Condensed heterocyclic compound, light-emitting device, and electronic apparatus

Abstract

Disclosed are a condensed heterocyclic compound, a light-emitting device, and an electronic apparatus. The light emitting device includes a first electrode, a second electrode, and an emission layer between the first electrode and the second electrode, where the emission layer includes a condensed heterocyclic compound represented by Chemical Formula 1, where variables in Chemical Formula 1 are the same as defined in the specification. In addition, an electronic apparatus including the light emitting device, an electronic apparatus including the light emitting device, and a condensed heterocyclic compound are also provided. Chemical formula 1

Description

Condensed heterocyclic compounds, light-emitting devices and electronic devices

[0001] This application claims priority and benefit to Korean Patent Application No. 10-2024-0151850, filed on October 31, 2024, with the Korean Intellectual Property Office, and Korean Patent Application No. 10-2025-0114446, filed on August 18, 2025, with the entire disclosure of which is incorporated herein by reference. Technical Field

[0002] One or more embodiments of this application relate to a condensed heterocyclic compound, a light-emitting device, and an electronic device. Background Technology

[0003] Organic light-emitting devices (OLEDs) exhibit self-emissive properties under driving voltage and can provide improved viewing angle and contrast properties. Furthermore, compared to other light-emitting devices of comparable technologies, OLEDs offer high response speed and high brightness.

[0004] Organic light-emitting devices may include an emission layer disposed between a first electrode and a second electrode. Holes provided from the first electrode and electrons provided from the second electrode can recombine in the emission layer to generate excitons. The light emission property is realized as excitons transition from excited states and decay to the ground state, thereby emitting light from the emission layer.

[0005] The emitting layer may include a host material and a dopant material to achieve the above-mentioned light emission mechanism. Summary of the Invention

[0006] One or more aspects of embodiments of this disclosure relate to a condensed heterocyclic compound having improved spectral and luminescent properties.

[0007] One or more aspects of embodiments of this disclosure relate to a light-emitting device having improved light-emitting properties and reliability.

[0008] One or more aspects of embodiments of this disclosure relate to an electronic device including a light-emitting device.

[0009] 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 disclosed embodiments.

[0010] According to one or more embodiments of this disclosure, a condensed heterocyclic compound represented by chemical formula 1 is provided.

[0011] Chemical Formula 1

[0012] In chemical formula 1, X1 and X2 can each be independently O, S or Se.

[0013] R1 and R2 can both be independently represented by groups of chemical formula 2.

[0014] Chemical formula 2

[0015] In chemical formulas 1 and 2, R3 to R 10 Each group can be independently hydrogen, deuterium, halogen, hydroxyl, cyano, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C3-C 60 Heterocyclic alkyl, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C8-C 60 Condensed polycyclic groups, -SiRR'R'', -P(=O)RR', -NRR', -BRR', -C(=O)R or -S(=O)2R; and optionally selected from R3 to R 10 Two or more of them combine with each other to form substituted or unsubstituted C3-C 60 Cycloalkyl ring, substituted or unsubstituted C5-C 60 Cycloalkenyl ring, substituted or unsubstituted C3-C 60 Heterocyclic alkyl rings, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl rings, substituted or unsubstituted C6-C 60 The aryl ring may be substituted or unsubstituted C2-C 60 Mixed aromatic rings.

[0016] R, R', and R'' can each be independently hydrogen, deuterium, halogen, hydroxyl, cyano, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C60 Alkoxy, substituted or unsubstituted C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C3-C 60 Heterocyclic alkyl, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthioyl or substituted or unsubstituted C8-C 60 Condensation polycyclic groups.

[0017] n, q, and s can each be an independent integer from 0 to 3, m and p can each be an independent integer from 0 to 4, r can be an integer from 0 to 2, and t and u can each be an independent integer from 0 to 5. When n, m, p, q, r, s, t, and u are all 2 or greater, the integers are selected from the corresponding R3 to R 10 Two or more of them can be independently the same as or different from each other. Indicates the junction point.

[0018] In one or more embodiments, the group represented by chemical formula 2 may be represented by chemical formula 2-1 or chemical formula 2-2.

[0019] Chemical formula 2-1

[0020] Chemical formula 2-2

[0021] In chemical formulas 2-1 and 2-2, R8 and R... 10 , s and u can each independently interact with R8 and R as defined in chemical formula 2. 10 , s and u are the same. R 11 and R 12 Each group can be independently hydrogen, deuterium, halogen, cyano, hydroxyl, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C3-C 60 Heterocyclic alkyl, substituted or unsubstituted C3-C60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C8-C 60 Condensed polycyclic groups, -SiRR'R", -P(=O)RR', -NRR', -BRR', -C(=O)R or -S(=O)2R.

[0022] R, R', and R'' can all be independently identical to R, R', and R'' as defined in Chemical Formula 1 and Chemical Formula 2.

[0023] v and w can both be independent integers from 0 to 5. When v and w are both 2 or greater, the values ​​are selected from the corresponding R. 11 and R 12 Two or more of them can be independently the same as or different from each other.

[0024] In one or more embodiments, the condensed heterocyclic compound may be represented by chemical formulas 1-1 to 1-11.

[0025] Chemical Formula 1-1

[0026] Chemical formula 1-2

[0027] Chemical formulas 1-3

[0028] Chemical formulas 1-4

[0029] Chemical formulas 1-5

[0030] Chemical formulas 1-6

[0031] Chemical formulas 1-7

[0032] Chemical formulas 1-8

[0033] Chemical formulas 1-9

[0034] Chemical formulas 1-10

[0035] Chemical formula 1-11

[0036] In chemical formulas 1-1 to 1-11, X1, X2, and R1 to R6 can all be independently identical to X1, X2, and R1 to R6 as defined in chemical formulas 1 and 2. 31 To R 33 All can be as described in R3, R 41 To R 44 All can be as described in R4, R 51 To R 54 All can be as described in R5, R 61 To R 63 All can be as described in R6, R 71 and T 72 All can be as described with reference to R7. In chemical formulas 1-1 to 1-11, m' can be 0 to 2, n' can be 0 or 1, p' can be 0 to 2, and q' can be 0 or 1. When both m' and p' are 2, the two selected from the corresponding R4 and R5 can be independently the same or different from each other. In chemical formulas 1-1 to 1-11, Y1 can be C(Z1) or N, Y2 can be C(Z2) or N, Y3 can be C(Z3) or N, Y4 can be C(Z4) or N, Y5 can be C(Z5) or N, Y6 can be C(Z6) or N, Y7 can be C(Z7) or N, Y8 can be C(Z8) or N, Y9 can be C(Z9) or N, Y 10 It can be C(Z) 10 ) or N, Y 11 It can be C(Z) 11 ) or N, Y 12 It can be C(Z) 12 ) or N, T1 to T4 can all be independent single bonds, O, S or Se, and Z1 to Z 12 All can be as described in reference R3.

[0037] In one or more embodiments, in Formula 1, at least two of the R3 to R6 may be the same.

[0038] In one or more embodiments, in chemical formula 1 and chemical formula 2, R3 to R 10 Each can be independently hydrogen, deuterium, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C6-C 20 aryl or substituted or unsubstituted C2-C15 Mixed aromatic compounds.

[0039] In one or more embodiments, in Formula 1, n, m, p and q can each be independently 0 to 2.

[0040] In one or more embodiments, in chemical formula 2, s, t, and u can each be 0 or 1 independently.

[0041] In one or more embodiments, in chemical formula 1 and chemical formula 2, R3 to R 10 They can all be independently hydrogen, deuterium, or C4-C atoms substituted with or unsubstituted deuterium. 15 Tertiary alkyl groups, substituted or unsubstituted phenyl groups, substituted or unsubstituted C7-C groups 20 Alkylphenyl, biphenyl substituted with or unsubstituted with deuterium, terphenyl substituted with or unsubstituted with deuterium, naphthyl substituted with or unsubstituted with deuterium, carbazolyl substituted with or unsubstituted with deuterium, dibenzofuranyl substituted with or unsubstituted with deuterium, or pyridyl substituted with or unsubstituted with deuterium.

[0042] In one or more embodiments, the condensed heterocyclic compound may be any of the compounds represented by the chemical formulas as explained herein.

[0043] According to one or more embodiments of this disclosure, the light-emitting device may include: a first electrode; a second electrode; and an intermediate layer between the first electrode and the second electrode. The intermediate layer may include an emitting layer, which may include a condensed heterocyclic compound represented by Formula 1.

[0044] In one or more embodiments, the emission layer may include a host and a dopant, and the condensed heterocyclic compound may be included as a thermally activated delayed fluorescence (TADF) dopant.

[0045] In one or more embodiments, the dopant may also include a phosphorescent dopant.

[0046] In one or more embodiments, the subject may include a hole transport subject represented by the chemical formula HT, which will be explained later, and an electron transport subject represented by the chemical formula ET, which will be explained later.

[0047] In one or more embodiments, the intermediate layer may further include: a hole transport layer between the emitter layer and the first electrode; and an electron transport layer between the emitter layer and the second electrode.

[0048] In one or more embodiments, the intermediate layer may further include: an electron blocking layer between the hole transport layer and the emitter layer; and a hole blocking layer between the emitter layer and the electron transport layer.

[0049] In one or more embodiments, the hole transport layer or electron blocking layer may include a compound represented by the chemical formula HT.

[0050] In one or more embodiments, the electron transport layer or hole blocking layer may include a compound represented by the chemical formula ET.

[0051] In one or more embodiments, the emitting layer may emit green light, and the maximum emission wavelength of the green light (e.g., the wavelength at the maximum emission intensity or peak emission wavelength) may be in the range of about 510 nanometers (nm) to about 540 nm.

[0052] According to one or more embodiments of this disclosure, an electronic device including a light-emitting device is provided.

[0053] Electronic devices can be at least one of the following: flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, indoor lights, outdoor lights, signal lights, head-up displays, fully transparent displays, partially transparent displays, flexible displays, rollable displays, foldable displays, stretchable displays, laser printers, telephones, mobile phones, tablet computers, tablet phones, personal information terminals (PDAs), wearable devices, laptop computers, digital cameras, camcorders, viewfinders, microdisplays, 3D displays, virtual reality displays, augmented reality displays, vehicles, video walls including multiple displays spliced ​​together, theater screens, stadium screens, light therapy devices, and signs.

[0054] The condensed heterocyclic compound according to one or more disclosed embodiments includes a core of a Z-shaped condensed ring structure as a multi-resonant region. Therefore, the condensed heterocyclic compound can form a HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) crossover region, and thus can provide improved optical properties.

[0055] Condensed heterocyclic compounds may include boron atoms bonded to the central benzene ring at the para position and nitrogen and chalcogenide atoms bonded to the para position in the multi-resonance region. Multiple resonances in this multi-resonance region can be weakened, and thus portions may be generated where HOMOs or LUMOs are adjacent to each other.

[0056] Condensed heterocyclic compounds can include a terphenyl moiety bound to a nitrogen atom. Therefore, the Dexter energy transfer (DET) phenomenon can be suppressed or reduced, and the planarity of the molecule can be reduced to increase intermolecular distance, thereby reducing intermolecular interactions and protecting the p orbitals of boron.

