 301 -Q 303 Each independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl, and
[0176] At least one of <Condition A> to <Condition C> is met:
[0177] <Condition A>
[0178] Ar in Formula E-1 301 , L 301 and R 301 Each may independently include a cyclic group containing π-electron-deficient nitrogen.
[0179] <Condition B>
[0180] L in Formula E-1 301 is a group represented by the following formula:
[0181]
[0182] <Condition C>
[0183] R in Formula E-1 301 Can be selected from cyano, -S(=O) 2 (Q 301 )、-S(=O)(Q 301 )、-P(=O)(Q 301 )(Q 302 ), and -P(=S)(Q 301 )(Q 302 ).
[0184] <Formula H-1>
[0185] Ar 401 -(L 401 ) xd1 -(Ar 402 ) xd11
[0186]
[0187] Wherein, in formulas H-1, 11 and 12,
[0188] L 401 You can choose from:
[0189] Single bond; and
[0190] each being unsubstituted or substituted with at least one substituted phenyl group, heptalene group, indene group, naphthyl group, azulene group, indacene group, acenaphthene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, Group, tetraphenyl group, group, perylene group, pentacene group, hexacenyl group, pentaphene group, rubine group, coronene group, ovobenzene group, pyrrole group, isoindole group, indole group, furan group, thiophene group, benzofuran group, benzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzofuran group, dibenzothiophene group, dibenzothiophene sulfone group, carbazole group, dibenzosilole group, indenocarbazole group, indolocarbazole group, benzofuranocarbazole group, benzothiophenocarbazole group, and triindolophenyl group: deuterium, C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzo[9,10]phenanthryl, biphenyl, terphenyl, quaterphenyl, and -Si(Q 401 )(Q402 )(Q 403 );
[0191] xd1 may be an integer of 1-10, wherein when xd1 is 2 or greater, two or more L 401 may be the same or different from each other,
[0192] xd11 may be an integer of 1-10, wherein when xd11 is 2 or greater, two or more Ar 402 may be the same or different from each other,
[0193] Ar 401 The groups represented by free formulas 11 and 12 may be selected,
[0194] Ar 402 You can choose from:
[0195] groups represented by Formulae 11 and 12, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, and a benzo[9,10]phenanthryl group; and
[0196] phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, biphenyl, terphenyl, and benzo[9,10]phenanthryl, each of which is selected from at least one substituted group consisting of deuterium, hydroxyl, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, biphenyl, terphenyl, and benzo[9,10]phenanthryl;
[0197] CY 401 and CY 402 may be each independently selected from a benzene group, a naphthalene group, a fluorene group, a carbazole group, a benzocarbazole group, an indolocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, a benzonaphthofuran group, a benzonaphthothiophene group, and a benzonaphthosilole group,
[0198] A 21 Selected from single bond, O, S, N(R 51 )、C(R 51 )(R 52 ), and Si(R 51 )(R 52 ),
[0199] A 22 Selected from single bond, O, S, N(R 53 )、C(R 53 )(R54 ), and Si(R 53 )(R 54 ),
[0200] A selected from formula 12 21 and A 2 At least one of is not a single bond,
[0201] R 51 -R 54 , R 60 and R 70 Each independently selected from:
[0202] hydrogen, deuterium, hydroxyl, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, and C 1 -C 20 Alkoxy;
[0203] Each of the following is substituted by at least one C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy: deuterium, hydroxyl, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl;
[0204] Cyclic groups that do not contain π-electron-deficient nitrogen (e.g., phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, biphenyl, terphenyl, and benzo[9,10]phenanthryl);
[0205] The cyclic groups not containing π-electron-deficient nitrogen (e.g., phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, biphenyl, terphenyl, and benzo[9,10]phenanthryl) each substituted with at least one selected from the group consisting of deuterium, hydroxyl, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothienyl, and biphenyl; and
[0206] -Si(Q 404 )(Q 405 )(Q 406 ),
[0207] e1 and e2 can each independently be an integer of 0-10,
[0208] Q 401 -Q 406 may be each independently selected from hydrogen, deuterium, hydroxyl, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, biphenyl, terphenyl, and benzo[9,10]phenanthryl, and
[0209] *Indicates the binding site with the adjacent atom.
[0210] In one or more embodiments, Ar in Formula E-1 301 and L 301 Each of the following may be independently selected from a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthene group, a phenanthene group, an anthracene group, a fluoranthene group, a benzo[9,10]phenanthrene group, a pyrene group, Group, tetraphenyl group, group, perylene group, pentaphene group, indenoanthracene group, dibenzofuran group, dibenzothiophene group, imidazole group, pyrazole group, thiazole group, isothiazole group, Azole group, iso azole group, pyridine group, pyrazine group, pyridazine group, pyrimidine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cinnoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzimidazole group, isobenzothiazole group, benzo Azole group, isobenzo Azole group, triazole group, tetrazole group, Oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group, and azacarbazole group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20alkoxy, phenyl, biphenyl, terphenyl, naphthyl, phenyl containing cyano group, biphenyl containing cyano group, terphenyl containing cyano group, naphthyl containing cyano group, pyridyl, phenylpyridyl, diphenylpyridyl, biphenylpyridyl, di(biphenyl)pyridyl, pyrazinyl, phenylpyrazinyl, diphenylpyrazinyl, biphenylpyrazinyl, di(biphenyl)pyrazinyl, pyridazinyl, phenylpyridazinyl, diphenylpyridazinyl, biphenylpyridazinyl, di(biphenyl)pyridazinyl, pyrimidinyl, phenylpyrimidinyl, diphenylpyrimidinyl, biphenylpyrimidinyl, di(biphenyl)pyrimidinyl, triazinyl, phenyltriazinyl, diphenyltriazinyl, biphenyltriazinyl, di(biphenyl)triazinyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ), and -P(=O)(Q 31 )(Q 32 ),
[0211] Quantity xb1 L 301 At least one of the following may be independently selected from imidazole groups, pyrazole groups, thiazole groups, isothiazole groups, Azole group, iso azole group, pyridine group, pyrazine group, pyridazine group, pyrimidine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cinnoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzimidazole group, isobenzothiazole group, benzo Azole group, isobenzo Azole group, triazole group, tetrazole group, Oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group, and azacarbazole group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20alkoxy, phenyl, biphenyl, terphenyl, naphthyl, phenyl containing cyano group, biphenyl containing cyano group, terphenyl containing cyano group, naphthyl containing cyano group, pyridyl, phenylpyridyl, diphenylpyridyl, biphenylpyridyl, di(biphenyl)pyridyl, pyrazinyl, phenylpyrazinyl, diphenylpyrazinyl, biphenylpyrazinyl, di(biphenyl)pyrazinyl, pyridazinyl, phenylpyridazinyl, diphenylpyridazinyl, biphenylpyridazinyl, di(biphenyl)pyridazinyl, pyrimidinyl, phenylpyrimidinyl, diphenylpyrimidinyl, biphenylpyrimidinyl, di(biphenyl)pyrimidinyl, triazinyl, phenyltriazinyl, diphenyltriazinyl, biphenyltriazinyl, di(biphenyl)triazinyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ), and -P(=O)(Q 31 )(Q 32 ),and
[0212] R 301 can be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenyl containing cyano, biphenyl containing cyano, terphenyl containing cyano, quaterphenyl containing cyano, naphthyl containing cyano, pyridyl, phenylpyridyl, diphenylpyridyl, biphenylpyridyl, di(biphenyl)pyridyl, pyrazinyl, phenylpyrazinyl, diphenylpyrazinyl, biphenylpyrazinyl, di(biphenyl)pyrazinyl, pyridazinyl, phenylpyridazinyl, diphenylpyridazinyl, biphenylpyridazinyl, di(biphenyl)pyridazinyl, pyrimidinyl, phenylpyrimidinyl, diphenylpyrimidinyl, biphenylpyrimidinyl, di(biphenyl)pyrimidinyl, triazinyl, phenyltriazinyl, diphenyltriazinyl, biphenyltriazinyl, di(biphenyl)triazinyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q31 ), and -P(=O)(Q 31 )(Q 32 ),
[0213] Where Q 31 -Q 33 Can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 An alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but the embodiments of the present disclosure are not limited thereto.
[0214] In one or more embodiments,
[0215] Ar 301 can be selected from a phenyl group, a naphthyl group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthene group, a phenanthene group, an anthracene group, a fluoranthene group, a benzo[9,10]phenanthrene group, a pyrene group, each of which is unsubstituted or substituted with at least one selected from the following Group, tetraphenyl group, group, perylene group, pentaphene group, indenoanthracene group, dibenzofuran group, and dibenzothiophene group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, phenyl, biphenyl, terphenyl, naphthyl, phenyl containing cyano group, biphenyl containing cyano group, terphenyl containing cyano group, naphthyl containing cyano group, pyridyl, phenylpyridyl, diphenylpyridyl, biphenylpyridyl, di(biphenyl)pyridyl, pyrazinyl, phenylpyrazinyl, diphenylpyrazinyl, biphenylpyrazinyl, di(biphenyl)pyrazinyl, pyridazinyl, phenylpyridazinyl, diphenylpyridazinyl, biphenylpyridazinyl, di(biphenyl)pyridazinyl, pyrimidinyl, phenylpyrimidinyl, diphenylpyrimidinyl, biphenylpyrimidinyl, di(biphenyl)pyrimidinyl, triazinyl, phenyltriazinyl, diphenyltriazinyl, biphenyltriazinyl, di(biphenyl)triazinyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ), and -P(=O)(Q 31 )(Q 32 );and
[0216] The groups represented by formulae 5-1 to 5-3 and 6-1 to 6-33, and
[0217] L 301 The groups represented by free formulae 5-1 to 5-3 and formulae 6-1 to 6-33 may be selected:
[0218]
[0219]
[0220] Among them, in formulas 5-1 to 5-3 and 6-1 to 6-33,
[0221] Z 1 can be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, phenyl, biphenyl, terphenyl, naphthyl, phenyl containing cyano group, biphenyl containing cyano group, terphenyl containing cyano group, naphthyl containing cyano group, pyridyl, phenylpyridyl, diphenylpyridyl, biphenylpyridyl, di(biphenyl)pyridyl, pyrazinyl, phenylpyrazinyl, diphenylpyrazinyl, biphenylpyrazinyl, di(biphenyl)pyrazinyl, pyridazinyl, phenylpyridazinyl, diphenylpyridazinyl, biphenylpyridazinyl, di(biphenyl)pyridazinyl, pyrimidinyl, phenylpyrimidinyl, diphenylpyrimidinyl, biphenylpyrimidinyl, di(biphenyl)pyrimidinyl, triazinyl, phenyltriazinyl, diphenyltriazinyl, biphenyltriazinyl, di(biphenyl)triazinyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ), and -P(=O)(Q 31 )(Q 32 ),
[0222] d4 can be 0, 1, 2, 3 or 4,
[0223] d3 can be 0, 1, 2 or 3,
[0224] d2 can be 0, 1, or 2, and
[0225] * and *' each represent a binding site with an adjacent atom.
[0226] Q 31 -Q 33 Same as described in this manual.
[0227] In one or more embodiments, L 301 The groups represented by the free formulas 5-2, 5-3 and 6-8 to 6-33 may be selected.
[0228] In one or more embodiments, R 301 can be selected from cyano and groups represented by formulae 7-1 to 7-18, and the number of Ar 402 At least one of the groups may be selected from the group represented by the formulae 7-1 to 7-18, but the embodiments of the present disclosure are not limited thereto:
[0229]
[0230] Among them, in formulas 7-1 to 7-18,
[0231] xb41-xb44 can each be 0, 1 or 2, wherein xb41 in formula 7-10 is not 0, the sum of xb41 and xb42 in formulas 7-11 to 7-13 is not 0, the sum of xb41, xb42 and xb43 in formulas 7-14 to 7-16 is not 0, the sum of xb41, xb42, xb43 and xb44 in formulas 7-17 and 7-18 is not 0, and * represents the binding site with the adjacent atom.
[0232] Two or more Ar in Formula E-1 301 may be the same or different from each other, two or more L 301 The two or more L in formula H-1 may be the same as or different from each other. 401 may be the same as or different from each other, and two or more Ar in formula H-1 402 Can be the same as or different from each other.
[0233] In one embodiment, the electron transport host includes i) at least one of a cyano group, a pyrimidine group, a pyrazine group, and a triazine group and ii) a benzo[9,10]phenanthrene group, and the hole transport host may include a carbazole group.
[0234] In one or more embodiments, the electron transport host may include at least one cyano group.
[0235] The electron transport host may be, for example, selected from the group HE1 to HE7, but the embodiments of the present disclosure are not limited thereto:
[0236] <Group HE1>
[0237]
[0238]
[0239]
[0240]
[0241]
[0242]
[0243]
[0244]
[0245]
[0246]
[0247]
[0248]
[0249]
[0250]
[0251]
[0252]
[0253]
[0254]
[0255]
[0256]
[0257]
[0258]
[0259]
[0260] <Group HE2>
[0261]
[0262]
[0263]
[0264]
[0265]
[0266]
[0267]
[0268]
[0269]
[0270]
[0271]
[0272]
[0273]
[0274]
[0275]
[0276]
[0277]
[0278]
[0279]
[0280]
[0281]
[0282]
[0283]
[0284]
[0285]
[0286]
[0287]
[0288]
[0289]
[0290]
[0291]
[0292]
[0293]
[0294]
[0295] <Group HE3>
[0296]
[0297]
[0298]
[0299]
[0300]
[0301]
[0302]
[0303]
[0304]
[0305]
[0306]
[0307]
[0308]
[0309]
[0310]
[0311]
[0312]
[0313]
[0314]
[0315]
[0316]
[0317] <Group HE4>
[0318]
[0319]
[0320]
[0321]
[0322]
[0323]
[0324]
[0325] <Group HE5>
[0326]
[0327]
[0328]
[0329]
[0330]
[0331]
[0332] <Group HE6>
[0333]
[0334]
[0335]
[0336]
[0337]
[0338]
[0339]
[0340]
[0341]
[0342] <Group HE7>
[0343]
[0344]
[0345]
[0346]
[0347]
[0348]
[0349]
[0350] In one embodiment, the hole transport host may be selected from compounds H-H1 to H-H103, but the embodiments of the present disclosure are not limited thereto:
[0351]
[0352]
[0353]
[0354]
[0355]
[0356]
[0357] In one embodiment, the amphiphilic subject may be selected from group HEH1, but the embodiments of the present disclosure are not limited thereto:
[0358] <Group HEH1>
[0359]
[0360]
[0361]
[0362]
[0363]
[0364]
[0365]
[0366]
[0367]
[0368]
[0369]
[0370]
[0371]
[0372]
[0373] Among them, in compounds 1 to 432,
[0374] Ph may be phenyl.
[0375] When the host is a mixture of an electron transport host and a hole transport host, the weight ratio of the electron transport host to the hole transport host may be 1:9 to 9:1, for example, 2:8 to 8:2, for example, 4:6 to 6:4, for example, 5:5. When the weight ratio of the electron transport host to the hole transport host satisfies the above range, a hole and electron transport balance in the emission layer 15 can be achieved.
[0376] [Cooling Dopant in Emitting Layer 15]
[0377] Since the cooling dopant emits fluorescence, the organic light-emitting device according to an embodiment of the present disclosure is clearly distinguished from an organic light-emitting device containing a compound that emits phosphorescence.
[0378] As described above, the cooling dopant satisfies condition 2.
[0379] The maximum emission wavelength of the emission spectrum of the cooling dopant may be 400 nm or more and 550 nm or less. For example, the maximum emission wavelength of the emission spectrum of the cooling dopant may be 400 nm or more and 495 nm or less, or 450 nm or more and 495 nm or less, but the embodiments of the present disclosure are not limited thereto. In other words, the cooling dopant may emit blue light. The "maximum emission wavelength" refers to the wavelength at which the emission intensity is the greatest, and may also be referred to as the "peak emission wavelength".
[0380] In an embodiment, the cooling dopant may not include metal atoms.
[0381] In an embodiment, the cooling dopant may be selected from condensed polycyclic compounds and styrene-based compounds.
[0382] For example, the cooling dopant may include a naphthalene-containing core, a fluorene-containing core, a spiro-bifluorene-containing core, a benzofluorene-containing core, a dibenzofluorene-containing core, a phenanthrene-containing core, an anthracene-containing core, a fluoranthene-containing core, a benzo[9,10]phenanthrene-containing core, a pyrene-containing core, a The core of tetracene, the core of A core containing perylene, a core containing pentaphene, a core containing indenoanthracene, a core containing bianthracene, and one of the cores represented by 501-1 to 501-18, but the embodiments of the present disclosure are not limited thereto:
[0383]
[0384]
[0385] In one or more embodiments, the cooling dopant may be selected from a styrylamine-based compound and a styrylcarbazole-based compound, but embodiments of the present disclosure are not limited thereto.
[0386] In one embodiment, the cooling dopant may be selected from a compound represented by formula 501:
[0387] <Formula 501>
[0388]
[0389] In formula 501,
[0390] Ar 501 You can choose from:
[0391] Naphthalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenanthrene group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, Group, tetraphenyl group, group, a perylene group, a pentaphene group, an indenoanthracene group, a bianthracene group, and groups represented by Formulae 501-1 to 501-18; and
[0392] Each is selected from at least one substituted naphthyl group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenanthrene group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, Group, tetraphenyl group, A group, a perylene group, a pentaphene group, an indenoanthracene group, a bianthracene group, and a group represented by the formulae 501-1 to 501-18: deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidine group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group and -Si(Q 501 )(Q 502 )(Q 503 )(where Q 501 -Q 503 can be independently selected from hydrogen, C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, C 6 -C 60 Aryl, C 1 -C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heteropolycyclic group);
[0393] L 501 -L 503 may be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0394] R 501 -R 508 Can be independently selected from:
[0395] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, yl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazole, triazine, dibenzofuranyl, and dibenzothiophenyl; and
[0396] Each of which is selected from at least one substituted phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, yl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, triazinyl, dibenzofuranyl, and dibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, yl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, triazinyl, dibenzofuranyl, and dibenzothiophenyl,
[0397] xd1-xd3 may each independently be selected from 0, 1, 2 and 3, and
[0398] xd4 can be selected from 0, 1, 2, 3, 4, 5 and 6.
[0399] For example, in Equation 501,
[0400] Ar 501 You can choose from:
[0401] Naphthalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenanthrene group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, Group, tetraphenyl group, group, a perylene group, a pentaphene group, an indenoanthracene group, a bianthracene group, and groups represented by Formulae 501-1 to 501-18; and
[0402] Each is selected from at least one substituted naphthyl group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenanthrene group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, Group, tetraphenyl group, A group, a perylene group, a pentaphene group, an indenoanthracene group, a bianthracene group, and a group represented by the formulae 501-1 to 501-18: deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidine group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, pyridyl, pyrimidinyl, triazine, quinolyl, isoquinolyl and -Si(Q 501 )(Q 502 )(Q 503 )(Q 501 -Q 503 can be independently selected from hydrogen, C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, phenyl, biphenyl, terphenyl, and naphthyl),
[0403] xd1-xd3 may each be independently selected from 0, 1 and 2, and
[0404] xd4 may be selected from 0, 1, 2, and 3, but the embodiments of the present disclosure are not limited thereto.
[0405] In one or more embodiments, the cooling dopant may include a compound represented by one of Formulas 502-1 to 502-5:
[0406] <Formula 502-1>
[0407]
[0408] <Formula 502-2>
[0409]
[0410] <Formula 502-3>
[0411]
[0412] <Formula 502-4>
[0413]
[0414] <Formula 502-5>
[0415]
[0416] Among them, in formulas 502-1 to 502-5,
[0417] X 51 Can be N or C-[(L 501 ) xd1 -R 501 ], X 52 Can be N or C-[(L 502 ) xd2 -R 502 ], X 53 Can be N or C-[(L 503 ) xd3 -R 503 ], X 54 Can be N or C-[(L 504 ) xd4 -R 504 ], X 55 Can be N or C-[(L 505 ) xd5 -R 505 ], X 56 Can be N or C-[(L 506 ) xd6 -R 506 ], X 57 Can be N or C-[(L 507 ) xd7 -R 507 ], and X 58 Can be N or C-[(L 508 ) xd8 -R 508 ],
[0418] L 501 -L 508 Each of them is related to L in formula 501 501 Same as described,
[0419] xd1-xd8 are each the same as described with respect to xd1 in Formula 501,
[0420] R 501 -R 508 Can be independently selected from:
[0421] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy,
[0422] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, yl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazole, triazine, dibenzofuranyl, and dibenzothiophenyl; and
[0423] Each of which is selected from at least one substituted phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, yl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, triazinyl, dibenzofuranyl, and dibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, yl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, triazinyl, dibenzofuranyl, and dibenzothiophenyl,
[0424] xd11 and xd12 can each independently be an integer from 0 to 5, and
[0425] R 501 -R 504 Two of may be optionally linked together to form a saturated or unsaturated ring, and
[0426] R 505 -R 508 Two of may be optionally linked together to form a saturated or unsaturated ring.
[0427] The cooling dopant may include at least one compound selected from, for example, the following compounds FD(1) to FD(16) and FD1 to FD18:
[0428]
[0429]
[0430]
[0431]
[0432] An amount of the cooling dopant in the emission layer may be about 0.01 wt % to about 15 wt % based on the total weight of the emission layer, but embodiments of the present disclosure are not limited thereto.
[0433] [Sensitizer in Emissive Layer 15]
[0434] The sensitizer may include Pt. In one embodiment, the sensitizer may be an organic metal compound containing Pt.