[0057] Therefore, condensed heterocyclic compounds can possess low HOMO energy levels and thus exhibit improved luminous efficiency. Low HOMO energy levels are achieved by lowering the energy barrier for hole injection, thereby enhancing the overall efficiency of the light-emitting device. Improved luminous efficiency means that the device can produce brighter light with less power consumption, making it more energy-efficient and cost-effective. This characteristic is beneficial for applications in display technologies that demand high brightness and low power consumption to extend battery life and provide a better user experience.

[0058] Condensed heterocyclic compounds can possess a three-dimensional, bulky chemical structure, thereby increasing the distance from the host and reducing side reactions caused by intermolecular interactions. This bulky structure minimizes or reduces the likelihood of aggregation and quenching, which could degrade the performance of light-emitting devices. By maintaining greater distances between molecules, the compound ensures stable and consistent light emission. Therefore, light-emitting devices with improved lifetime properties can be realized by incorporating condensed heterocyclic compounds.

[0059] Condensed heterocyclic compounds possess a balanced chemical structure with respect to chalcogenides, enabling the development of light-emitting devices with improved luminous efficiency and lifetime properties through the inclusion of such compounds. This balanced chemical structure enhances the interaction between the chalcogenide and other components of the compound, resulting in enhanced charge transport and light emission properties. This balance contributes to the overall stability and luminous efficiency of the light-emitting device, making it suitable for high-performance applications such as OLED displays and lighting systems. Furthermore, the inclusion of chalcogenides can provide unique optical properties, such as specific emission wavelengths and improved color purity, further enhancing device performance. Attached Figure Description

[0060] The accompanying drawings are included to provide a further understanding of this disclosure, and are incorporated in and constitute a part of this disclosure. The drawings illustrate embodiments of the disclosure and, together with the specification, serve to explain the principles of the disclosure. The above and / or other aspects of the disclosure should become apparent and understood from the following description of embodiments taken in conjunction with the accompanying drawings.

[0061] Figures 1 through 6 are schematic cross-sectional views illustrating a light-emitting device according to one or more embodiments of the present disclosure.

[0062] Figure 7 is a schematic cross-sectional view illustrating a display device according to one or more embodiments of the present disclosure.

[0063] Figure 8 is a schematic cross-sectional view illustrating a display device according to one or more embodiments of the present disclosure.

[0064] Figure 9 is a schematic cross-sectional view showing a stacked configuration of light-emitting structures in a display device according to one or more embodiments of the present disclosure.

[0065] Figure 10 is a schematic cross-sectional view illustrating a display device according to one or more embodiments of the present disclosure.

[0066] Figure 11 is a schematic cross-sectional view showing a display device according to one or more embodiments of the present disclosure.

[0067] Figure 12 is a block diagram of an electronic device according to one or more embodiments of the present disclosure.

[0068] Figure 13 is a schematic diagram illustrating an electronic device according to various embodiments of the present disclosure.

[0069] Figure 14 is a schematic exploded perspective view illustrating an electronic device according to one or more embodiments of the present disclosure.

[0070] Figure 15 is a schematic cross-sectional view illustrating an electronic device according to one or more embodiments of the present disclosure. Detailed Implementation

[0071] According to this disclosure, the condensed heterocyclic compound includes a terphenyl structure bonded to nitrogen atoms forming the condensed ring. Furthermore, light-emitting devices and electronic devices incorporating this condensed heterocyclic compound are provided.

[0072] Definition of Terms In this disclosure, the term "substituted or unsubstituted" may mean unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, halogen, cyano, nitro, amino (or amine), silyl, oxy, thio, sulfinyl, sulfonyl, carbonyl, ester, boron, phosphine oxide, phosphine sulfide, alkyl (e.g., C1-C1), halogen, cyano, phosphine sulfide, alkyl (e.g., C1-C1), alkyl group. 60 Alkyl, C1-C 10 Alkyl), alkenyl (e.g., C2-C) 60 alkenyl, C2-C 10 alkenyl), alkynyl (e.g., C2-C) 60 alkynyl group, C2-C 10 alkynyl), alkoxy (e.g., C1-C) 60 Alkoxy, C1-C 10 alkoxy), hydrocarbon cycloyl, aryl (e.g., C6-C) 60 Aryl) and heterocyclic groups (e.g., C1-C) 60 Heterocyclic groups). For example, the term "substituted alkyl" can refer to a group in which at least one of the hydrogen atoms of the alkyl group is replaced by the aforementioned substituent and thus the substituent is bonded to the carbon atom of the alkyl group.

[0073] Substituents may include combinations of substituents selected from the above-described groups. For example, at least one hydrogen atom of alkyl and / or aryl groups included as substituents may be replaced by deuterium, halogen, cyano, nitro, amino, silyl, oxy, thio, sulfinyl, sulfonyl, carbonyl, ester, boron, phosphine oxide, phosphine sulfide, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclic, or combinations thereof (e.g., any suitable combination).

[0074] Among the substituents mentioned above, polyvalent substituents (such as amino, phosphine sulfide, phosphine oxide, sulfinyl, sulfonyl, oxy, carbonyl, and / or ester groups) can all independently be substituted with C1-C2. 10 Alkyl, C2-C 10 alkenyl, C2-C 10 alkynyl and / or C6-C 10 Aryl.

[0075] In the publication, regarding the term "substituted or unsubstituted C" a -C b "Y group", the range from a to b refers to the number of carbon atoms in the unsubstituted Y group, and may exclude (for example, may exclude) the number of carbon atoms of its substituents.

[0076] In the disclosure, an alkyl group can be a monovalent hydrocarbon group in which a hydrogen atom has been removed from a straight-chain or branched hydrocarbon group. Non-limiting examples of alkyl groups may include methyl, ethyl, propyl, sec-butyl, tert-butyl, isobutyl, pentyl, neopentyl, 2-ethylbutyl, 3,3-dimethylbutyl, hexyl, heptyl, and / or octyl, etc.

[0077] In the disclosure, an alkylene group can be a divalent hydrocarbon group in which two hydrogen atoms have been removed from a straight-chain or branched hydrocarbon group.

[0078] In the disclosure, the alkenyl group may have a skeleton substantially the same as that of the alkyl group and may be a monovalent hydrocarbon group including at least one carbon-carbon double bond. In the disclosure, the alkenyl group may be a divalent hydrocarbon group in which a hydrogen atom is further removed from the alkenyl group.

[0079] In the disclosure, the alkynyl group may have a skeleton substantially the same as that of the alkyl group and may be a monovalent hydrocarbon group including at least one carbon-carbon triple bond. In the disclosure, the alkynyl group may be a divalent hydrocarbon group in which a hydrogen atom is further removed from the alkynyl group.

[0080] In the disclosure, an aryl group can be a monovalent hydrocarbon group in which a hydrogen atom is removed from a hydrocarbon group having an aromatic structure. The definition of an aryl group can also encompass groups in which multiple aromatic rings are directly linked (such as biphenyl). Non-limiting examples of aryl groups can include, for example, phenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, fluorenyl, tetraphenyl, biphenyl, terphenyl, tetraphenyl and / or alkyl, etc.

[0081] In the disclosure, groups in which two or more aryl rings are condensed together or linked together by aliphatic hydrocarbon rings (such as fluorenyl) may be included in the definition of aryl.

[0082] For example, biphenyl can be interpreted as aryl, or as a phenyl group that has been substituted with a phenyl group.

[0083] In the disclosure, the aryl group can be a divalent hydrocarbon group in which a hydrogen atom is further removed from the aryl group.

[0084] In the disclosure, a heteroaryl group can be a monovalent group having an aromatic structure comprising at least one heteroatom (such as B, O, P, S, and / or Si) as a cyclic atom. In the disclosure, a heteroaryl group can be a divalent group having an aromatic structure comprising at least one heteroatom (such as B, O, P, S, and / or Si) as a cyclic atom. When a heteroaryl or heteroaryl group comprises two or more heteroatoms, the two or more heteroatoms may be the same as or different from each other.

[0085] In the disclosure, groups in which two or more aryl rings are condensed or attached to non-aromatic heterocyclic rings (such as carbazole groups) may also be included in the definition of heteroaryl.

[0086] In the publication, the term "cyclic group" can encompass monocyclic or polycyclic groups, and can also encompass aliphatic or aromatic rings.

[0087] In this publication, the term "polycyclic group" can refer to a group in which two or more rings are connected or condensed together by one or more atoms. For example, polycyclic structures can include bicyclic structures, spiro structures, and / or fused structures via bridging carbons.

[0088] In this disclosure, the terms "condensation group" or "condensation ring structure" can both refer to a group in which two or more adjacent rings in the aforementioned polycyclic structure share two or more atoms. Non-limiting examples of condensation ring structures may include naphthalene, anthracene, phenanthrene, fluorene, pyrene, benzo[a]pyrene, pentanebenzene, polyacene, and / or helicene, etc.

[0089] In the disclosure, the terms "cycloalkyl" and "cycloalkenyl" refer, respectively, to saturated and unsaturated cyclic groups in which the cyclic atoms include carbon (e.g., composed of carbon atoms). Heterocyclic groups (e.g., C1-C...) 60 Heterocyclic groups can be cyclic groups that include heteroatoms as cyclic atoms in addition to carbon.

[0090] Each of the cycloalkyl, cycloalkenyl, and heterocyclic groups can be a monocyclic group comprising one (exactly one) ring (e.g., consisting of one (exactly one) ring) or a polycyclic group in which two or more rings are condensed together.

[0091] According to one or more embodiments, a condensed heterocyclic compound represented by chemical formula 1 is provided.

[0092] Chemical Formula 1

[0093] In chemical formula 1, X1 and X2 can each be independently O, S, or Se. In one or more embodiments, X1 and X2 can be the same as or different from each other.

[0094] In one or more embodiments, X1 and X2 can both be 0. In one or more embodiments, X1 and X2 can both be S. In one or more embodiments, X1 and X2 can both be Se. In one or more embodiments, X1 can be 0, and X2 can be S. In one or more embodiments, X1 can be 0, and X2 can be Se. In one or more embodiments, X1 can be S, and X2 can be 0. In one or more embodiments, X1 can be S, and X2 can be Se. In one or more embodiments, X1 can be Se, and X2 can be 0. In one or more embodiments, X1 can be Se, and X2 can be S.

[0095] R1 and R2 can both be independently represented by groups of chemical formula 2.

[0096] Chemical formula 2

[0097] In chemical formulas 1 and 2, R3 to R 10 Each group can be independently hydrogen, deuterium, halogen, hydroxyl, cyano, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C3-C 60 Heterocyclic alkyl, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C2-C 60heteroaryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C8-C 60 Condensed polycyclic groups, -SiRR'R'', -P(=O)RR', -NRR', -BRR', -C(=O)R or -S(=O)2R.

[0098] In one or more embodiments, R3 to R 10 Each group can be independently hydrogen, deuterium, halogen, hydroxyl, cyano, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 20 Alkyl, substituted or unsubstituted C2-C 20 alkenyl, substituted or unsubstituted C2-C 20 Alkyne, substituted or unsubstituted C1-C 20 Alkoxy, substituted or unsubstituted C3-C 40 Cycloalkyl, substituted or unsubstituted C5-C 40 Cycloalkenyl, substituted or unsubstituted C3-C 40 Heterocyclic alkyl, substituted or unsubstituted C3-C 40 Heterocyclic alkenyl, substituted or unsubstituted C6-C 40 aryl, substituted or unsubstituted C2-C 40 heteroaryl, substituted or unsubstituted C6-C 40 aryloxy, substituted or unsubstituted C6-C 40 Arylthio, substituted or unsubstituted C8-C 40 Condensed polycyclic groups, -SiRR'R'', -P(=O)RR', -NRR', -BRR', -C(=O)R or -S(=O)2R.

[0099] In one or more embodiments, R3 to R 10 Each group can be independently hydrogen, deuterium, cyano, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C2-C 10 alkenyl, substituted or unsubstituted C2-C 10 Alkyne, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C3-C 20 Cycloalkyl, substituted or unsubstituted C5-C 20 Cycloalkenyl, substituted or unsubstituted C3-C 20 Heterocyclic alkyl, substituted or unsubstituted C3-C 20 Heterocyclic alkenyl, substituted or unsubstituted C6-C 20 aryl, substituted or unsubstituted C2-C 20heteroaryl, substituted or unsubstituted C6-C 20 aryloxy, substituted or unsubstituted C6-C 20 Arylthio, substituted or unsubstituted C8-C 20 Condensed polycyclic groups, -SiRR'R'' or -NRR'.

[0100] R, R', and R'' can each be independently hydrogen, deuterium, halogen, hydroxyl, cyano, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C3-C 60 Heterocyclic alkyl, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthioyl or substituted or unsubstituted C8-C 60 Condensation polycyclic groups.

[0101] In one or more embodiments, R3 to R 10 They can all be independently hydrogen, deuterium, or C4-C atoms substituted with or unsubstituted deuterium. 15 Tertiary alkyl groups (e.g., substituted or unsubstituted tertiary butyl groups), substituted or unsubstituted phenyl groups, substituted or unsubstituted C7-C groups. 20 Alkylphenyl (e.g., substituted or unsubstituted methylphenyl, substituted or unsubstituted di-tert-butylphenyl and / or substituted or unsubstituted trimethylphenyl, etc.), substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted pyridyl.

[0102] In one or more embodiments, R3 to R 10 They can all be independently hydrogen, deuterium, amidine, hydrazine, hydrazone, or C1-C. 10Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornel-enyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, tetrahydronaphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, phenyl, pyrrole, thiophene, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindole, indole, inzolyl, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, Phthalatazinyl, naphthidyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, cenylinyl, carbazole, phenanthridine, acridineyl, phenanthroxolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiopheneyl, benzoisothiazolyl, benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, dibenzofuranyl, dibenzothiopheneyl, benzocarbazole, dibenzocarbazole, imidazopyridyl, imidazopyrimidinyl, azacarbazole, azadibenzofuranyl, azadibenzothiopheneyl, azafluorenyl, or azadibenzothiopheneyl. These may be unsubstituted or substituted with the above-mentioned substituents.

[0103] In one or more embodiments, R3 to R 10 Each can be independently hydrogen, deuterium, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C6-C 20 aryl or substituted or unsubstituted C2-C 15 Heteroaryl. For example, in one or more embodiments, R3 to R 10 Each can independently replace deuterium-containing C6-C. 20 aryl or unsubstituted C6-C 20 Aryl or deuterated C2-C 15 heteroaryl or unsubstituted C2-C 15 Mixed aromatic compounds.

[0104] Therefore, condensed heterocyclic compounds can essentially comprise aryl structures (e.g., composed of aryl structures), and the resonant and electron transport properties of condensed heterocyclic compounds can be improved. Additionally, the external reaction sites of condensed heterocyclic compounds undergoing luminescent transitions can be protected, and side reactions (e.g., Dexter energy transfer) can be suppressed or reduced.

[0105] In chemical formulas 1 and 2, the derivatives are selected from R3 to R4. 10 Two or more of them can combine with each other to form a ring. R3 to R 10 The remaining portions that do not form a ring may be selected from those listed groups.

[0106] In one or more embodiments, the components selected from R3 to R 10Two or more of them can combine with each other to form substituted or unsubstituted C3-C 60 Cycloalkyl ring, substituted or unsubstituted C5-C 60 Cycloalkenyl ring, substituted or unsubstituted C3-C 60 Heterocyclic alkyl rings, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl rings, substituted or unsubstituted C6-C 60 The aryl ring may be substituted or unsubstituted C2-C 60 Mixed aromatic rings.

[0107] In one or more embodiments, the components selected from R3 to R 10 Two or more of them can combine with each other to form substituted or unsubstituted C3-C 40 Cycloalkyl ring, substituted or unsubstituted C5-C 40 Cycloalkenyl ring, substituted or unsubstituted C3-C 40 Heterocyclic alkyl rings, substituted or unsubstituted C3-C 40 Heterocyclic alkenyl rings, substituted or unsubstituted C6-C 40 The aryl ring may be substituted or unsubstituted C2-C 40 Heteroary aromatic rings. For example, in one or more embodiments, if (e.g., when) selected from R3 to R 10 When two or more of them combine to form a ring, substituted or unsubstituted C2-C can be formed. 40 Condensed heteroaryl ring.

[0108] In one or more embodiments, if (e.g., when) R3 to R 10 When each of the groups exists in a plural form, adjacent groups may optionally combine to form a ring, or non-adjacent groups may optionally combine to form a ring.

[0109] For example, if (for example, when) R3 exists in a complex number, then multiple R3s can optionally be combined to form a ring. If (for example, when) R4 exists in a complex number, then multiple R4s can optionally be combined to form a ring. If (for example, when) R5 exists in a complex number, then multiple R5s can optionally be combined to form a ring.

[0110] For example, R4 and R5 can be combined to form a ring.

[0111] In Chemical Formula 1 and Chemical Formula 2, n, q, and s can each be independently 0 or an integer from 1 to 3. For example, in one or more embodiments, n, q, and s can each be independently 0, 1, or 2.

[0112] When each of n, q, and s is 2 or greater, multiple R3s, multiple R6s, and multiple R8s can all be independently identical or different from each other.

[0113] In Formula 1, m and p can each be independently 0 or an integer from 1 to 4. For example, in one or more embodiments, m and p can each be independently 0, 1, or 2.

[0114] When both m and p are 2 or greater, two or more selected from the corresponding R4 and R5 can be independently the same or different from each other.

[0115] In chemical formula 1, r can be 0, 1, or 2. For example, in one or more embodiments, r can be 0 or 1.

[0116] When r is 2, multiple R7s can be the same or different from each other.

[0117] In chemical formula 2, t and u can both be independent integers from 0 to 5. For example, in one or more embodiments, t and u can both be independent 0 or 1.

[0118] When both t and u are 2 or greater, the corresponding R9 and R are selected. 10 Two or more of them can be independently the same as or different from each other.

[0119] In chemical formula 2, The term refers to the associative position, and it can also be used to refer to the associative position in the following description.

[0120] In one or more embodiments, the components selected from R3 to R 10 At least one of them can be deuterium.

[0121] In one or more embodiments, the group represented by chemical formula 2 may be represented by chemical formula 2-1 or chemical formula 2-2.

[0122] Chemical formula 2-1

[0123] Chemical formula 2-2

[0124] In chemical formulas 2-1 and 2-2, R8 and R can also be applied. 10 The above definitions apply to s and u.

[0125] In chemical formulas 2-1 and 2-2, R 11 and R 12 Each group can be independently hydrogen, deuterium, halogen, cyano, hydroxyl, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C3-C 60 Heterocyclic alkyl, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C8-C 60 Condensed polycyclic groups, -SiRR'R", -P(=O)RR', -NRR', -BRR', -C(=O)R, or -S(=O)2R. The above definitions of R, R', and R" can also be applied.

[0126] v and w can each be independently 0 to 5. For example, in one or more embodiments, v and w can each be independently 0 or 1.

[0127] When both v and w are 2 or greater, the value is selected from the corresponding R. 11 and R 12 Two or more of them can be independently the same as or different from each other.

[0128] The condensed heterocyclic compound according to one or more embodiments can be represented by chemical formulas 1-1 to 1-11.

[0129] Chemical Formula 1-1

[0130] Chemical formula 1-2

[0131] Chemical formulas 1-3

[0132] Chemical formulas 1-4

[0133] Chemical formulas 1-5

[0134] Chemical formulas 1-6

[0135] Chemical formulas 1-7

[0136] Chemical formulas 1-8

[0137] Chemical formulas 1-9

[0138] Chemical formulas 1-10

[0139] Chemical formula 1-11

[0140] In chemical formulas 1-1 to 1-11, the above definitions of X1, X2, and R1 to R6 can also be applied, R 31 To R 33 All can be as described in R3, R 41 To R 44 All can be as described in R4, R 51 To R 54 All can be as described in R5, R 61 To R 63 All can be as described in R6, R 71 and T 72 All can be as described in R7.

[0141] In chemical formulas 1-1 to 1-11, m' can be 0 to 2, n' can be 0 or 1, p' can be 0 to 2, and q' can be 0 or 1.

[0142] When both m' and p' are 2, two or more selected from the corresponding R4 and R5 can be independently the same or different from each other.

[0143] In chemical formulas 1-1 to 1-11, Y1 can be C(Z1) or N, Y2 can be C(Z2) or N, Y3 can be C(Z3) or N, Y4 can be C(Z4) or N, Y5 can be C(Z5) or N, Y6 can be C(Z6) or N, Y7 can be C(Z7) or N, Y8 can be C(Z8) or N, Y9 can be C(Z9) or N, Y 10 It can be C(Z) 10 ) or N, Y 11 It can be C(Z) 11 ) or N, Y 12 It can be C(Z) 12 ) or N, T1 to T4 can all be independent single bonds, O, S or Se, and Z1 to Z 12 All can be as described in reference R3.

[0144] In one or more embodiments, in Formula 1, at least two of the R3 to R6 may be the same. In one or more embodiments, at least three of the R3 to R6 may be the same.

[0145] In one or more embodiments, in Formula 1, at least two of R3 to R6 can each be independently hydrogen, deuterium, or a C4-C substituted with deuterium or unsubstituted. 15 Tertiary alkyl groups (e.g., substituted or unsubstituted tertiary butyl groups), substituted or unsubstituted phenyl groups, substituted or unsubstituted C7-C groups. 20 Alkylphenyl (e.g., substituted or unsubstituted methylphenyl, substituted or unsubstituted di-tert-butylphenyl, substituted or unsubstituted trimethylphenyl), substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted pyridyl.

[0146] The degree of deuterium substitution in the condensed heterocyclic compounds according to one or more embodiments can range from 0% to 100%. The degree of deuterium substitution can be a value calculated as a percentage of the number of deuterium atoms relative to the sum of the number of hydrogen atoms and the number of deuterium atoms included in the compound. For example, the degree of deuterium substitution of benzene with 5 deuterium atoms can be about 83.33%.

[0147] The degree of deuterium substitution of the condensed heterocyclic compound according to one or more embodiments may be in the range of about 1% to 100%, about 5% to 100%, about 20% to 100%, about 30% to 100%, about 40% to 100%, or about 50% to 100%.

[0148] The degree of deuterium substitution of the condensed heterocyclic compound according to one or more embodiments can be in the range of 0% to about 90%, 0% to about 80%, 0% to about 70%, 0% to about 60%, or 0% to about 50%.

[0149] The condensed heterocyclic compound according to one or more embodiments may be selected from any of the compounds represented by the following chemical formulas.

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174] .