[0435] In one embodiment, the sensitizer may include Pt and an organic ligand (L 11 ), and L 11 and Pt can form 1, 2, 3 or 4 cyclometalated rings.
[0436] In an embodiment, the sensitizer may include an organometallic compound represented by Formula 101:
[0437] <Formula 101>
[0438] Pt(L 11 ) n11 (L 12 ) n12
[0439] Wherein, in Formula 101,
[0440] L 11 is a ligand represented by one of formulae 1-1 to 1-4;
[0441] L 12 may be selected from monodentate ligands and bidentate ligands;
[0442] n11 can be 1,
[0443] n12 can be selected from 0, 1 and 2;
[0444]
[0445] Among them, in formulas 1-1 to 1-4,
[0446] A 1 -A 4 may be independently selected from substituted or unsubstituted C 5 -C 30 Carbocyclic group, substituted or unsubstituted C1 -C 30 Heterocyclic groups, and non-cyclic groups,
[0447] Y 11 -Y 14 Can be independently a chemical bond, O, S, N (R 91 )、B(R 91 )、P(R 91 ), or C(R 91 )(R 92 ),
[0448] T 1 -T 4 can be independently selected from a single bond, a double bond, *-N(R 93 )-*'、*-B(R 93 )-*'、*-P(R 93 )-*'、*-C(R 93 )(R 94 )-*'、*-Si(R 93 )(R 94 )-*'、*-Ge(R 93 )(R 94 )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) 2 -*'、*-C(R 93 )=*'、*=C(R 93 )-*'、*-C(R 93 )=C(R 94 )-*', *-C(=S)-*', and *-C≡C-*',
[0449] Substituted C 5 -C 30 Substituents of carbocyclic groups, substituted C 1 -C 30 The substituent of the heterocyclic group, and R 91 -R 94 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ), and -P(=S)(Q 1 )(Q 2 ), wherein the substituted C 5 -C 30 Substituents of carbocyclic groups and substituted C 1 -C 30 The substituents of the heterocyclic group are each not hydrogen,
[0450] * 1 ,* 2 ,* 3 and* 4 Each represents a binding site with Pt, and
[0451] Q 1 -Q 3 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, selected from deuterium, -F, cyano, C 1 -C 60 Alkyl, and C 6 -C 60 At least one substituted C 1 -C 60 alkyl, and is selected from deuterium, -F, cyano, C 1 -C 60 Alkyl, and C 6 -C 60 At least one substituted C 6 -C 60 Aryl.
[0452] In one or more embodiments, the sensitizer may be selected from Groups I, II, III, V and VI, but the embodiments of the present disclosure are not limited thereto:
[0453] <Group I>
[0454]
[0455] <Group II>
[0456]
[0457]
[0458]
[0459]
[0460]
[0461] <Group III>
[0462]
[0463]
[0464]
[0465]
[0466]
[0467]
[0468]
[0469]
[0470]
[0471]
[0472]
[0473]
[0474]
[0475]
[0476]
[0477]
[0478]
[0479]
[0480]
[0481]
[0482] <Group V>
[0483] A compound represented by the following formula A:
[0484] <Formula A>
[0485] (L 101 ) n101 -M 101 -(L 102 ) m101
[0486] L in formula A 101 、n101、M 101 , L 102 and m101 are the same as shown in Table 1:
[0487] Table 1
[0488]
[0489]
[0490]
[0491]
[0492] LM11, LM13, LM15, LM45, LM47, LM49, LM98, LM100, LM102, LM132, LM134, LM136, LM151, LM153, LM158, LM180, LM182, LM187, LM201, LM206, LM211, LM233, LM235, LM240, LFM5, LFM6, LFM7, LFP5, LFP6 and LFP7 in Table 1 can be understood by referring to Formulas 1-1 to 1-3 and Tables 2 to 4:
[0493]
[0494] Table 2
[0495]
[0496]
[0497] [Table 3]
[0498]
[0499] Table 4
[0500]
[0501] Y1-Y18 in Tables 2 to 4 are the same as below:
[0502]
[0503] <Group VI>
[0504]
[0505] In one or more embodiments, the sensitizer may be a thermally activated delayed fluorescent emitter. The thermally activated delayed fluorescent emitter may not include a metal. In one embodiment, the thermally activated delayed fluorescent emitter may satisfy condition 7:
[0506] <Condition 7>
[0507] ΔE ST ≤0.3eV
[0508] Among them, in condition 7,
[0509] ΔE ST is the difference between the lowest excited singlet energy level and the lowest excited triplet energy level of the sensitizer.
[0510] In one embodiment, the sensitizer may include a thermally activated delayed fluorescence emitter represented by Formula 201 or 202:
[0511]
[0512] In equations 201 and 202,
[0513] A 21 is the acceptor group,
[0514] D 21 is the donor group,
[0515] m21 may be 1, 2 or 3, and n21 may be 1, 2 or 3,
[0516] The sum of n21 and m21 in Formula 201 may be 6 or less, and the sum of n21 and m21 in Formula 202 may be 5 or less,
[0517] R 21 Can be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, SF 5 , hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkaryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ), and -P(=S)(Q 1 )(Q 2 ), multiple R 21 may be optionally linked together to form a substituted or unsubstituted C 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic groups,
[0518] Q 1-Q3 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, selected from deuterium, -F, cyano, C 1 -C 60 Alkyl, and C 6 -C 60 At least one substituted C 1 -C 60 Alkyl, and is selected from deuterium, -F, cyano, C 1 -C 60 Alkyl, and C 6 -C 60 At least one substituted C 6 -C 60 Aryl.
[0519] For example, A in equations 201 and 202 21 It may be a substituted or unsubstituted cyclic group that does not contain π-electron-deficient nitrogen.
[0520] In one embodiment, the cyclic group not containing π-electron-deficient nitrogen can be selected from a phenyl group, a heptadiene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthene group, a phenanthene group, an anthracene group, a fluoranthene group, a benzo[9,10]phenanthrene group, a pyrene group, Group, tetraphenyl group, group, a perylene group, a pentacene group, a hexacenyl group, a pentaphene group, a rubine group, a coronene group, an ovalenyl group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolecarbazole group, a benzofuranocarbazole group, a benzothiophenocarbazole group, a triindolephenyl group; and a fused ring group of two or more cyclic groups not containing π-electron-deficient nitrogen, but the embodiments of the present disclosure are not limited thereto.
[0521] For example, D in Eqs. 201 and 202 21 Can be selected from: -F, cyano, and cyclic groups containing π-electron-deficient nitrogen;
[0522] C each substituted with at least one selected from -F and cyano 1 -C 60 an alkyl group, a cyclic group containing a π-electron-deficient nitrogen, and a cyclic group not containing a π-electron-deficient nitrogen; and
[0523] Each is selected from deuterium, C 1 -C 60 At least one substituted π-electron-deficient nitrogen-containing cyclic group of an alkyl group, a π-electron-deficient nitrogen-containing cyclic group, and a π-electron-deficient nitrogen-containing cyclic group:.
[0524] In one embodiment, the cyclic group not containing π-electron-deficient nitrogen is the same as described above.
[0525] The term "cyclic group containing π-electron-deficient nitrogen" as used herein refers to a cyclic group having at least one *-N=*' portion, and for example, can be selected from an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, Azole group, iso azole group, pyridine group, pyrazine group, pyridazine group, pyrimidine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cinnoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzimidazole group, isobenzothiazole group, benzo Azole group, isobenzo Azole group, triazole group, tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, an azacarbazole group, and a benzimidazolobenzimidazole group; and a condensed ring group in which two or more cyclic groups containing π-electron-deficient nitrogen are condensed to each other.
[0526] In one or more embodiments, the sensitizer may be selected from Groups VII to XI, but the embodiments of the present disclosure are not limited thereto:
[0527] <Group VII>
[0528]
[0529]
[0530]
[0531]
[0532]
[0533] <Group VIII>
[0534]
[0535]
[0536] <Group IX>
[0537]
[0538]
[0539]
[0540]
[0541]
[0542]
[0543]
[0544]
[0545]
[0546]
[0547]
[0548]
[0549]
[0550]
[0551]
[0552]
[0553]
[0554]
[0555]
[0556]
[0557]
[0558]
[0559]
[0560]
[0561]
[0562]
[0563]
[0564]
[0565]
[0566]
[0567]
[0568]
[0569]
[0570] <Group X>
[0571]
[0572]
[0573]
[0574]
[0575]
[0576]
[0577]
[0578]
[0579]
[0580]
[0581]
[0582]
[0583]
[0584]
[0585]
[0586]
[0587]
[0588]
[0589]
[0590]
[0591]
[0592]
[0593]
[0594]
[0595]
[0596]
[0597]
[0598]
[0599]
[0600]
[0601]
[0602]
[0603]
[0604]
[0605]
[0606]
[0607]
[0608]
[0609]
[0610]
[0611]
[0612]
[0613]
[0614]
[0615]
[0616]
[0617]
[0618]
[0619]
[0620]
[0621]
[0622]
[0623]
[0624]
[0625]
[0626]
[0627]
[0628]
[0629]
[0630]
[0631]
[0632]
[0633]
[0634]
[0635]
[0636]
[0637]
[0638] <Group XI>
[0639]
[0640] [Hole transport region 12]
[0641] The hole transport region 12 may be located between the first electrode 11 and the emission layer 15 of the organic light emitting device 10 .
[0642] The hole transport region 12 may have a single-layer structure or a multi-layer structure.
[0643] For example, the hole transport region 12 may have a hole injection layer, a hole transport layer, a hole injection layer / hole transport layer structure, a hole injection layer / first hole transport layer / second hole transport layer structure, a hole transport layer / intermediate layer structure, a hole injection layer / hole transport layer / intermediate layer structure, a hole transport layer / electron blocking layer or a hole injection layer / hole transport layer / electron blocking layer structure, but the embodiments of the present disclosure are not limited thereto.
[0644] The hole transport region 12 may include any compound having hole transport properties.
[0645] For example, the hole transport region 12 may include an amine-based compound.
[0646] In one embodiment, the hole transport region 12 may include at least one selected from the group consisting of a compound represented by Formula 301 to a compound represented by Formula 305, but embodiments of the present disclosure are not limited thereto:
[0647] <Formula 301>
[0648]
[0649] <Formula 302>
[0650]
[0651] <Formula 303>
[0652]
[0653] <Formula 304>
[0654]
[0655] <Formula 305>
[0656]
[0657] Wherein, in Formulas 301 to 305,
[0658] L 201 -L 209 can be independently *-O-*', *-S-*', substituted or unsubstituted C 5 -C 60 A carbocyclic group, or a substituted or unsubstituted C 1 -C 60 Heterocyclic groups,
[0659] xa1-xa9 can each independently be an integer from 0 to 5, and
[0660] R 201 -R 206 may be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, wherein R 201 -R 206 Two adjacent groups of may optionally be linked to each other via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group.