[0175] The condensed heterocyclic compound may have a heterocyclic core structure comprising boron, nitrogen, and chalcogenide atoms (such as O and / or S), and may include an o-terphenyl moiety bound to nitrogen. The nitrogen atom includes unshared / lone pairs of electrons, allowing the o-terphenyl to be oriented perpendicular to the luminescent core plane of the condensed heterocyclic compound. Therefore, the distance between the luminescent core plane of the condensed heterocyclic compound and the host can be increased, and side reactions of the boron atom due to intermolecular interactions (e.g., Dexter energy transfer) can be reduced, thereby improving the lifetime properties of the light-emitting device incorporating the condensed heterocyclic compound.

[0176] Additionally, condensed heterocyclic compounds can include two nitrogen atoms and may include an ortho-terphenyl moiety bonded to each of the nitrogen atoms. Therefore, condensed heterocyclic compounds can have a balanced molecular structure, resulting in the prevention or reduction of compound decay due to excitons or polarons.

[0177] In one or more embodiments, condensed heterocyclic compounds may be included as dopants in the emitting layer of the light-emitting device, which will be described in more detail later.

[0178] In light-emitting devices, condensed heterocyclic compounds can be used as dopants that emit green light.

[0179] In one or more embodiments, the maximum emission wavelength of the green light (e.g., the peak emission wavelength) may be in the range of about 500 nm to about 540 nm, about 515 nm to about 555 nm, about 510 nm to about 550 nm, about 520 nm to about 540 nm, or about 520 nm to about 530 nm.

[0180] Figures 1 to 6 are schematic cross-sectional views illustrating light-emitting devices according to one or more embodiments of the present disclosure.

[0181] Referring to FIG1, the light-emitting device ED may include a first electrode 110, a second electrode 150, and an intermediate layer ITL disposed between the first electrode 110 and the second electrode 150. The intermediate layer ITL may include an emitting layer 130. The intermediate layer ITL may also include a hole transport region 120 and an electron transport region 140.

[0182] The first electrode 110 can be an anode or a cathode. In one or more embodiments, the first electrode 110 can be an anode and can be used as a pixel electrode. In these embodiments, the first electrode 110 can include a conductive material having a high work function that promotes hole injection.

[0183] In one or more embodiments, the first electrode 110 may be a transmission electrode. The first electrode 110 may include a transparent conductive oxide such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO) and / or indium tin zinc oxide (ITZO).

[0184] In one or more embodiments, the first electrode 110 may be a translucent electrode or a reflective electrode. The first electrode 110 may include at least one material selected from the following: silver (Ag), magnesium (Mg), copper (Cu), aluminum (Al), platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), neodymium (Nd), iridium (Ir), chromium (Cr), lithium (Li), calcium (Ca), lithium fluoride (LiF), molybdenum (Mo), titanium (Ti), tungsten (W), indium (In), tin (Sn), zinc (Zn), and alloys comprising at least two of these. For example, in one or more embodiments, the first electrode 110 may include Li, Ca, LiF / Ca (a stacked structure of LiF and Ca), LiF / Al (a stacked structure of LiF and Al), and / or a mixture of Ag and Mg.

[0185] The first electrode 110 may have a single-layer structure or a multi-layer structure. For example, in one or more embodiments, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO.

[0186] The thickness of the first electrode 110 can be in the range of about 700 angstroms (Å) to about 10,000 Å. For example, in one or more embodiments, the thickness of the first electrode 110 can be in the range of about 1,000 Å to about 3,000 Å.

[0187] The second electrode 150 can be a cathode or an anode. In one or more embodiments, the second electrode 150 can be used as an electron injection electrode or as a cathode. The second electrode 150 can include metals, alloys, and / or conductive compounds with low work function.

[0188] For example, in one or more embodiments, the second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, and / or IZO, etc. The second electrode 150 may include one of the foregoing materials or a combination thereof (e.g., any suitable combination).

[0189] The second electrode 150 can be a transmission electrode, a semi-transparent electrode, or a reflection electrode. The second electrode 150 can have a single-layer structure or a multi-layer structure.

[0190] The emitting layer 130 may include the aforementioned condensed heterocyclic compound. In one or more embodiments, the condensed heterocyclic compound may be used as a fluorescent dopant. For example, in one or more embodiments, the condensed heterocyclic compound may be used as a thermally activated delayed fluorescence (TADF) dopant.

[0191] In one or more embodiments, a condensed heterocyclic compound may be included as a green-emitting dopant. For example, a condensed heterocyclic compound may be included as a luminescent material having a maximum emission wavelength in the range of about 520 nm to about 540 nm.

[0192] In one or more embodiments, the emitter layer 130 may also include a dopant represented by the chemical formula FD. For example, a compound represented by the chemical formula FD can be used as a fluorescent dopant.

[0193] Chemical formula FD

[0194] In the chemical formula FD, Ar FD R FD1 and R FD2 Each can be independently substituted or unsubstituted C3-C. 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic base. Ax can be an integer from 1 to 6.

[0195] In one or more embodiments, Ar FD It may include condensed ring structures in which three or more aryl rings or benzene rings are condensed together (e.g., anthracene group, β group and / or pyrene group, etc.).

[0196] In one or more embodiments, the emitting layer 130 may include a phosphorescent dopant. The phosphorescent dopant may include an organometallic compound comprising a central metal and at least one ligand bound to the central metal via a coordination bond. The central metal may include, for example, a transition metal, and the ligand may include, for example, monodentate, bidentate, tripentate, tetradentate, pentadentate, hexadentate, and / or combinations thereof (e.g., any suitable combination).

[0197] In one or more embodiments, the phosphorescent dopant may include, for example, a compound represented by the chemical formula PD.

[0198] Chemical formula PDM(L) d 1 ) dx1 (L d 2 ) dx2In the chemical formula PD, M can be a transition metal, such as iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), ruthenium (Ru), copper (Cu), or thulium (Tm).

[0199] In the chemical formula PD, L d 1 It can be a ligand represented by the chemical formula LD1.

[0200] Chemical formula LD1

[0201] In the chemical formula LD1, X PD1 and X PD2 Each can be either C or N independently.

[0202] In one or more embodiments, X PD1 and X PD2 One of them can be C and the other can be N. In one or more embodiments, X PD1 and X PD2 Both can be N.

[0203] In the chemical formula LD1, CG PD1 and CG PD2 Each can be independently substituted or unsubstituted C3-C. 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic group.

[0204] For example, CG PD1 and CG PD2 These groups can all be independently pyrrole groups, pyrazole groups, imidazole groups, triazole groups, oxazole groups, isoxazole groups, thiazole groups, isothiazole groups, oxadiazole groups, thiadiazole groups, phenyl groups, pyridine groups, pyrimidine groups, naphthyl groups, dibenzofuran groups, dibenzothiophene groups, carbazole groups, fluorene groups, dibenzothiophene groups, naphthenofuran groups, naphthenophene groups, benzocarbazole groups, benzofluorene groups, naphthenofuran groups, dinaphthofuran groups, dinaphthothiophene groups. Group, dibenzocarbazole group, dibenzofluorene group, dinaphthothiophene group, azidobenzofuran group, azidobenzothiophene group, azidocarbazole group, azidofluorene group, azidobenzothiophene group, azidobenzobenzofuran group, azidobenzobenzothiophene group, azidobenzocarbazole group, azidobenzofluorene group, azidobenzobenzothiophene group, azidobenzofuran group, azidobenzothiophene group, azidobenzocarbazole group, azidobenzofluorene group or azidobenzothiophene group.

[0205] In the chemical formula LD1, L PD It can be a single bond, a substituted or unsubstituted methylene, a substituted or unsubstituted ethylene, -O- '、 -S- '、 -C(=O)- '、 -N(R PD3 )- '、 -C(R PD4 )= 'or =C(R PD5 )- '.

[0206] In the chemical formula LD1, X PD3 and X PD4 Each can be an independent chemical bond, O, S, N (R) PD6 ), B(R) PD7 ), P(R PD8 ), C(R PD8 (R) PD9 ) or Si(R PD10 (R) PD11 Chemical bonds can be, for example, covalent bonds or coordinate bonds.

[0207] In the chemical formula LD1, R PD1 and R PD2 They can all be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -OH, -CN, -NO2, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C3-C 60 Heterocyclic alkyl, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C8-C 60Condensed polycyclic groups, substituted or unsubstituted silyl groups, substituted or unsubstituted amino groups, substituted or unsubstituted aniline groups, -B(R) PD12 (R) PD13 -C(=O)(R) PD14 -S(=O)2(R) PD15 ) or -P(=O)(R PD16 (R) PD17 ). Silyl groups can be derived from -Si(R) as explained herein. sa (R) sb (R) sc ) indicates, and R sa R sb and R sc They can all be independently hydrogen, halogen, hydroxyl, C1-C 60 Alkyl, C1-C 60 Alkoxy, C6-C 60 Aryl or C2-C 30 Mixed aromatic compounds.

[0208] R PD3 To R PD17 They can all be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -OH, -CN, -NO2, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C3-C 60 Heterocyclic alkyl, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthioyl or substituted or unsubstituted C8-C 60 Condensation polycyclic groups.

[0209] In the chemical formula LD1, cx1 and cx2 can both be independent integers from 0 to 10. When at least one of cx1 and cx2 is 2 or greater, R... PD1 Two or more of R and / or R PD2 Two or more of them can be the same as or different from each other.

[0210] symbol- and- 'These all indicate that the ligand represented by the chemical formula LD1 binds to the binding site of M.'

[0211] In the chemical formula PD, dx1 can be an integer from 1 to 3. When dx1 is 2 or 3, L d 1 Two or three of them can be the same as or different from each other. In L d 1 Among two or three CGs, those that are adjacent to each other. PD1 and / or CG PD2 Through, such as L PD1 and / or L PD2 Linking groups such as L are connected to each other. PD1 and / or L PD2 The linking groups can all independently bind to L. PD The definitions are the same.

[0212] In the chemical formula PD, L d 2 It can be an organic ligand. L d 2 It may include, for example, halogens, CO, NO, CS, pyridine carboxylates, acetates, oxalates, diketones, isonitriles, isothiocyanates-N, thiosulfates-S, alkylphosphines, phenylphosphines, arylphosphines, phosphine oxides, phosphites, or combinations thereof (e.g., any suitable combination).

[0213] In the chemical formula PD, dx2 is an integer from 0 to 4. When dx2 is 2 or greater, L d 2 Two or more of them can be the same as or different from each other.

[0214] In one or more embodiments, the emitter layer 130 may include a styrene derivative (e.g., 1,4-bis[2-(3-N-ethylcarbazolyl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styrene]benzene (DPAVB) and / or N-(4-((E)-2-(6-(((E)-4-(diphenylamino)styrene)naphth-2-yl)vinyl)phenyl) One or more of the following are used as fluorescent dopant materials: 1,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi), perylene or its derivatives (e.g., 2,5,8,11-tetra-tert-butylperylene (TBP)), and pyrene or its derivatives (e.g., 1,1'-dipyrene, 1,4-dipyrenebenzene and / or 1,4-bis(N,N-diphenylamino)pyrene).

[0215] In one or more embodiments, in addition to one or more of the materials described above, the emitting layer 130 may also include metal complexes comprising iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm) as phosphorescent dopants. For example, FIrpic (bis(4,6-difluorophenylpyridine-N,C2)pyridinecarboxylic acid iridium(III)), FIr6 (bis(2,4-difluorophenylpyridine)-tetra(1-pyrazolyl)boronic acid iridium(III)) and / or PtOEP (octaethylporphyrin platinum) can be used as phosphorescent dopants.

[0216] The aforementioned dopant materials can be used alone or in combination of two or more selected therefrom.