[0661] For example,
[0662] L 201 -L 209 can be selected from a phenyl group, a heptalene group, an indene group, a naphthyl group, an azulene group, a heptalene group, an indacene group, an acenaphthene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthene group, a phenanthren group, an anthracene group, a fluoranthene group, a benzo[9,10]phenanthren group, a pyrene group, each of which is unsubstituted or substituted with at least one substituted selected from the following Group, tetraphenyl group, group, perylene group, pentacene group, hexacenyl group, pentaphene group, rubine group, coronene group, ovobenzene group, pyrrole group, isoindole group, indole group, furan group, thiophene group, benzofuran group, benzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzofuran group, dibenzothiophene group, dibenzothiophene sulfone group, carbazole group, dibenzosilole group, indenocarbazole group, indolocarbazole group, benzofuranocarbazole group, benzothiophenocarbazole group, and triindolophenyl group: deuterium, C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzo[9,10]phenanthryl, biphenyl, terphenyl, quaterphenyl, and -Si(Q 11 )(Q 12 )(Q 13 ),
[0663] xa1-xa9 can each independently be 0, 1 or 2, and
[0664] R 201 -R 206 Each of the following may be independently selected from phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1-Hydroxy, 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C 1 -C 10 Alkyl-substituted phenyl, -F-substituted phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, phenyl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, coronene, ovalene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, -Si(Q 31 )(Q 32 )(Q 33 ), and -N(Q 31 )(Q 32 ),
[0665] Where Q 11 -Q 13 and Q 31 -Q 33 Can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.
[0666] In one or more embodiments, the hole transport region 12 may include an amine-based compound including carbazole.
[0667] In one embodiment, the hole transport region 12 may include an amine-based compound containing carbazole and an amine-based compound not containing carbazole.
[0668] The amine-based compound containing carbazole may be selected from, for example, a compound represented by Formula 301 including a carbazole group and further including at least one selected from a dibenzofuran group, a dibenzothiophene group, a fluorene group, a spiro-bifluorene group, an indenocarbazole group, an indolecarbazole group, a benzofuranocarbazole group, and a benzothiophenocarbazole group.
[0669] The carbazole-free amine-based compound may be selected from, for example, a compound represented by Formula 301 that does not include a carbazole group and includes at least one selected from a dibenzofuran group, a dibenzothiophene group, a fluorene group, a spiro-bifluorene group, an indenocarbazole group, an indolecarbazole group, a benzofuranocarbazole group, and a benzothiophenocarbazole group.
[0670] In one or more embodiments, the hole transport region 12 may include at least one selected from the compounds represented by Formula 301 or 302 .
[0671] In one embodiment, the hole transport region 12 may include at least one selected from the compounds represented by Formulae 201-1, 202-1, and 201-2, but embodiments of the present disclosure are not limited thereto:
[0672] <Formula 201-1>
[0673]
[0674] <Formula 202-1>
[0675]
[0676] <Formula 201-2>
[0677]
[0678] In formulas 201-1, 202-1 and 201-2, L 201 -L 203 , L 205 ,xa1-xa3,xa5,R 201 and R 202 Same as described in this article, and R 211 -R 213 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, C 1 -C 10Alkyl-substituted phenyl, -F-substituted phenyl, naphthyl, fluorenyl, spiro-bifluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzo[9,10]phenanthryl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, and pyridyl.
[0679] For example, the hole transport region 12 may include at least one selected from compounds HT1 to HT39, but embodiments of the present disclosure are not limited thereto.
[0680]
[0681]
[0682]
[0683]
[0684] In one or more embodiments, the hole transport region 12 of the organic light emitting device 10 may further include a p-dopant. When the hole transport region 12 further includes a p-dopant, the hole transport region 12 may have a matrix (e.g., at least one of the compounds represented by Formulae 301 to 305) and a p-dopant included in the matrix. The p-dopant may be uniformly or non-uniformly doped in the hole transport region 12.
[0685] In one embodiment, the p-dopant may have a LUMO level of -3.5 eV or less.
[0686] The p-dopant may include at least one selected from a quinone derivative, a metal oxide, and a cyano group-containing compound, but embodiments of the present disclosure are not limited thereto.
[0687] In one embodiment, the p-dopant may include at least one selected from the following:
[0688] Quinone derivatives such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanobenzoquinodimethane (F4-TCNQ), and F6-TCNNQ;
[0689] Metal oxides such as tungsten oxide or molybdenum oxide;
[0690] 1,4,5,8,9,12-Hexaazabenzo[9,10]phenanthrene-hexacarbonitrile (HAT-CN); and
[0691] A compound represented by the following formula 221,
[0692] However, the implementation methods of the present disclosure are not limited thereto:
[0693]
[0694] <Formula 221>
[0695]
[0696] In formula 221,
[0697] R 221 -R 223 may be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 1 -C 60 heteroaryl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, and is selected from R 221 -R 223 At least one of the following may have at least one substituent selected from the group consisting of cyano, -F, -Cl, -Br, -I, C substituted with -F 1 -C 20 Alkyl, C substituted by -Cl 1 -C 20 Alkyl, C substituted by -Br 1 -C 20 Alkyl, and C substituted by -I 1 -C 20 alkyl.
[0698] The hole transport region 12 may have a about For example, about about The thickness of the emission layer 15 may be about about For example, about about When the thickness of each of the hole transport region 12 and the emission layer 15 is within these ranges described above, satisfactory hole transport characteristics and / or light emitting characteristics may be obtained without a significant increase in driving voltage.
[0699] [Electron transport region 17]
[0700] The electron transport region 17 is disposed between the emission layer 15 and the second electrode 19 of the organic light emitting device 10 .
[0701] The electron transport region 17 may have a single-layer structure or a multi-layer structure.
[0702] For example, the electron transport region 17 may have an electron transport layer, an electron transport layer / electron injection layer structure, a buffer layer / electron transport layer structure, a hole blocking layer / electron transport layer structure, a buffer layer / electron transport layer / electron injection layer structure, or a hole blocking layer / electron transport layer / electron injection layer structure, but the embodiments of the present disclosure are not limited thereto. The electron transport region 17 may further include an electron control layer.
[0703] The electron transport region 17 may include a known electron transport material.
[0704] The electron transport region (e.g., a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound containing at least one cyclic group containing π-electron-deficient nitrogen. The cyclic group containing π-electron-deficient nitrogen is the same as described above.
[0705] For example, the electron transport region may include a compound represented by the following Formula 601:
[0706] <Formula 601>
[0707] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21
[0708] In formula 601,
[0709] Ar 601 and L 601 may be independently substituted or unsubstituted C 5 -C 60 A carbocyclic group or a substituted or unsubstituted C 1 -C 60 Heterocyclic groups,
[0710] xe11 can be 1, 2 or 3,
[0711] xe1 can be an integer from 0 to 5.
[0712] R 601 Can be selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 601 )(Q 602 )(Q 603 )、-C(=O)(Q 601 )、-S(=O) 2 (Q 601 ), and -P(=O)(Q 601 )(Q 602 ),
[0713] Q 601 -Q 603 Can be independently C 1 -C 10 Alkyl, C 1 -C 10 alkoxy, phenyl, biphenyl, terphenyl, or naphthyl, and
[0714] xe21 can be an integer from 1 to 5.
[0715] In one embodiment, the number xe11 of Ar 601 and the number xe21 R 601 At least one of may include a cyclic group containing π-electron-deficient nitrogen.
[0716] In one embodiment, ring Ar in formula 601 601 and L 601 Each of the following may be independently selected from a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthene group, a phenanthene group, an anthracene group, a fluoranthene group, a benzo[9,10]phenanthrene group, a pyrene group, Group, tetraphenyl group, group, perylene group, pentaphene group, indenoanthracene group, dibenzofuran group, dibenzothiophene group, carbazole group, imidazole group, pyrazole group, thiazole group, isothiazole group, Azole group, iso azole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cinnoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzimidazole group, isobenzothiazole group, benzo Azole group, isobenzo Azole group, triazole group, tetrazole group, Oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group, and azacarbazole group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C20 alkyl, C1-C20 alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q) 31 )(Q 32 )(Q 33 )、-S(=O) 2 (Q 31 ), and -P(=O)(Q 31 )(Q 32 ),
[0717] Where Q 31 -Q 33 Can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.
[0718] When xe11 in Formula 601 is 2 or greater, two or more Ar 601 can be connected to each other via a single bond.
[0719] In one or more embodiments, Ar in Formula 601 601 It may be an anthracene group.
[0720] In one or more embodiments, the compound represented by Formula 601 can be represented by Formula 601-1:
[0721] <Formula 601-1>
[0722]
[0723] In formula 601-1,
[0724] X 614 Can be N or C(R 614 ), X 615 Can be N or C(R 615 ), X 616 Can be N or C(R616 ), and selected from X 614 -X 616 At least one of may be N,
[0725] L 611 -L 613 Can be independently related to L 601 Same as described,
[0726] xe611-xe613 can be independently the same as described for xe1,
[0727] R 611 -R 613 Can be independently related to R 601 Same as described, and
[0728] R 614 -R 616 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, and naphthyl.
[0729] In one or more embodiments, xe1 and xe611-xe613 in formulas 601 and 601-1 may each independently be 0, 1 or 2.
[0730] In one or more embodiments, R in Formula 601 and 601-1 601 and R 611 -R 613 Each of the following may be independently selected from phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso Azolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, imidazopyridyl, imidazopyrimidyl, and azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso Azolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzo Azolyl, isobenzo oxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and
[0731] -S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ),
[0732] Where Q 601 and Q 602 Same as described above.
[0733] The electron transport region may include at least one compound selected from compounds ET1 to ET36, but embodiments of the present disclosure are not limited thereto:
[0734]
[0735]
[0736]
[0737] In one or more embodiments, the electron transport region may include a member selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3 , BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), and at least one of NTAZ:
[0738]
[0739] The thickness of the buffer layer, the hole blocking layer and the electron control layer can be independently about about For example, about about When the thicknesses of the buffer layer, the hole blocking layer, and the electron control layer are within these ranges, excellent hole blocking characteristics or excellent electron control characteristics may be obtained without a significant increase in driving voltage.
[0740] The thickness of the electron transport layer may be about about For example, about about When the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory electron transport characteristics without a significant increase in driving voltage.
[0741] The electron transport region 17 (eg, an electron transport layer in the electron transport region) may further include a material containing a metal in addition to the materials described above.
[0742] The metal-containing material may include at least one selected from an alkali metal complex and an alkaline earth metal complex. The alkali metal complex may include a metal ion selected from Li ion, Na ion, K ion, Rb ion, and Cs ion, and the alkaline earth metal complex may include a metal ion selected from Be ion, Mg ion, Ca ion, Sr ion, and Ba ion. The ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl Azoles, hydroxyphenylthiazoles, hydroxydiphenyl oxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but embodiments of the present disclosure are not limited thereto.
[0743] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (lithium quinolate, LiQ) or ET-D2:
[0744]
[0745] The electron transport region 17 may include an electron injection layer that facilitates injection of electrons from the second electrode 19. The electron injection layer may be in direct contact with the second electrode 19.
[0746] The electron injection layer may have i) a single-layer structure including a single layer containing a single material, ii) a single-layer structure including a single layer containing a plurality of different materials, or iii) a multi-layer structure having a plurality of layers each containing a plurality of different materials.
[0747] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
[0748] The alkali metal may be selected from Li, Na, K, Rb, and Cs. In one embodiment, the alkali metal may be Li, Na, or Cs. In one or more embodiments, the alkali metal may be Li or Cs, but the embodiments of the present disclosure are not limited thereto.
[0749] The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.
[0750] The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.
[0751] The alkali metal compounds, alkaline earth metal compounds, and rare earth metal compounds may be selected from oxides and halides (e.g., fluorides, chlorides, bromides, or iodides) of the alkali metals, alkaline earth metals, and rare earth metals.
[0752] The alkali metal compounds may be selected from alkali metal oxides such as Li 2 O, Cs 2 O, or K 2 O, and alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI. In one embodiment, the alkali metal compounds may be selected from LiF, Li 2 O, NaF, LiI, NaI, CsI, and KI, but the embodiments of the present disclosure are not limited thereto.
[0753] The alkaline earth metal compounds may be selected from alkaline earth metal oxides such as BaO, SrO, CaO, Ba x Sr 1-x O (0 < x < 1), or Ba x Ca 1-x O (0 < x < 1). In one embodiment, the alkaline earth metal compounds may be selected from BaO, SrO, and CaO, but the embodiments of the present disclosure are not limited thereto.
[0754] The rare earth metal compound may be selected from YbF 3 ScF 3 ScO 3 Sc 2 O 3 , Y 2 O 3 、Ce 2 O 3 , GdF 3 , and TbF 3 In one embodiment, the rare earth metal compound may be selected from YbF 3 ScF 3 , TbF 3 ,YbI 3 ScI 3 , and TbI 3 , but the implementation of the present disclosure is not limited thereto.
[0755] The alkali metal complex, alkaline earth metal complex and rare earth metal complex may include ions of the alkali metal, alkaline earth metal and rare earth metal as described above, and the ligand coordinated with the metal ions of the alkali metal complex, alkaline earth metal complex or rare earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl Azoles, hydroxyphenylthiazoles, hydroxydiphenyl oxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but embodiments of the present disclosure are not limited thereto.
[0756] The electron injection layer may be composed of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof as described above. In one or more embodiments, the electron injection layer may further include an organic material. When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof may be uniformly or non-uniformly dispersed in a matrix including the organic material.
[0757] The thickness of the electron injection layer can be about about For example, about about When the thickness of the electron injection layer is within the range described above, the electron injection layer may have satisfactory electron injection characteristics without a significant increase in driving voltage.
[0758] [Second electrode 19]
[0759] The second electrode 19 is disposed on the organic layer 10A having such a structure. The second electrode 19 may be a cathode as an electron injection electrode, and in this regard, a material for forming the second electrode 19 may be selected from metals, alloys, conductive compounds, and combinations thereof having a relatively low work function.
[0760] The second electrode 19 may include at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ITO, and IZO, but the embodiments of the present disclosure are not limited thereto. The second electrode 19 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
[0761] The second electrode 19 may have a single-layer structure having a single layer or a multi-layer structure including two or more layers.
[0762] In the above, reference has been made to Figure 1 An organic light emitting device is described, but embodiments of the present disclosure are not limited thereto.
[0763] [ Figure 3 Description]
[0764] Figure 3 is a schematic cross-sectional view of an organic light emitting device 100 according to another embodiment.
[0765] Figure 3 The organic light emitting device 100 includes a first electrode 110, a second electrode 190 facing the first electrode 110, and a first emission unit 151 and a second emission unit 152 between the first electrode 110 and the second electrode 190. The charge generation layer 141 is located between the first emission unit 151 and the second emission unit 152, and the charge generation layer 141 may include an n-type charge generation layer 141-N and a p-type charge generation layer 141-P. The charge generation layer 141 is a layer that generates charges and supplies the charges to adjacent emission units, and any known material may be used therefor.
[0766] The first emission unit 151 may include a first emission layer 151-EM, and the second emission unit 152 may include a second emission layer 152-EM. The maximum emission wavelength of light emitted from the first emission unit 151 may be different from the maximum emission wavelength of light emitted from the second emission unit 152. For example, mixed light of the light emitted from the first emission unit 151 and the light emitted from the second emission unit 152 may be white light, but embodiments of the present disclosure are not limited thereto.
[0767] The hole transport region 120 is located between the first emission unit 151 and the first electrode 110 , and the second emission unit 152 may include the first hole transport region 121 located on one side of the first electrode 110 .
[0768] The electron transport region 170 is located between the second emission unit 152 and the second electrode 190, and the first emission unit 151 may include a first electron transport region 171 located between the charge generation layer 141 and the first emission layer 151-EM.
[0769] The first emission layer 151 -EM may include a host, a cooling dopant, and a sensitizer, and the cooling dopant and the sensitizer may satisfy conditions 1 and 2.
[0770] The second emission layer 152 -EM may include a host, a cooling dopant, and a sensitizer, and the cooling dopant and the sensitizer may satisfy conditions 1 and 2.
[0771] Figure 3 The first electrode 110 and the second electrode 190 shown in FIG. Figure 1 The first electrode 11 and the second electrode 19 shown in FIG. 1 are the same as described above.
[0772] Figure 3 The first emission layer 151-EM and the second emission layer 152-EM shown in FIG. Figure 1 The emission layer 15 shown in FIG. 1 is the same as described above.
[0773] Figure 3 The hole transport region 120 and the first hole transport region 121 shown in FIG. Figure 1 The hole transport region 12 shown in FIG. 1 is the same as described above.
[0774] Figure 3 The electron transport region 170 and the first electron transport region 171 shown in FIG. Figure 1 The electron transport region 17 shown in FIG. 1 is the same as described above.
[0775] As mentioned above, reference Figure 3 , an organic light emitting device in which the first emission unit 151 and the second emission unit 152 each include an emission layer including a host, a cooling dopant, and a sensitizer has been described. However, the organic light emitting device may have various other forms. For example, Figure 3 One of the first emission unit 151 and the second emission unit 152 of the organic light emitting device 100 may be replaced with any known emission unit, or may include three or more emission units.
[0776] [ Figure 4 Description]
[0777] Figure 4 is a schematic cross-sectional view of an organic light emitting device 200 according to another embodiment.
[0778] The organic light emitting device 200 includes a first electrode 210 , a second electrode 290 facing the first electrode 210 , and first and second emission layers 251 and 252 stacked between the first and second electrodes 210 and 290 .
[0779] The maximum emission wavelength of light emitted from the first emission layer 251 may be different from the maximum emission wavelength of light emitted from the second emission layer 252. For example, mixed light of light emitted from the first emission layer 251 and light emitted from the second emission layer 252 may be white light, but embodiments of the present disclosure are not limited thereto.
[0780] In one or more embodiments, the hole transport region 220 may be located between the first emission layer 251 and the first electrode 210 , and the electron transport region 270 may be located between the second emission layer 252 and the second electrode 290 .
[0781] The first emission layer 251 may include a host, a cooling dopant, and a sensitizer, and the cooling dopant and the sensitizer may satisfy conditions 1 and 2.
[0782] The second emission layer 252 may include a host, a cooling dopant, and a sensitizer, and the cooling dopant and the sensitizer may satisfy conditions 1 and 2.
[0783] Figure 4 The first electrode 210, the hole transport region 220 and the second electrode 290 shown in FIG. Figure 1 The first electrode 11, the hole transport region 12 and the second electrode 19 shown in FIG. 1 are the same as described above.
[0784] Figure 4 The first emission layer 251 and the second emission layer 252 shown in FIG. Figure 1 The emission layer 15 shown in FIG. 1 is the same as described above.
[0785] Figure 4 The electron transport region 270 shown in FIG. Figure 1 The electron transport region 17 is the same as described above.
[0786] As mentioned above, reference Figure 4 , an organic light emitting device in which the first emission layer 251 and the second emission layer 252 each include a host, a cooling dopant, and a sensitizer has been described. However, the organic light emitting device may have various other forms. For example, Figure 4One of the first emission layer 251 and the second emission layer 252 of the organic light emitting device 200 may be replaced with any known emission layer, or an intermediate layer may be additionally provided between adjacent emission layers.
[0787] Explanation of terminology
[0788] As used herein, the term "C 1 -C 60 "Alkyl" refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl. As used herein, the term "C 1 -C 60 "Alkylene" refers to a group having a C 1 -C 60 Alkyl is a divalent group of the same structure.
[0789] The term "C 1 -C 60 "Alkoxy" refers to a 101 (A 101 C 1 -C 60 An alkyl group is a monovalent group represented by an alkyl group, and examples thereof include a methoxy group, an ethoxy group and an isopropoxy group.
[0790] As used herein, the term "C 2 -C 60 "Alkenyl" refers to a group consisting of 2 -C 60 The term "C" as used herein refers to a hydrocarbon group formed by inserting at least one carbon-carbon double bond in the middle or at the terminal of an alkyl group, and examples thereof include ethenyl, propenyl, and butenyl. 2 -C 60 "Alkenylene" refers to a 2 -C 60 Alkenyl is a divalent group of the same structure.
[0791] As used herein, the term "C 2 -C 60 "Alkynyl" refers to a 2 -C 60 The term "C" as used herein refers to a hydrocarbon group formed by inserting at least one carbon-carbon triple bond in the middle or at the terminal of an alkyl group, and examples thereof include ethynyl and propynyl. 2 -C 60 "Alkyne" refers to a group having a C 2 -C 60 Alkynyl is a divalent group of the same structure.
[0792] As used herein, the term "C 3 -C 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. As used herein, the term "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. 3 -C 10 "Cycloalkylene" refers to a cycloalkylene having a 3 -C 10 Cycloalkyl is a divalent group of the same structure.
[0793] As used herein, the term "C 1 -C 10 "Heterocycloalkyl" refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, P, Si and S as a ring atom and 1 to 10 carbon atoms, and non-limiting examples thereof include tetrahydrofuranyl and tetrahydrothienyl. As used herein, the term "C 1 -C 10 "Heterocycloalkylene" refers to a group having a C 1 -C 10 Heterocycloalkyl is a divalent group of the same structure.
[0794] As used herein, the term "C 3 -C 10 "Cycloalkenyl" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and not having aromaticity, and non-limiting examples thereof include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C 3 -C 10 "Cycloalkenylene" refers to a 3 -C 10 Cycloalkenyl is a divalent group of the same structure.