[0217] The emitter layer 130 may include a host material that can interact with the dopants described above. For example, in one or more embodiments, the emitter layer 130 may include a host material that is widely applicable in related technologies, such as anthracene derivatives, pyrene derivatives, fluoranthene derivatives, phenanthrene derivatives, dihydrobenzanthene derivatives, and / or benzo[9,10]phenanthrene derivatives.

[0218] In one or more embodiments, the emitting layer 130 may include a host material, for example, represented by the chemical formula FH. For example, a compound represented by the chemical formula FH may be used as a fluorescent host material.

[0219] Chemical formula FH

[0220] In the chemical formula FH, R FH1 To R FH4 Each of these can be independently hydrogen, deuterium, halogen, substituted or unsubstituted silyl group, substituted or unsubstituted thio group, substituted or unsubstituted oxy group, or substituted or unsubstituted C1-C group. 10 Alkyl, substituted or unsubstituted C2-C 10 alkenyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C6-C 30 Heteroaryl groups or cyclic groups formed by combinations thereof. In one or more embodiments, in the chemical formula FH, the group selected from R... FH1 To R FH4 At least one of them can form a condensation ring with the benzene ring to which it is attached.

[0221] In the chemical formula FH, Ar FH1 and Ar FH2 Both can be independently substituted or unsubstituted C6-C. 30 aryl, substituted or unsubstituted C2-C30 Hypoaryl groups or divalent cyclic groups formed therefrom.

[0222] In the chemical formula FH, x1a and x1b can each be an independent integer from 0 to 5; and x2a and x2b can each be an independent integer from 0 to 4. When x1a, x1b, x2a, and x2b are all 2 or greater, the values ​​are selected from the corresponding R. FH1 To R FH4 Two or more of them can be the same as or different from each other.

[0223] In one or more embodiments, the emitting layer 130 may include a host material, for example, represented by the chemical formula pH. For example, a compound represented by the chemical formula pH may be used as a host material for a light-emitting device (e.g., for use as a phosphorescent dopant).

[0224] Chemical formula pH

[0225] In the chemical formula pH, R PH It can be a substituted or unsubstituted carbazole group. PH It can be a direct-connect key, a replaced or unreplaced C6-C. 30 aryl or substituted or unsubstituted C2-C 30 Hybrid aryl. Ar PH It can be substituted or unsubstituted C6-C 30 aryl or substituted or unsubstituted C2-C 30 Mixed aromatic compounds.

[0226] As described in the definition of the term above, the term "C6-C" 30 "Aryl" can encompass groups in which multiple aryl rings are condensed or linked by cyclic groups (e.g., aliphatic hydrocarbon rings). For example, C6-C 30 Aryl groups can be fluorene groups.

[0227] As described in the definition of the term above, the term "C2-C" 30 "Heteroaryl" can encompass groups in which multiple aryl rings are condensed or linked by heterocyclic rings. For example, C2-C 30 The heteroaryl group can be carbazole, dibenzofuran, and / or dibenzothiophene, etc. In one or more embodiments, C2-C 30 A heteroaryl group can be a group in which multiple aryl rings are condensed or linked together by the same or different heterocyclic rings.

[0228] In one or more embodiments, including Ar PH The substituents in it can be -Si(R) sa (R) sb (R) sc) represents silyl group; and R sa R sb and R sc They can all be independently hydrogen, halogen, hydroxyl, C1-C 60 Alkyl, C1-C 60 Alkoxy, C6-C 60 Aryl or C2-C 30 Mixed aromatic compounds. Selected from R sa R sb and R sc At least one of them can be C6-C 60 Aryl or C2-C 30 Heteroaryl. For example, in one or more embodiments, R sa R sb and R sc They can all be C6-C independently. 60 Aryl or C2-C 30 Mixed aromatic compounds.

[0229] In the chemical formula pH, lx can be an integer from 0 to 10. When lx is 2 or greater, L... PH Two or more of them can be the same as or different from each other.

[0230] In one or more embodiments, the emitter layer 130 may include, for example, BCPDS (bis(4-(9H-carbazole-9-yl)phenyl)diphenylsilane), POPCPA ((4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenylphosphine oxide), DPEPO (bis[2-(diphenylphosphino)phenyl] ether oxide), mCBP (3,3'-bis(9H-carbazole-9-yl)-1,1'-biphenyl), CBP (4,4'-bis(N-carbazole)-1,1'-biphenyl), mCP (1,3-bis(carbazole-9-yl)benzene), PPF (2,8-bis(diphenylphospho)dibenzo[b,d]furan), TCTA (4,4',4''-tris(carbazole-9-yl)triphenyl Amines, TPBi (1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene), Alq3 (tris(8-hydroxyquinoline)aluminum), ADN (9,10-di(naphthyl-2-yl)anthracene), TBADN (2-tert-butyl-9,10-di(naphthyl-2-yl)anthracene), DSA (stilbeneyl arylene), CDBP (4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl), MADN (2-methyl-9,10-bis(naphthyl-2-yl)anthracene), CP1 (hexaphenylcyclotriphosphazene), UGH2 (1,4-bis(triphenylsilyl)benzene), DPSiO3 (hexaphenylcyclotrisiloxane) and / or DPSiO4 (octaphenylcyclotetrasiloxane) are used as main materials.

[0231] In one or more embodiments, the body in the emission layer 130 may include one or any combination of the materials described above.

[0232] In one or more embodiments, the emitter layer 130 may include two or more host materials. For example, in one or more embodiments, the emitter layer 130 may include a hole transport host and an electron transport host. In these embodiments, the emitter layer 130 may include a hole transport host, an electron transport host, a photosensitizer, and a dopant. In one or more embodiments, the hole transport host and the electron transport host may form an excimer complex, and energy can be transferred from the excimer complex to the photosensitizer and from the photosensitizer to the dopant, thereby inducing light emission.

[0233] Non-limiting examples of hole transport entities may include compounds represented by the chemical formula HT.

[0234] Chemical formula HT

[0235] In the chemical formula HT, L HT1 L HT2 and L HT3 Each can be an independent direct bond, substituted or unsubstituted C6-C. 30 aryl or substituted or unsubstituted C2-C 30 Hybrid aryl.

[0236] In the chemical formula HT, lx1 to lx3 can each be an independent integer from 0 to 10. When lx1, lx2, or lx3 is 2 or greater, it is selected from the corresponding L. HT1 L HT2 and L HT3 Two or more of them can be obtained, for example, from the carbon atoms of each aryl ring (e.g., sp). 2 Carbon atoms are directly bonded to form substituted or unsubstituted C6-C atoms. 30 aryl or substituted or unsubstituted C2-C 30 Hybrid aryl. For example, when lx1, lx2, or lx3 is 2 or greater, the corresponding L HT1 L HT2 and L HT3 Two or more of them can pass through the carbon atoms of each aryl ring (such as sp...) 2 Carbon atoms are directly bonded together to form substituted or unsubstituted C6-C bonds. 30 aryl or substituted or unsubstituted C2-C 30 Hybrid aryl. For example, when lx1 is 2 or greater, L HT1 Two or more of them can be obtained by, for example, the carbon atoms of each aryl ring (e.g., sp...).2 Carbon atoms are directly bonded to form substituted or unsubstituted C6-C atoms. 30 aryl or substituted or unsubstituted C2-C 30 Hybrid aryl. When lx2 is 2 or greater, L HT2 Two or more of them can be obtained by, for example, the carbon atoms of each aryl ring (e.g., sp...). 2 Carbon atoms are directly bonded to form substituted or unsubstituted C6-C atoms. 30 aryl or substituted or unsubstituted C2-C 30 Hybrid aryl. When lx3 is 2 or greater, L HT3 Two or more of them can be obtained by, for example, the carbon atoms of each aryl ring (e.g., sp...). 2 Carbon atoms are directly bonded to form substituted or unsubstituted C6-C atoms. 30 aryl or substituted or unsubstituted C2-C 30 Hybrid aryl.

[0237] In the chemical formula HT, Ar HT1 and Ar HT2 Both can be independently substituted or unsubstituted C6-C. 30 aryl or substituted or unsubstituted C2-C 30 Mixed aromatic compounds. Ar HT3 It can be substituted or unsubstituted C6-C 30 Aryl.

[0238] In one or more embodiments, the compound represented by the chemical formula HT may be a monoamine compound. In one or more embodiments, the compound represented by the chemical formula HT may be a compound selected from Ar. HT1 To Ar HT3 At least one of them is a diamine compound that includes an amino group as a substituent.

[0239] In one or more embodiments, the compound represented by the chemical formula HT can be Ar. HT1 and Ar HT2 At least one of the carbazole compounds comprising a substituted or unsubstituted carbazole group or wherein Ar HT1 and Ar HT2 At least one of the fluorene compounds includes a substituted or unsubstituted fluorene group.

[0240] In one or more embodiments, Ar HT1 To Ar HT3 Two adjacent groups can condense together to form a ring.

[0241] In a non-limiting example, the electron transport entity may include a compound represented by the chemical formula ET.

[0242] Chemical formula ET

[0243] In the chemical formula ET, it is selected from X. ET1 To X ET3 At least one of them can be N, X ET1 To X ET3 The remaining parts can all be C(R) independently. ET R ET It can be hydrogen, deuterium, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C6-C 60 aryl or substituted or unsubstituted C2-C 60 Mixed aromatic compounds.

[0244] When selected from X ET1 To X ET3 When one of them is N, compounds represented by the chemical formula ET may include pyridinyl. When selected from X... ET1 To X ET3 When two of them are N, compounds represented by the chemical formula ET can include pyrimidinyl groups. When X ET1 To X ET3 When both are nitrogen atoms, compounds represented by the chemical formula ET can include triazine groups.

[0245] In the chemical formula ET, lx1 to lx3 can each be an independent integer from 0 to 10. ET1 To L ET3 Each can be an independent direct bond, substituted or unsubstituted C6-C. 30 aryl or substituted or unsubstituted C2-C 30 Hybrid aryl.

[0246] When lx1, lx2, or lx3 is 2 or greater, it is selected from the corresponding L. ET1 L ET2 and L ET3 Two or more of them can, for example, pass through the carbon atoms of each aryl ring (e.g., sp). 2 Carbon atoms are directly bonded together to form substituted or unsubstituted C6-C bonds. 30 aryl or substituted or unsubstituted C2-C 30 Hybrid aryl. For example, when lx1, lx2, or lx3 is 2 or larger, the corresponding L... ET1 L ET2 and L ET3 Two or more of them can pass through the carbon atoms of each aryl ring (such as sp...) 2 Carbon atoms are directly bonded together to form substituted or unsubstituted C atoms. 6- C30 aryl or substituted or unsubstituted C2-C 30 Hybrid aryl. For example, when lx1 is 2 or greater, L ET1 Two or more of them can be, for example, through the carbon atoms of each aryl ring (e.g., sp). 2 Carbon atoms are directly bonded together to form substituted or unsubstituted C6-C bonds. 30 aryl or substituted or unsubstituted C2-C 30 Hybrid aryl. When lx2 is 2 or greater, L ET2 Two or more of them can be, for example, through the carbon atoms of each aryl ring (e.g., sp). 2 Carbon atoms are directly bonded together to form substituted or unsubstituted C atoms. 6- C 30 aryl or substituted or unsubstituted C2-C 30 Hybrid aryl. When lx3 is 2 or greater, L ET3 Two or more of them can be, for example, through the carbon atoms of each aryl ring (e.g., sp). 2 Carbon atoms are directly bonded together to form substituted or unsubstituted C atoms. 6- C 30 aryl or substituted or unsubstituted C2-C 30 Hybrid aryl.