[0795] As used herein, the term "C 1 -C 10 The term "heterocycloalkenyl" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, P, Si and S as a ring atom, 1 to 10 carbon atoms, and at least one carbon-carbon double bond in its ring. 1 -C 10 Examples of heterocycloalkenyl are 2,3-dihydrofuranyl and 2,3-dihydrothienyl. 1 -C 10 "Heterocycloalkenylene" refers to a 1 -C 10 Heterocycloalkenyl is a divalent group of the same structure.
[0796] As used herein, the term "C 6 -C60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the term "C 6 -C 60 "Arylene" refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. 6 -C 60 Examples of aryl groups include phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, and When C 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each include two or more rings, the rings may be fused to each other.
[0797] As used herein, the term "C 1 -C 60 "Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system having at least one heteroatom selected from N, O, P, Si and S as a ring atom, and 1 to 60 carbon atoms. As used herein, the term "C 1 -C 60 The term "heteroarylene" refers to a divalent group having a heterocyclic aromatic system having at least one heteroatom selected from N, O, P, Si and S as a ring atom, and 1 to 60 carbon atoms. 1 -C 60 Examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, and isoquinolyl. 6 -C 60 Heteroaryl and C 6 -C 60 When the heteroarylene groups each include two or more rings, the rings may be fused to each other.
[0798] As used herein, the term "C 6 -C 60 "Aryloxy" refers to -OA 102 (A 102 C 6 -C 60 aryl), and C 6 -C 60 Arylthio refers to -SA 103 (A 103 C 6 -C 60 aryl).
[0799] The term "monovalent non-aromatic fused polycyclic group" as used herein refers to a monovalent group in which two or more rings are fused to each other, only carbon is used as a ring-forming atom (e.g., the number of carbon atoms may be 8-60), and the entire molecule is a non-aromatic group. Examples of monovalent non-aromatic fused polycyclic groups include fluorenyl. As used herein, the term "divalent non-aromatic fused polycyclic group" refers to a divalent group having the same structure as a monovalent non-aromatic fused polycyclic group.
[0800] The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group having two or more rings fused to each other, having a heteroatom selected from N, O, P, Si and S as a ring-forming atom in addition to carbon atoms (e.g., having 1 to 60 carbon atoms), and having no aromaticity in its entire molecular structure. The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic fused heteropolycyclic group.
[0801] As used herein, the term "C 5 -C 30 The term "carbocyclic group" refers to a saturated or unsaturated cyclic group having only 5 to 30 carbon atoms as ring atoms. 5 -C 30 The carbocyclic group may be a monocyclic group or a polycyclic group and, depending on the formula structure, may be a monovalent, divalent, trivalent, tetravalent, pentavalent, or hexavalent group.
[0802] As used herein, the term "C 1 -C 30 The term "heterocyclic group" refers to a saturated or unsaturated cyclic group having at least one heteroatom selected from N, O, Si, P and S as a ring atom in addition to 1 to 30 carbon atoms. 1 -C 30 The heterocyclic group may be a monocyclic group or a polycyclic group, and may be a monovalent, divalent, trivalent, tetravalent, pentavalent, or hexavalent group depending on the formula structure.
[0803] Substituted C 5 -C 60 Carbocyclic groups, substituted C 1 -C 60 Heterocyclic groups, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 At least one substituent of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group may be selected from:
[0804] Deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, and C 1 -C 60 Alkoxy;
[0805] Each of the following C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, and C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 3 -C 10 Cycloalkyl, C 1-C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 ), and -P(=O)(Q 18 )(Q 19 );
[0806] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups;
[0807] Each of the following C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, and monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 22 )、-Si(Q 23 )(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 ), and -P(=O)(Q 28 )(Q 29 );and
[0808] -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 ), and -P(=O)(Q 38 )(Q 39 ),
[0809] Where Q 1 -Q 9 , Q 11 -Q 19 , Q 21 -Q 29 and Q 31 -Q 39 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, selected from C 1 -C 60 Alkyl and C 6 -C 60 At least one substituted C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heteropolycyclic group.
[0810] As used herein, the term "room temperature" refers to a temperature of about 25°C.
[0811] The terms "biphenyl, terphenyl, and quaterphenyl" as used herein refer to monovalent groups in which two, three, or four phenyl groups are linked via a monovalent bond, respectively.
[0812] The term "phenyl containing cyano group, biphenyl containing cyano group, terphenyl containing cyano group, and quaterphenyl containing cyano group" used herein refers to phenyl, biphenyl, terphenyl, and quaterphenyl each substituted by at least one cyano group. In "phenyl containing cyano group, biphenyl containing cyano group, terphenyl containing cyano group, and quaterphenyl containing cyano group", cyano group can be substituted to any position of the corresponding group, and "phenyl containing cyano group, biphenyl containing cyano group, terphenyl containing cyano group, and quaterphenyl containing cyano group" can further include substituents different from cyano group. For example, phenyl substituted by cyano group, and phenyl substituted by cyano group and methyl group can all belong to "phenyl containing cyano group".
[0813] Hereinafter, the compound and the organic light-emitting device according to the embodiment are described in detail with reference to the synthesis examples and the examples. However, the organic light-emitting device is not limited thereto. The phrase "using 'B' instead of 'A'" used in describing the synthesis examples means that in terms of molar equivalents, the amount of 'A' used is the same as the amount of 'B' used.
[0814] [Example]
[0815] Evaluation Example 1: Decay Time Measurement
[0816] On a quartz substrate, the compounds of Tables 5 to 7 were mixed at a weight ratio of 10 -7 The vacuum co-deposition was carried out at a vacuum degree of 1000 to manufacture a film each having a thickness of 40nm. For each of the films, the PL spectrum was evaluated at room temperature by using PicoQuant Inc.'s FluoTime 300 and PicoQuant Inc.'s PLS340 (excitation wavelength = 340nm, and spectrum width = 20nm) as a pump light source. In detail, the wavelength of the main peak of the spectrum obtained for each film is determined, and the number of photons emitted from the corresponding sample at the wavelength of the main peak by the photon pulse (pulse width = 500ps) applied to the corresponding film by PLS340 is repeatedly measured based on time-correlated single photon counting (TCSPC) to obtain a TRPL curve, which can be fitted. Two or more exponential decay functions obtained therefrom are subjected to fitting to calculate the decay time for each film. At this point, the same measurement is carried out under dark conditions (blocking the light low pulse signal incident on the predetermined film) for the same measurement time as used to obtain the TRPL curve to obtain a background signal curve, and then the background signal curve is fitted. The result is used as a baseline.
[0817] At this time, in the case of the film of Table 5, the function used for fitting is the same as the following equation A, and the maximum value among Tau (τ) obtained therefrom is taken. For the films of Tables 6 and 7 below, the Tau value (Tau) obtained by fitting is used. 1 , Tau 2 , Tau 3 etc.) and amplitude value (A 1 , A 2 , A 3 Etc.) Tau is obtained by Equation B:
[0818] <Equation A>
[0819]
[0820] <Equation B>
[0821]
[0822] [Table 5]
[0823] Film No. Membrane composition (weight ratio) Decay time(μs) SP002ND H-H1:H-E1:SP002(45:45:10) 2.393 SP003ND H-H1:H-E1:SP003(45:45:10) 2.703 SP004ND H-H1:H-E1:SP004(45:45:10) 4.924 SP005ND H-H1:H-E1:SP005(45:45:10) 2.866 SP006ND H-H1:H-E1:SP006(45:45:10) 1.836 SP007ND H-H1:H-E1:SP007(45:45:10) 2.223 ST001ND H-H1:H-E1:ST001(45:45:10) 1.13 ST002ND H-H1:H-E1:ST002(45:45:10) 2.69
[0824] Table 6
[0825]
[0826]
[0827] Table 7
[0828] Film No. Membrane composition (weight ratio) Decay time(μs) FD001 H-H1:H-E1:FD11(47.5:47.5:5) 0.027 FD002 H-H1:H-E1:FD5(47.5:47.5:5) 0.069
[0829]
[0830] Example 1
[0831] The ITO glass substrate was cut into a size of 50 mm×50 mm×0.5 mm, and then sonicated in acetone, isopropyl alcohol, and pure water for 15 minutes each, and then washed by exposure to UV ozone for 30 minutes.
[0832] Then, F6-TCNNQ was deposited on the ITO electrode (anode) of the glass substrate to form a A hole injection layer having a thickness of , and HT1 is deposited on the hole injection layer to form a A hole transport layer with a thickness of , thereby completing the hole transport region.
[0833] Compound H-H1 (first host), H-E1 (second host), compound SP002 (sensitizer) (in this case, the weight ratio of the first host, the second host and the sensitizer is 45:45:10) and FD11 (cooling dopant) (in this case, the cooling dopant is 5 wt % based on the total weight of the first host, the second host, the sensitizer and the cooling dopant) are co-deposited on the hole transport region to form a The thickness of the emission layer.
[0834] Compound ET17 and Liq were co-deposited on the emission layer at a weight ratio of 5:5 to form a Then, LiQ is deposited on the electron transport layer to form an electron transport layer having a thickness of An electron injection layer with a thickness of , and Al is deposited on the electron injection layer to The organic light-emitting device is thus completed.
[0835] Examples 2 to 12
[0836] An organic light emitting device was manufactured in the same manner as in Example 1, except that when forming the emission layer, the sensitizer and cooling dopant shown in Table 8 were used.
[0837] Table 8
[0838]
[0839]
[0840] Comparative Examples 1F and 2F
[0841] An organic light emitting device was manufactured in the same manner as in Example 1, except that when forming the emission layer, no sensitizer was used and the first host, the second host, and the cooling dopant were used as shown in Table 9.
[0842] Table 9
[0843]
[0844] Comparative Examples 1P to 6P
[0845] An organic light emitting device was manufactured in the same manner as in Example 1, except that when forming the emission layer, no cooling dopant was used and the first host, the second host, and the sensitizer were used as shown in Table 10.
[0846] Table 10
[0847]
[0848] Comparative Examples 1T and 2T
[0849] An organic light emitting device was manufactured in the same manner as in Example 1, except that when forming the emission layer, no cooling dopant was used and the first host, the second host, and the sensitizer were used as shown in Table 11.
[0850] Table 11
[0851]
[0852] Evaluation Example 2: OLED Lifetime and External Quantum Efficiency Measurement
[0853] The external quantum efficiency (EQE) and life of each of the organic light-emitting devices manufactured according to Examples 1 to 12 were evaluated, and then the results were calculated as relative values (%), and the results are shown in Table 12. As an evaluation device, a luminance meter (Minolta Cs-1000A) was used. The life (T) was determined by evaluating the time taken for the initial luminance of 100% to become 95% under the same luminance measurement conditions. 95 ).
[0854] In addition, after measuring the lifetime and EQE of Example 3, Comparative Examples 3P, 1F and 2F, the relative value (%) was calculated based on the value of Comparative Example 1F, and the results are shown in Table 13 and Figure 5 and 6 middle.