[0247] In the chemical formula ET, Ar ET1 To Ar ET3 Each can be independently hydrogen, deuterium, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C6-C 30 aryl or substituted or unsubstituted C2-C 30 Heteroaryl. For example, in one or more embodiments, Ar ET1 To Ar ET3 Each of these can be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted carbazole, a substituted or unsubstituted fluorenyl, or a substituted or unsubstituted silyl group. The silyl group can be composed of -Si(R) as explained above. sa (R) sb (R) sc )express.

[0248] In one or more embodiments, the emitter layer 130 may include quantum dots. Quantum dots may include group II-VI compounds, group III-VI compounds, group I-III-VI compounds, group III-V compounds, group III-II-V compounds, group IV-VI compounds, group IV elements, group IV compounds and / or combinations thereof (e.g., any suitable combinations).

[0249] Quantum dots may include a core comprising the aforementioned compounds and a shell surrounding (e.g., around) the core. The shell may include inorganic oxides or semiconductor compounds. Examples of semiconductor compounds as shells may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSe, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, and / or AlSb, etc.

[0250] In one or more embodiments, the color of light emanating from the quantum dots can be adjusted according to the particle size of the quantum dots. The quantum dots can be blue quantum dots that emit blue light, red quantum dots that emit red light, or green quantum dots that emit green light.

[0251] The hole transport region 120 can be formed between the first electrode 110 and the emitter layer 130. The hole transport region 120 can have a single-layer structure or a multi-layer structure comprising different materials.

[0252] The hole transport region 120 may include a hole injection layer, a hole transport layer and / or an electron blocking layer, and may also include an auxiliary emission layer.

[0253] In one or more embodiments, as shown in FIG2, the hole transport region 120 may include a hole injection layer 122 and a hole transport layer 124 sequentially stacked from the first electrode 110.

[0254] In one or more embodiments, as shown in FIG3, the hole transport region 120 may include a hole injection layer 122, a hole transport layer 124, and an electron blocking layer 126 sequentially stacked from the first electrode 110. The electron blocking layer 126 can block electrons from the electron transport region 140 to the hole transport region 120. Therefore, the generation of excitons in the emission layer 130 can be increased, and the luminescence efficiency can be further enhanced.

[0255] For example, in one or more embodiments, the hole transport region 120 may include the above-described compound represented by the chemical formula HT.

[0256] For example, in one or more embodiments, the hole transport region 120 may include a selection from m-MTDATA (4,4',4''-[tris(3-methylphenyl)phenylamino]triphenylamine), TDATA (4,4',4''-tris(N,N-diphenylamino)triphenylamine), 2-TNATA (4,4',4''-tris[N-(2-naphthyl)-N-phenylamino]triphenylamine), NPB (N,N'-di(naphthyl-1-yl)-N,N'-diphenyl-benzidine), TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine), spiro-TPD, spiro-NPB, DNTPD (N 1 N 1' -([1,1'-biphenyl]-4,4'-diyl)bis(N) 1 -Phenyl-N 4 N 4 The hole transport region 120 may include one or more of the following: 1,4-dimethylbenzene-1,4-diamine (-di-m-tolylphenyl-1,4-diamine), TAPC (4,4'-cyclohexylene-bis[N,N-bis(4-methylphenyl)aniline]), HMTPD (4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl), TCTA (4,4',4''-tris(N-carbazolyl)triphenylamine), PANI / DBSA (polyaniline / dodecylbenzenesulfonic acid), PEDOT / PSS (poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate)), PANI / CSA (polyaniline / camphorsulfonic acid), PANI / PSS (polyaniline / poly(4-styrenesulfonate)), phthalocyanine compounds, carbazole compounds (N-phenylcarbazole and / or polyvinylcarbazole, etc.), and fluorene compounds.

[0257] The aforementioned hole transport material may be included in at least one of the hole injection layer 122, the hole transport layer 124, and the electron blocking layer 126.

[0258] In one or more embodiments, the hole transport region 120 may further include a charge-generating material. The charge-generating material may be a dopant material such as a p-doper, which can improve the conductivity of the hole transport region 120.

[0259] Non-limiting examples of dopant materials may include: metal halide compounds (e.g., metal halides), such as LiF, NaCl, CsF, RbCl, RbI, CuI, and KI; quinone derivatives, such as TCNQ (tetracyanoquinone dimethyl) and / or F4-TCNQ (2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethyl); cyano-containing compounds, such as HAT-CN (dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexanitrile) and / or NDP9 (4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropyl]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile); tungsten oxide (W); and / or molybdenum oxide (Mo); and so on. Hole transport region 120 may include one of the dopant materials described above or a combination thereof (e.g., any suitable combination).

[0260] The thickness of the hole transport region 120 can be in the range of about 100 Å to about 10,000 Å. For example, in one or more embodiments, the thickness of the hole transport region 120 can be in the range of about 100 Å to about 1,500 Å.

[0261] When the hole transport region 120 includes a hole injection layer 122 and / or a hole transport layer 124, the thickness of the hole injection layer 122 may be in the range of about 100 Å to about 9,000 Å, about 100 Å to about 3,000 Å, or about 100 Å to about 1,000 Å. The thickness of the hole transport layer 124 may be in the range of about 50 Å to about 2,000 Å, about 100 Å to about 1,500 Å, about 100 Å to about 1,000 Å, or about 100 Å to about 600 Å.

[0262] Within the aforementioned thickness range, hole transport properties can be enhanced even under low-voltage operation, and the lifetime of the light-emitting device (ED) can be further improved.

[0263] Each constituent layer of the hole transport region 120 can be formed by processes such as vacuum deposition, spin coating, inkjet printing, laser printing, casting and / or laser thermal transfer.

[0264] The electron transport region 140 can be formed between the second electrode 150 and the emitter layer 130. The electron transport region 140 can have a single-layer structure or a multi-layer structure comprising different materials.

[0265] The electron transport region 140 may include an electron injection layer, an electron transport layer and / or a hole blocking layer, and may also include an auxiliary emission layer.

[0266] In one or more embodiments, as shown in FIG2, the electron transport region 140 may include an electron injection layer 142 and an electron transport layer 144 stacked from the second electrode 150 to the emitter layer 130.

[0267] In one or more embodiments, as shown in FIG3, the electron transport region 140 may include an electron injection layer 142, an electron transport layer 144, and a hole blocking layer 146 stacked from the second electrode 150 to the emitter layer 130. The hole blocking layer 146 can block, suppress, or reduce the migration of holes from the hole transport region 120 to the electron transport region 140. Therefore, the emission energy and luminous efficiency in the emitter layer 130 can be further improved.

[0268] For example, in one or more embodiments, the electron transport region 140 may include the above-described compound represented by the chemical formula ET.

[0269] In one or more embodiments, the electron transport region 140 may include anthracene compounds, Alq3 (tris(8-hydroxyquinoline)aluminum), 1,3,5-tris[(3-pyridyl)-benzene-3-yl]benzene, 2,4,6-tris(3'-(pyridyl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, TPBi(1,3,5-tris[3'-(pyridyl)biphenyl-3-yl)-1,3,5-triazine] ...3'-(pyridyl)biphenyl-3-yl)-1,3,5-triazine], 2-(N-phenylbenzimidazol-1-yl)-phenyl)-9,10-dinaphthylanthracene, 2-(N-phenylbenzimidazol-1-yl)-phenyl)-9,10-dinaphthylanthracene, 2-(N-phenylbenzimidazol-1-yl)-phenyl)-9,10-dinaphthylanthracene, 2-(N-phenylbenzimidazol-1-yl)-phenyl)-1,3,5-triazine], 2-(N-phenylbenzimidazol-1-yl)-phenyl)-1,3,5-triazine], 2-(N-phenylben (1-Phenylacetyl-1H-benzo[d]imidazol-2-yl)benzene, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-diphenyl-1,10-phenanthroline), TAZ (3-(biphenyl-4-yl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole), NTAZ (4-(naphthyl-1-yl)-3,5-diphenyl-4H-1,2,4-triazole), t Bu-PBD (2-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole), BAlq (bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum), Bebq2 (bis(benzoquinoline-10-hydroxy)beryllium), ADN (9,10-bis(naphthyl-2-yl)anthracene), and / or BmPyPhB (1,3-bis[3,5-bis(pyridin-3-yl)phenyl]benzene), etc. The electron transport region 140 may include one of the above-described electron transport materials or a combination thereof (e.g., any suitable combination).

[0270] The aforementioned material may be included in at least one of the electron injection layer 142, the electron transport layer 144, and the hole blocking layer 146.

[0271] In one or more embodiments, the electron transport region 140 may include alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or combinations thereof (e.g., any suitable combination). In one or more embodiments, one or more of the above materials may be included in the electron injection layer 142.

[0272] Alkali metals may include Li, Na, K, Rb, Cs, or any combination thereof. Alkali earth metals may include Mg, Ca, Sr, Ba, or any combination thereof. Rare earth metals may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.

[0273] Alkali metal compounds, alkaline earth metal compounds, and rare earth metal compounds may respectively include oxides, halides (e.g., fluorides, chlorides, bromides, and / or iodides), tellurides, and / or combinations thereof (e.g., any suitable combination).

[0274] Alkali metal complexes, alkaline earth metal complexes, and rare earth metal complexes may include the corresponding metal ion (such as an alkali metal ion, alkaline earth metal ion, or rare earth metal ion) and a ligand bound to the corresponding metal ion. The ligand may include, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, and / or combinations thereof (e.g., any suitable combination).

[0275] The thickness of the electron transport region 140 can be in the range of about 100 Å to about 1,000 Å (e.g., about 150 Å to about 500 Å).

[0276] When the electron transport region 140 includes an electron injection layer 142 and / or an electron transport layer 144, the thickness of the electron injection layer 142 may be in the range of about 1 Å to about 100 Å, about 1 Å to about 90 Å, or about 5 Å to about 50 Å, and the thickness of the electron transport layer 144 may be in the range of about 10 Å to about 900 Å, about 10 Å to about 500 Å, or about 100 Å to about 400 Å.

[0277] Within any of the aforementioned thickness ranges, the electron injection and electron transport properties can be further improved without excessively increasing the driving voltage, and the stability of the electron transport region 140 can be improved.

[0278] Each constituent layer of the electron transport region 140 can be formed by processes such as vacuum deposition, spin coating, inkjet printing, laser printing, casting and / or laser thermal transfer.

[0279] In one or more embodiments, the light-emitting device (ED) may further include a capping layer. The capping layer can improve the luminous efficiency to the outside of the ED.

[0280] As shown in FIG4, the second capping layer 160b may be formed on the outer surface of the second electrode 150. In one or more embodiments, the first capping layer 160a may be formed on the outer surface of the first electrode 110.

[0281] The refractive index of the first capping layer 160a and / or the refractive index of the second capping layer 160b can both be 1.6 or greater. For example, in one or more embodiments, for light in the wavelength range of 550 nm to 660 nm, the refractive index of the first capping layer 160a and / or the refractive index of the second capping layer 160b can both be 1.6 or greater, 1.8 or greater, or 2.0 or greater.