[0855] Table 12
[0856]
[0857] Referring to Table 12, it can be seen that the organic light emitting devices of Examples 1 to 12 have a long lifespan and high efficiency.
[0858] Table 13
[0859]
[0860] Refer to Table 13 and Figure 5 and 6 It can be seen that, compared with the phosphorescent organic light-emitting device (Comparative Example 3P) and the fluorescent organic light-emitting device (Comparative Example 1F), the organic light-emitting device of Example 3 has a long lifetime and a high EQE.
[0861] Evaluation Example 3: Calculation of OLED Lifetime Increment
[0862] For Examples 1 to 12 and Comparative Examples 1F and 2F, the time taken for the initial luminance of 100% to decrease to 95% thereof at 6000 nits (T 95). Then, the life increments of Examples 1 to 12 were calculated using the following equation L and the results are shown in Table 14.
[0863] <Equation L>
[0864] The life increment of device A = {T 95} / {T of device B 95}
[0865] Table 14
[0866] Device A Device B Lifetime increment of device A Example 1 Comparative Example 1F 5.8 Example 2 Comparative Example 1F 4.6 Example 3 Comparative Example 1F 22.3 Example 4 Comparative Example 1F 9.74 Example 5 Comparative Example 1F 5.70 Example 6 Comparative Example 2F 1.84 Example 7 Comparative Example 1F 4.17 Example 8 Comparative Example 2F 1.5 Example 9 Comparative Example 1F 11.3 Example 10 Comparative Example 2F 6.14 Embodiment 11 Comparative Example 1F 5.74 Example 12 Comparative Example 2F 3.46
[0867] Referring to Table 14, it can be seen that the organic light emitting devices of Examples 1 to 12 have significant improvements in lifespan compared to the fluorescent organic light emitting devices of Comparative Examples 1F and 2F that do not include a sensitizer.
[0868] Evaluation Example 4: Calculation of OLED EQE increment
[0869] For Examples 1 to 12, Comparative Examples 1P to 6P, and Comparative Examples 1T and 2T, the external quantum efficiency (EQE) was measured. Then, the EQE increments of Examples 1 to 12 were calculated using the following Equation E.
[0870] <Equation E>
[0871] EQE increment of device C = {EQE of device C} / {EQE of device D}
[0872] Table 15
[0873] Device C Device D EQE increment of device C Example 1 Comparative Example 1P 5.78 Example 2 Comparative Example 2P 4.52 Example 3 Comparative Example 3P 3.85 Example 4 Comparative Example 4P 3.19 Example 5 Comparative Example 5P 4.26 Example 6 Comparative Example 5P 1.66 Example 7 Comparative Example 6P 4.60 Example 8 Comparative Example 6P 2.02 Example 9 Comparative Example 1T 2.07 Example 10 Comparative Example 1T 1.40 Embodiment 11 Comparative Example 2T 4.11 Example 12 Comparative Example 2T 2.62
[0874] Referring to Table 15, it can be seen that the organic light-emitting devices of Examples 1 to 12 show significant improvement in EQE compared to Comparative Examples 1P to 6P, phosphorescent 1T and 2T, or TADF organic light-emitting devices that do not include a cooling dopant.
[0875] The organic light emitting device may have a long lifetime.
[0876] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for limiting purposes. The description of features or aspects in each embodiment should typically be considered to be applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, it will be understood by those of ordinary skill in the art that various changes in form and detail may be made therein without departing from the spirit and scope as defined by the appended claims.
Claims
1. Organic light-emitting device, comprising: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode; The organic layer includes an emission layer; The emission layer includes a host, a cooling dopant and a sensitizer, The subject comprises one of (a) to (d): (a) an electronic transmission subject, (b) an amphoteric host, an electron transport host, and a hole transport host, (c) an electron transport host and a hole transport host, or (d) amphiphilic hosts and hole transport hosts, wherein the electron transport host comprises at least one electron transport moiety, The hole transport host does not include an electron transport moiety, The electron transport moiety is a cyano group, a cyclic group containing π-electron-deficient nitrogen, a group represented by one of the following formulae, or a combination thereof: Wherein *, *' and *" in the above formula are each a binding site with an adjacent atom; wherein the cooling dopant and the sensitizer satisfy conditions 1 and 2, and The sensitizer includes platinum (Pt): <Condition 1> T 衰减 (CD) <T 衰减 (S) <Condition 2> T 衰减 (CD)<1.5μs Among them, in conditions 1 and 2, T 衰减 (CD) is the decay time of the cooling dopant, and T 衰减 (S) is the decay time of the sensitizer.
2. Organic light-emitting device, comprising: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode; The organic layer includes an emission layer; The emission layer includes a host, a cooling dopant and a sensitizer, wherein The cooling dopant and the sensitizer satisfy conditions 1, 2 and 3, and The sensitizer includes a thermally activated delayed fluorescent emitter, and Thermally activated delayed fluorescence emitters do not include metals: <Condition 1> T 衰减 (CD) <T 衰减 (S) <Condition 2> T 衰减 (CD)<1.5μs <Condition 3> T 衰减 (CD) / T 衰减 (S)<0.5 Among them, in conditions 1, 2 and 3, T 衰减 (CD) is the decay time of the cooling dopant, and T 衰减 (S) is the decay time of the sensitizer.
3. Organic light-emitting device, comprising: a first electrode; a second electrode; m emission units, which are located between the first electrode and the second electrode and include at least one emission layer; as well as m-1 charge generation layers, which are between two adjacent emission units of the m emission units and include an n-type charge generation layer and a p-type charge generation layer, m is an integer of 2 or greater, The maximum emission wavelength of light emitted from at least one of the m emission units is different from the maximum emission wavelength of light emitted from at least one of the remaining emission units, The emission layer includes a host, a cooling dopant and a sensitizer, The subject comprises one of (a) to (d): (a) an electronic transmission subject, (b) an amphoteric host, an electron transport host, and a hole transport host, (c) an electron transport host and a hole transport host, or (d) amphiphilic hosts and hole transport hosts, wherein the electron transport host comprises at least one electron transport moiety, The hole transport host does not include an electron transport moiety, The electron transport moiety is a cyano group, a cyclic group containing π-electron-deficient nitrogen, a group represented by one of the following formulae, or a combination thereof: Wherein *, *' and *" in the above formula are each a binding site with an adjacent atom; wherein the cooling dopant and the sensitizer satisfy conditions 1 and 2, and The sensitizer includes platinum (Pt): <Condition 1> T 衰减 (CD) <T 衰减 (S) <Condition 2> T 衰减 (CD)<1.5μs Among them, in conditions 1 and 2, T 衰减 (CD) is the decay time of the cooling dopant, and T 衰减 (S) is the decay time of the sensitizer.
4. Organic light-emitting device, comprising: a first electrode; a second electrode; m emission units, which are located between the first electrode and the second electrode and include at least one emission layer; as well as m-1 charge generation layers, which are between two adjacent emission units of the m emission units and include an n-type charge generation layer and a p-type charge generation layer, m is an integer of 2 or greater, The maximum emission wavelength of light emitted from at least one of the m emission units is different from the maximum emission wavelength of light emitted from at least one of the remaining emission units, The emission layer includes a host, a cooling dopant and a sensitizer, wherein The cooling dopant and the sensitizer satisfy conditions 1, 2 and 3, and The sensitizer includes a thermally activated delayed fluorescent emitter, and Thermally activated delayed fluorescence emitters do not include metals: <Condition 1> T 衰减 (CD) <T 衰减 (S) <Condition 2> T 衰减 (CD)<1.5μs <Condition 3> T 衰减 (CD) / T 衰减 (S)<0.5 Among them, in conditions 1, 2 and 3, T 衰减 (CD) is the decay time of the cooling dopant, and T 衰减 (S) is the decay time of the sensitizer.
5. Organic light-emitting device, comprising: a first electrode; a second electrode; and m emission layers between the first electrode and the second electrode, m is an integer of 2 or greater, a maximum emission wavelength of light emitted from at least one emission layer of the m emission layers is different from a maximum emission wavelength of light emitted from at least one emission layer of the remaining emission layers, The emission layer includes a host, a cooling dopant and a sensitizer, The subject comprises one of (a) to (d): (a) an electronic transmission subject, (b) an amphoteric host, an electron transport host, and a hole transport host, (c) an electron transport host and a hole transport host, or (d) amphiphilic hosts and hole transport hosts, wherein the electron transport host comprises at least one electron transport moiety, The hole transport host does not include an electron transport moiety, The electron transport moiety is a cyano group, a cyclic group containing π-electron-deficient nitrogen, a group represented by one of the following formulae, or a combination thereof: Wherein *, *' and *" in the above formula are each a binding site with an adjacent atom; wherein the cooling dopant and the sensitizer satisfy conditions 1 and 2, and The sensitizer includes platinum (Pt): <Condition 1> T 衰减 (CD) <T 衰减 (S) <Condition 2> T 衰减 (CD)<1.5μs Among them, in conditions 1 and 2, T 衰减 (CD) is the decay time of the cooling dopant, and T 衰减 (S) is the decay time of the sensitizer.
6. Organic light-emitting device, comprising: a first electrode; a second electrode; and m emission layers between the first electrode and the second electrode, m is an integer of 2 or greater, a maximum emission wavelength of light emitted from at least one emission layer of the m emission layers is different from a maximum emission wavelength of light emitted from at least one emission layer of the remaining emission layers, The emission layer includes a host, a cooling dopant and a sensitizer, wherein The cooling dopant and the sensitizer satisfy conditions 1, 2 and 3, and The sensitizer includes a thermally activated delayed fluorescent emitter, and Thermally activated delayed fluorescence emitters do not include metals: <Condition 1> T 衰减 (CD) <T 衰减 (S) <Condition 2> T 衰减 (CD)<1.5μs <Condition 3> T 衰减 (CD) / T 衰减 (S)<0.5 Among them, in conditions 1, 2 and 3, T 衰减 (CD) is the decay time of the cooling dopant, and T 衰减 (S) is the decay time of the sensitizer.
7. The organic light emitting device according to claim 1, 3 or 5, wherein The organic light-emitting device further satisfies condition 3: <Condition 3> T 衰减 (CD) / T 衰减 (S)<0.5 in, In condition 3, T 衰减 (CD) is the decay time of the cooling dopant, and T 衰减 (S) is the decay time of the sensitizer.
8. The organic light emitting device according to any one of claims 1 to 6, wherein The organic light-emitting device further satisfies condition 4: <Condition 4> BDE(S)-T1(S)<3.0eV in, In condition 4, BDE(S) is the bond dissociation energy level of the sensitizer, and T1(S) is the lowest excited triplet energy level of the sensitizer.
9. The organic light emitting device according to any one of claims 1 to 6, wherein The organic light-emitting device further satisfies condition 5: <Condition 5> R(Hex) / e 10 <15 in, In condition 5, R(Hex) is the rate of generation of thermal excitons.
10. The organic light emitting device according to any one of claims 1 to 6, wherein The host, dopant and sensitizer further satisfy condition 6: <Condition 6> T1(H)≥T1(S)≥S1(CD) in, In condition 6, T1(H) is the lowest excited triplet energy level of the host, T1(S) is the lowest excited triplet energy level of the sensitizer, and S1(CD) is the lowest excited singlet energy level of the cooling dopant.
11. The organic light emitting device according to any one of claims 1 to 6, wherein The emission layer is composed of the host, cooling dopants and sensitizers.
12. The organic light emitting device according to any one of claims 2, 4 or 6, wherein The host includes an amphoteric host, an electron transport host, and / or a hole transport host, The electron transport host includes at least one electron transport moiety, The hole transport host does not include an electron transport moiety, The electron transport moiety is selected from a cyano group, a cyclic group containing π-electron-deficient nitrogen, and a group represented by one of the following formulae: Wherein *, *' and *" in the above formula are each a binding site with an adjacent atom.
13. The organic light emitting device according to any one of claims 1, 3 or 5, wherein The electron transport host comprises at least one cyclic group not containing π-electron-deficient nitrogen and at least one electron transport moiety, The hole transport host includes at least one cyclic group that does not contain π-electron-deficient nitrogen and does not include an electron transport moiety, and The electron transporting moiety is a cyano group or a cyclic group containing π-electron-deficient nitrogen.
14. The organic light emitting device according to claim 12, wherein The electron transport host comprises at least one cyclic group not containing π-electron-deficient nitrogen and at least one electron transport moiety, The hole transport host includes at least one cyclic group that does not contain π-electron-deficient nitrogen and does not include an electron transport moiety, and The electron transporting moiety is a cyano group or a cyclic group containing π-electron-deficient nitrogen.
15. The organic light emitting device according to claim 13, wherein The cyclic group containing π-electron-deficient nitrogen is selected from: imidazole group, pyrazole group, thiazole group, isothiazole group, Azole group, iso azole group, pyridine group, pyrazine group, pyridazine group, pyrimidine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cinnoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzimidazole group, isobenzothiazole group, benzo Azole group, isobenzo Azole group, triazole group, tetrazole group, a oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group; and a fused ring group of two or more cyclic groups containing π-electron-deficient nitrogen, The cyclic group not containing π-electron-deficient nitrogen is selected from a phenyl group, a heptadene group, an indene group, a naphthalene group, group, indacene group, acenaphthene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenanthene group, phenanthren group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, Group, tetraphenyl group, group, a perylene group, a pentacene group, a hexacenyl group, a pentaphene group, a rubine group, a coronene group, an ovalenyl group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofuranocarbazole group, a benzothiophenocarbazole group, and a triindolophenyl group; and a fused ring group of two or more cyclic groups that do not contain π-electron-deficient nitrogen.
16. The organic light emitting device according to claim 14, wherein The cyclic group containing π-electron-deficient nitrogen is selected from: imidazole group, pyrazole group, thiazole group, isothiazole group, Azole group, iso azole group, pyridine group, pyrazine group, pyridazine group, pyrimidine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cinnoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzimidazole group, isobenzothiazole group, benzo Azole group, isobenzo Azole group, triazole group, tetrazole group, a oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group; and a fused ring group of two or more cyclic groups containing π-electron-deficient nitrogen, The cyclic group not containing π-electron-deficient nitrogen is selected from a phenyl group, a heptadene group, an indene group, a naphthalene group, group, indacene group, acenaphthene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenanthene group, phenanthren group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, Group, tetraphenyl group, group, a perylene group, a pentacene group, a hexacenyl group, a pentaphene group, a rubine group, a coronene group, an ovalenyl group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofuranocarbazole group, a benzothiophenocarbazole group, and a triindolophenyl group; and a fused ring group of two or more cyclic groups that do not contain π-electron-deficient nitrogen.
17. The organic light emitting device according to any one of claims 1, 3 or 5, wherein The electron transport host includes i) at least one of a cyano group, a pyrimidine group, a pyrazine group, and a triazine group and ii) a benzo[9,10]phenanthrene group, and The hole transport host includes a carbazole group.
18. The organic light emitting device according to claim 12, wherein The electron transport host includes i) at least one of a cyano group, a pyrimidine group, a pyrazine group, and a triazine group and ii) a benzo[9,10]phenanthrene group, and The hole transport host includes a carbazole group.
19. The organic light emitting device according to any one of claims 1 to 6, wherein the maximum emission wavelength of the emission spectrum of the cooling dopant is 400 nm or more and 550 nm or less.
20. An organic light emitting device as claimed in any one of claims 1 to 6, wherein the cooling dopant does not comprise a metal atom.
21. The organic light emitting device according to any one of claims 1 to 6, wherein The cooling dopant includes a core containing naphthalene, a core containing fluorene, a core containing spiro-bifluorene, a core containing benzofluorene, a core containing dibenzofluorene, a core containing phenanthrene, a core containing anthracene, a core containing fluoranthene, a core containing benzo[9,10]phenanthrene, a core containing pyrene, a core containing The core of tetracene, the core of A core containing perylene, a core containing pentaphene, a core containing indenoanthracene, a core containing bianthracene, and one of the cores represented by 501-1 to 501-18:
22. An organic light emitting device as claimed in claim 1, 3 or 5, wherein The sensitizer includes an organometallic compound represented by Formula 101: <Formula 101> Pt(L 11 ) n11 (L 12 ) n12 in, In formula 101, L 11 is a ligand represented by one of formulae 1-1 to 1-4; L 12 is selected from a monodentate ligand and a bidentate ligand; n11 is 1, n12 is selected from 0, 1 and 2; Among them, in formulas 1-1 to 1-4, A1-A4 are each independently selected from substituted or unsubstituted C5-C 30 Carbocyclic group, substituted or unsubstituted C1-C 30 Heterocyclic groups, and non-cyclic groups, Y 11 -Y 14 Each independently represents a chemical bond, O, S, N (R 91 )、B(R 91 )、P(R 91 ), or C(R 91 )(R 92 ), T1-T4 are each independently selected from a single bond, a double bond, *-N(R 93 )-*'、*-B(R 93 )-*'、*-P(R 93 )-*'、*-C(R 93 )(R 94 )-*'、*-Si(R 93 )(R 94 )-*'、*-Ge(R 93 )(R 94 )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R 93 )=*'、*=C(R 93 )-*'、*-C(R 93 )=C(R 94 )-*', *-C(=S)-*', and *-C≡C-*', Substituted C5-C 30 Substituents of carbocyclic groups, substituted C1-C 30 The substituent of the heterocyclic group, and R 91 -R 94 Each is independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphate or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), and -P(=S)(Q1)(Q2), wherein the substituted C5-C 30 Substituents of carbocyclic groups and substituted C1-C 30 The substituents of the heterocyclic group are each not hydrogen, *1, *2, *3, and *4 each represent a binding site with Pt, and Q1-Q3 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C7-C 60 Alkaryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, selected from deuterium, -F, cyano, C1-C 60 Alkyl, and C6-C 60 At least one substituted C1-C 60 Alkyl, and is selected from deuterium, -F, cyano, C1-C 60 Alkyl, and C6-C 60 At least one substituted C6-C 60 Aryl.
23. An organic light emitting device as claimed in claim 2, 4 or 6, wherein The sensitizer satisfies condition 7: <Condition 7> ΔE ST ≤0.3eV in, In condition 7, ΔE ST is the difference between the lowest excited singlet energy level and the lowest excited triplet energy level of the sensitizer.
24. An organic light emitting device as claimed in claim 2, 4 or 6, wherein The sensitizer is represented by formula 201 or 202: in, In equations 201 and 202, A 21 is the acceptor group, D 21 is the donor group, m21 is 1, 2 or 3, and n21 is 1, 2 or 3, The sum of n21 and m21 in formula 201 is 6 or less, and the sum of n21 and m21 in formula 202 is 5 or less, R 21 is selected from hydrogen, deuterium, -F, -Cl, -Br, -I, SF5, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C7-C 60 Alkaryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryloxy, substituted or unsubstituted C1-C 60 heteroarylthio, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), and -P(=S)(Q1)(Q2), multiple R 21 are optionally linked together to form a substituted or unsubstituted C5-C 30 Carbocyclic group or substituted or unsubstituted C1-C 30 Heterocyclic groups, Q1-Q3 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C7-C 60 Alkaryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, selected from deuterium, -F, cyano, C1-C 60 Alkyl, and C6-C 60 At least one substituted C1-C 60 Alkyl, and is selected from deuterium, -F, cyano, C1-C 60 Alkyl, and C6-C 60 At least one substituted C6-C 60 Aryl.
25. The organic light emitting device according to claim 24, wherein A 21 is a substituted or unsubstituted cyclic group that does not contain π-electron-deficient nitrogen; D 21 Selected from: -F, cyano, and cyclic groups containing π-electron-deficient nitrogen; C1-C ... 60 an alkyl group, a cyclic group containing a π-electron-deficient nitrogen, and a cyclic group not containing a π-electron-deficient nitrogen; and Each is selected from deuterium, C1-C 60 an alkyl group, a cyclic group containing π-electron-deficient nitrogen, and a cyclic group not containing π-electron-deficient nitrogen that is substituted with at least one of an alkyl group, a cyclic group containing π-electron-deficient nitrogen, and a cyclic group containing no π-electron-deficient nitrogen; The cyclic group not containing π-electron-deficient nitrogen is selected from a phenyl group, a heptadene group, an indene group, a naphthalene group, group, indacene group, acenaphthene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenanthene group, phenanthren group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, Group, tetraphenyl group, a phenylene group, a perylene group, a pentacene group, a hexaphenylene group, a pentylene group, a rubine group, a coronene group, an ovalene group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofuranocarbazole group, a benzothiophenocarbazole group, and a triindolophenyl group; and a fused ring group of two or more cyclic groups that do not contain π-electron-deficient nitrogen, and The cyclic group containing π-electron-deficient nitrogen is a cyclic group having at least one *-N=*' portion and is selected from an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, Azole group, iso azole group, pyridine group, pyrazine group, pyridazine group, pyrimidine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cinnoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzimidazole group, isobenzothiazole group, benzo Azole group, isobenzo Azole group, triazole group, tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, an azacarbazole group, and a benzimidazolobenzimidazole group; and a condensed ring group of two or more π-electron-deficient nitrogen-containing cyclic groups.
Citation Information
Patent Citations
Semi-crystalline thermoplastic polyester for producing biaxially oriented films
KR1020190037245A
Hydraulic fluid and fuel resistant sealants
KR1020200027986A
Highly efficient oled devices with very short decay times
CN107735880A
Composition, thin film, and organic light emitting device including composition and thin film
EP3142162A1