[0282] The first capping layer 160a and the second capping layer 160b can both be formed as an organic capping layer including organic materials, an inorganic capping layer including inorganic materials, or an organic-inorganic mixed capping layer including both organic and inorganic materials (e.g., simultaneously).

[0283] The first cover layer 160a and / or the second cover layer 160b may each have a single-layer structure or a multi-layer structure comprising different materials.

[0284] In one or more embodiments, the first capping layer 160a and the second capping layer 160b may each independently comprise a carbocyclic compound, a heterocyclic compound, an amino-containing compound, a porphyrin derivative, a phthalocyanine derivative, a naphthalene phthalocyanine derivative, an alkali metal complex, and / or an alkaline earth metal complex, etc. The first capping layer 160a and the second capping layer 160b may each independently comprise one of the above materials or a combination thereof (e.g., any suitable combination).

[0285] In one or more embodiments, the first capping layer 160a and / or the second capping layer 160b may each independently comprise an amine-containing compound.

[0286] Referring to FIG5, in one or more embodiments, the light-emitting device ED may include multiple light-emitting structures (e.g., light-emitting structures ES1, ES2, and ES3). Light-emitting structures ES1, ES2, and ES3 may each include a stacked structure of a hole transport region 120, an emission layer 130, and an electron transport region 140 as described with reference to FIGS. 1 to 4. In one or more embodiments, the light-emitting device ED of FIG5 may be a light-emitting device with a series structure.

[0287] The charge generation layers CGL1 and CGL2 can be respectively arranged between adjacent structures in the light-emitting structures ES1, ES2 and ES3. The charge generation layers CGL1 and CGL2 can each independently include a p-type (p-class) charge (e.g., P charge) generation layer and / or an n-type (n-class) charge (e.g., N charge) generation layer.

[0288] The p-type (p-class) charge generation layer may include a hole transport host compound such as NPB. For example, in one or more embodiments, the p-type (p-class) charge generation layer may include a compound represented by the above chemical formula HT. In one or more embodiments, the p-type (p-class) charge generation layer may also include a p-doper such as TCNQ.

[0289] The n-type (n-class) charge generation layer may include an electron transport host compound. For example, in one or more embodiments, the n-type (n-class) charge generation layer may include a compound represented by the above chemical formula ET. In one or more embodiments, the n-type (n-class) charge generation layer may include a phenanthroline compound.

[0290] The charge generation layers CGL1 and CGL2 may include a first charge generation layer CGL1 disposed between the first light-emitting structure ES1 and the second light-emitting structure ES2, and a second charge generation layer CGL2 disposed between the second light-emitting structure ES2 and the third light-emitting structure ES3.

[0291] In one or more embodiments, the first light-emitting structure ES1, the first charge-generating layer CGL1, the second light-emitting structure ES2, the second charge-generating layer CGL2, the third light-emitting structure ES3, and the second electrode 150 may be sequentially stacked on the top surface of the first electrode 110.

[0292] The colors emitted from the first light-emitting structure ES1, the second light-emitting structure ES2, and the third light-emitting structure ES3 may be the same or different from each other. In one or more embodiments, the first light-emitting structure ES1, the second light-emitting structure ES2, and the third light-emitting structure ES3 may respectively include a red emission layer, a green emission layer, and a blue emission layer, and a white light-emitting structure can be achieved through a series structure, but the embodiments disclosed herein are not limited thereto.

[0293] Figure 5 illustrates a 3-stacked series structure in which three light-emitting structures are stacked, but the series structure of the light-emitting device (ED) of this disclosure is not limited to the structure shown in Figure 5. For example, 2-stacked, 4-stacked, 5-stacked, or 6-stacked structures or more, as described with reference to Figure 6, can also be implemented.

[0294] Referring to FIG6, as described with reference to FIG5, a series structure in which the light-emitting structure and the charge-generating layer are alternately and repeatedly stacked can be arranged between the first electrode 110 and the second electrode 150.

[0295] In one or more embodiments, the first light-emitting structures ES1 to the m-th light-emitting structures ESm can be sequentially stacked from the top surface of the first electrode 110 with a charge-generating layer disposed therebetween. The charge-generating layer may include the first charge-generating layer CGL1 to the (m-1)-th charge-generating layer CGLm-1 sequentially stacked from the top surface of the first electrode 110.

[0296] As shown in Figure 6, the first light-emitting structure ES1, the first charge-generating layer CGL1, the second light-emitting structure ES2, the second charge-generating layer CGL2, ..., the (m-1)th light-emitting structure ESm-1, the (m-1)th charge-generating layer CGLm-1, the mth light-emitting structure ESm, and the second electrode 150 can be sequentially stacked from the top surface of the first electrode 110.

[0297] In one or more embodiments, m is 4, and the intermediate layer ITL of the light-emitting device ED may have a 4-stacked series structure, and may include first to fourth light-emitting structures ES1, ES2, ES3 and ES4 and first to third charge-generating layers CGL1, CGL2 and CGL3. The colors of the light generated from the first to fourth light-emitting structures ES1, ES2, ES3 and ES4 may be the same or different from each other.

[0298] In one or more embodiments, the first to fourth light-emitting structures ES1, ES2, ES3 and ES4 may include at least one blue light-emitting structure and at least one green light-emitting structure. In a non-limiting example, the first to third light-emitting structures ES1, ES2 and ES3 may correspond to a blue light-emitting structure, and the fourth light-emitting structure ES4 may correspond to a green light-emitting structure.

[0299] In one or more embodiments, m is 5, and the intermediate layer ITL of the light-emitting device ED may have a 5-layer stacked series structure, and may include first to fifth light-emitting structures ES1, ES2, ES3, ES4 and ES5, and first to fourth charge-generating layers CGL1, CGL2, CGL3 and CGL4. The colors of the light generated by the first to fifth light-emitting structures ES1, ES2, ES3, ES4 and ES5 may be the same or different from each other.

[0300] In one or more embodiments, the first to fifth light-emitting structures ES1, ES2, ES3, ES4, and ES5 may include at least one blue light-emitting structure and at least one green light-emitting structure. In a non-limiting example, the first to fifth light-emitting structures ES1, ES2, ES3, ES4, and ES5 may include three blue light-emitting structures and two green light-emitting structures. For example, in one or more embodiments, the first light-emitting structure ES1, the third light-emitting structure ES3, and the fifth light-emitting structure ES5 may correspond to blue light-emitting structures, and the second light-emitting structure ES2 and the fourth light-emitting structure ES4 may correspond to green light-emitting structures.

[0301] The aforementioned light-emitting device (ED) can be applied to electronic devices and can be set as the light-emitting part or light-emitting unit of electronic devices.

[0302] Examples of electronic devices may include display devices, billboards, signs, light sources, lighting devices, personal computers such as laptop or desktop computers, mobile phones, e-books, electronic dictionaries, electronic notebooks, healthcare devices including diagnostic devices and one or more suitable sensors, and one or more suitable display units for transportation equipment (cars, airplanes, ships and / or trains, etc.).

[0303] In one or more embodiments, the light-emitting device ED can be applied to an organic light-emitting diode (OLED) display device or a quantum dot (QD)-OLED display device.

[0304] Figure 7 is a schematic cross-sectional view illustrating a display device according to one or more embodiments of the present disclosure.

[0305] Referring to FIG7, the display device may include a circuit layer CL disposed on a substrate 200 and light-emitting devices ED1, ED2 and ED3 disposed on the circuit layer CL.

[0306] The substrate 200 can be used as a support substrate or as a backplate substrate for a display device. The substrate 200 can be a glass substrate or a plastic substrate.

[0307] In one or more embodiments, the substrate 200 may include a polymeric material having transparent and flexible properties. If (for example, when) the substrate 200 includes a polymeric material, then the substrate 200 can be used in a transparent flexible display device. For example, in one or more embodiments, the substrate 200 may include polymeric materials such as polyimide, polysiloxane, epoxy resin, acrylic resin, and / or polyester. In one or more embodiments, the substrate 200 may include polyimide.

[0308] In one or more embodiments, the circuit layer CL may include transistors TR1, TR2, and TR3. The circuit layer CL may include wiring layers and insulating layers forming a thin-film transistor array (TFT array).

[0309] In one or more embodiments, the circuit layer CL may further include a buffer layer 205 on the top surface of the substrate 200. The buffer layer 205 may prevent moisture from penetrating through the substrate 200 and may also prevent the diffusion of impurities between the substrate 200 and the structures formed on the substrate 200.

[0310] Buffer layer 205 may include, for example, silicon oxide, silicon nitride, and / or silicon oxynitride. Buffer layer 205 may include one of the foregoing materials or a combination thereof (e.g., any suitable combination). In one or more embodiments, buffer layer 205 may have a stacked structure including a silicon oxide layer and a silicon nitride layer.

[0311] Transistors TR1, TR2, and TR3 can be arranged on buffer layer 205. The first transistor TR1, the second transistor TR2, and the third transistor TR3 can be electrically connected to the first light-emitting device ED1, the second light-emitting device ED2, and the third light-emitting device ED3, respectively.

[0312] Transistors TR1, TR2 and TR3 may each include an active layer 210, a gate insulating layer 220 and a gate electrode 230.

[0313] The active layer 210 may be disposed on the buffer layer 205 and may be patterned for each pixel. In one or more embodiments, the active layer 210 may comprise a silicon compound such as amorphous silicon or polycrystalline silicon. P-type (p-class) dopant or n-type (n-class) dopant may be doped in regions of the active layer 210, and the active layer 210 may comprise source regions, drain regions, and channel regions.

[0314] In one or more embodiments, the active layer 210 may include an oxide semiconductor such as indium gallium zinc oxide (IGZO), zinc tin oxide (ZTO), or ITZO.

[0315] A gate insulating layer 220 may be formed on the active layer 210, and a gate electrode 230 may be stacked on the gate insulating layer 220. As shown in FIG. 7, the gate insulating layer 220 may be patterned to partially cover each active layer 210. In one or more embodiments, the gate insulating layer 220 may extend continuously across multiple pixels or light-emitting regions and may be configured as a common layer for the first transistor TR1, the second transistor TR2, and the third transistor TR3.

[0316] The gate electrode 230 can be stacked with the channel region of the active layer 210 in the thickness direction.

[0317] An insulating intermediate layer 240 may be formed on the active layer 210 to cover the gate electrode 230 and the gate insulating layer 220. Connection electrodes 250 and 260, which may be in contact with or electrically connected to the active layer 210, may both be arranged on the insulating intermediate layer 240.

[0318] The connecting electrodes 250 and 260 may extend through the insulating intermediate layer 240 to contact or be electrically connected to the active layer 210. When the gate insulating layer 220 is configured as a common layer for multiple light-emitting regions, the connecting electrodes 250 and 260 may also extend through the gate insulating layer 220.

[0319] The connecting electrodes 250 and 260 may include a source electrode 250 and a drain electrode 260. The source electrode 250 may contact or be connected to the source region of the active layer 210, and the drain electrode 260 may contact or be connected to the drain region of the active layer 210.

[0320] The gate insulating layer 220 and the insulating intermediate layer 240 may each independently comprise silicon oxide, silicon nitride and / or silicon oxynitride, and may each have a stacked structure comprising a silicon oxide layer and a silicon nitride layer.

[0321] The gate electrode 230 and the connecting electrodes 250 and 260 may each independently comprise metals such as Ag, Mg, Al, W, Cu, Ni, Cr, Mo, Ti, Pt, Ta, Nd, Sc, their alloys, or their nitrides.

[0322] The via insulating layer 270 can be formed on the insulating intermediate layer 240 to cover the connecting electrodes 250 and 260.

[0323] The via insulating layer 270 can accommodate a via structure electrically connecting the first electrode 110 and the drain electrode 260. The via insulating layer 270 can serve as a planarization layer for the circuit layer CL. In one or more embodiments, the via insulating layer 270 may comprise organic materials such as polyimide, epoxy resin, acrylic resin, and / or polyester.

[0324] Light-emitting devices ED1, ED2, and ED3 can be disposed on via insulating layer 270. For example, as described with reference to Figures 1 to 4, light-emitting devices ED1, ED2, and ED3 can each include a first electrode 110, a hole transport region 120, an emission layer 130, an electron transport region 140, and a second electrode 150 sequentially stacked from via insulating layer 270.

[0325] The first electrode 110 can be electrically connected via a via structure to corresponding transistors TR1, TR2, and TR3 in the circuit layer CL, or to corresponding connection electrodes 250 and 260. As shown in FIG7, in one or more embodiments, the first electrode 110 can contact or be connected to the drain electrode 260 to serve as a pixel electrode for each light-emitting area or pixel patterning.

[0326] A pixel defining layer 280 can be formed on the via insulating layer 270 to define each light-emitting area or pixel. The blue light-emitting area, the red light-emitting area, and the green light-emitting area can be separated and defined by the pixel defining layer 280, and the light-emitting devices ED1, ED2, and ED3 can correspond to the blue light-emitting device, the red light-emitting device, and the green light-emitting device, respectively.

[0327] The pixel-defining layer 280 can partially cover the first electrode 110 of each light-emitting area.

[0328] As shown in Figure 7, the hole transport region 120 and the electron transport region 140 can both be configured as a common layer extending continuously over the pixel defining layer 280 and the first electrode 110. The emitting layer 130 can be formed within each light-emitting region or pixel and can be separated from the pixel defining layer 280.

[0329] In one or more embodiments, the emitting layer 130 may also be configured as a common layer extending continuously over the light-emitting region or pixels. In one or more embodiments, the hole transport region 120, the emitting layer 130, and the electron transport region 140 may all be patterned and formed individually for each light-emitting region or pixel.

[0330] The second electrode 150 can be configured as a common electrode that extends throughout the light-emitting area or continuously across the pixel.

[0331] The encapsulation layer 290 can be disposed on the pixel defining layer 280 and the light-emitting devices ED1, ED2 and ED3 to protect the light-emitting devices ED1, ED2 and ED3 from moisture and / or oxygen. The encapsulation layer 290 can be a thin-film encapsulation (TFE) with a single-layer structure or a multi-layer structure.

[0332] Encapsulation layer 290 may include: an inorganic layer, including silicon nitride (SiN) x ), silicon dioxide (SiO) xIndium tin oxide, indium zinc oxide, or any combination thereof; an organic layer, including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resin (e.g., polymethyl methacrylate and / or polyacrylic acid, etc.), epoxy resin (e.g., aliphatic glycidyl ether (AGE)), or any combination thereof; or a combination of an inorganic layer and an organic layer (e.g., any suitable).

[0333] The display device may also include a functional layer 300 disposed on the encapsulation layer 290. The functional layer 300 may include a sensor layer such as a touch sensor layer, an optical layer such as a polarization layer, a color conversion layer, a color filter layer, a window film, or any combination thereof.

[0334] Figure 8 is a schematic cross-sectional view illustrating a display device according to one or more embodiments of the present disclosure. For the sake of brevity, detailed descriptions of elements and structures that are substantially the same as or similar to those described with reference to FIG7 are omitted or simplified herein.

[0335] Referring to Figure 8, each of the light-emitting devices ED1, ED2 and ED3 can have a series structure, for example, a 2-stacked series structure.

[0336] In one or more embodiments, the hole transport region 120 and the electron transport region 140 may be continuously and commonly formed and included in the intermediate layer of each light-emitting structure. Additionally, the charge generation layer CGL may continuously extend across multiple pixels and may be commonly included in the intermediate layer of each light-emitting structure.

[0337] The first light-emitting device ED1 may include a first lower emitting layer 130-1a disposed between the hole transport region 120 and the charge generation layer CGL, and a first upper emitting layer 130-1b disposed between the charge generation layer CGL and the electron transport region 140.

[0338] The second light-emitting device ED2 may include a second lower emitting layer 130-2a disposed between the hole transport region 120 and the charge generation layer CGL, and a second upper emitting layer 130-2b disposed between the charge generation layer CGL and the electron transport region 140.

[0339] The third light-emitting device ED3 may include a third lower emitting layer 130-3a disposed between the hole transport region 120 and the charge generation layer CGL, and a third upper emitting layer 130-3b disposed between the charge generation layer CGL and the electron transport region 140.

[0340] The lower and upper emitting layers included in each light-emitting structure (e.g., in each tandem light-emitting structure) can produce light of the same color. In one or more embodiments, each of the first lower emitting layer 130-1a and the first upper emitting layer 130-1b included in the first light-emitting device ED1 can correspond to a red emitting layer. Each of the second lower emitting layer 130-2a and the second upper emitting layer 130-2b included in the second light-emitting device ED2 can correspond to a green emitting layer. Each of the third lower emitting layer 130-3a and the third upper emitting layer 130-3b included in the third light-emitting device ED3 can correspond to a blue emitting layer.

[0341] Figure 9 is a schematic cross-sectional view illustrating the stacked configuration of the light-emitting structure in a display device according to one or more embodiments of the present disclosure. For ease of illustration and description, descriptions of circuit layers, substrates, and / or pixel defining layers, etc., are omitted from Figure 9, and the shape of each layer or element in the light-emitting structure is simply shown as a rectangle.

[0342] Referring to FIG9, in one or more embodiments, at least one selected from the light-emitting devices ED1, ED2 and ED3 or the pixel regions PA1, PA2 and PA3 may have a series structure including multiple emission layers, and at least one selected from the remaining portions may have a single emission layer structure.

[0343] In one or more embodiments, the light-emitting devices ED1, ED2 and ED3 or the pixel regions PA1, PA2 and PA3 may have a series structure, and the remaining portion may have a single-emitting-layer structure.

[0344] As shown in Figure 9, the first light-emitting device ED1, the second light-emitting device ED2, and the third light-emitting device ED3 can be respectively included in the first pixel region PA1, the second pixel region PA2, and the third pixel region PA3. In one or more embodiments, the first pixel region PA1, the second pixel region PA2, and the third pixel region PA3 can correspond to the red pixel region, the green pixel region, and the blue pixel region, respectively.

[0345] Hole transport region 120, electron transport region 140 and second electrode 150 can all be configured as a common layer that extends continuously over the first pixel region PA1, the second pixel region PA2 and the third pixel region PA3.

[0346] The first light-emitting device ED1 included in the first pixel region PA1 may include a first emitting layer 130-1, and the second light-emitting device ED2 included in the second pixel region PA2 may include a second emitting layer 130-2. Each of the first emitting layer 130-1 and the second emitting layer 130-2 may be a single emitting layer.

[0347] The third light-emitting device ED3, included in the third pixel region PA3, may have, for example, a 2-stacked series structure. The third light-emitting device ED3 may include a third lower emitting layer 130-3a and a third upper emitting layer 130-3b separated by a charge generation layer CGL disposed therebetween. For example, each of the third lower emitting layer 130-3a and the third upper emitting layer 130-3b may correspond to a blue emitting layer.

[0348] The lower electron transport region 140a can be arranged between the charge generation layer CGL and the third lower emitter layer 130-3a. The upper hole transport region 120b can be arranged between the charge generation layer CGL and the third upper emitter layer 130-3b.

[0349] Therefore, a series light-emitting structure in which the first electrode 110, hole transport region 120, third lower emission layer 130-3a, lower electron transport region 140a, charge generation layer CGL, upper hole transport region 120b, third upper emission layer 130-3b, electron transport region 140, and second electrode 150 are stacked sequentially can be arranged in the third pixel region PA3.

[0350] Figure 10 is a schematic cross-sectional view illustrating a display device according to one or more embodiments of the present disclosure.

[0351] Figure 10 illustrates a display device having a QD-OLED structure according to one or more embodiments. For the sake of brevity, detailed descriptions of elements and structures that are the same as or substantially similar to those described with reference to FIG7 will not be repeated here.

[0352] Referring to FIG10, as described above with reference to FIG7, the pixel defining layer 280 and the light-emitting device ED can be arranged on the circuit layer CL. In one or more embodiments, each pixel can emit light in the same wavelength region. In one or more embodiments, each light-emitting device ED can emit blue light.

[0353] In one or more embodiments, as described above with respect to FIG. 5, each light-emitting region may include a light-emitting device having a series structure. In these embodiments, the intermediate layer ITL of each light-emitting device ED may be configured as a common layer extending continuously over multiple light-emitting regions.

[0354] The color control layer CCL can be disposed on the encapsulation layer 290, and the color control layer CCL can include color control units CCP1, CCP2 and CCP3.

[0355] Color control units CCP1, CCP2, and CCP3 may each include a light converter such as a quantum dot and / or a phosphor. In each of the color control units CCP1, CCP2, and CCP3, the light converter can convert the wavelength of the supplied light and emit the resulting light.

[0356] Color control units CCP1, CCP2, and CCP3 may be separated from each other or spaced apart and / or isolated (e.g., separated) by a dam BM. The dam BM may be substantially superimposed on the pixel defining layer 280, and color control units CCP1, CCP2, and CCP3 may be substantially superimposed on each of the emission layers 130.

[0357] The color control layer (CCL) may include a first color control unit (CCP1), a second color control unit (CCP2), and a third color control unit (CCP3). The first color control unit (CCP1) includes a first quantum dot that converts first color light provided by the light-emitting device (ED) into second color light. The second color control unit (CCP2) includes a second quantum dot that converts first color light into third color light. The third color control unit (CCP3) transmits first color light.

[0358] In one or more embodiments, the first color light, the second color light, and the third color light can be blue light, red light, and green light, respectively. The first quantum dot and the second quantum dot can be red quantum dot and green quantum dot, respectively.

[0359] Color control units CCP1, CCP2, and CCP3 may each further include a scattering material such as inorganic particles. The third color control unit CCP3 may not include quantum dots (e.g., any one of the quantum dots may be excluded) and may include a scattering material. The scattering material may include TiO2, ZnO, Al2O3, SiO2, and / or hollow silica, etc. The scattering material may be one of the aforementioned materials or a combination thereof (e.g., any suitable combination).

[0360] Color control units CCP1, CCP2, and CCP3 may each further include a binder resin for dispersing quantum dots and scattering materials. The binder resin may include acrylic resin, urethane resin, silicone resin, and / or epoxy resin, etc.

[0361] The color filter layer CFL, which includes filters CF1 and CF2 and the light-shielding part CP, can be arranged on the color control layer CCL.

[0362] The color filter layer (CFL) may include a first filter CF1 that transmits a second color of light, a second filter CF2 that transmits a third color of light, and a third filter that transmits a first color of light. For example, the first filter CF1 may be a red filter, the second filter CF2 may be a green filter, and the third filter may be a blue filter.

[0363] Filters CF1 and CF2 may both include a photosensitive adhesive resin and a colorant including pigments and / or dyes. The first filter CF1 may include red pigments and / or red dyes, and the second filter CF2 may include green pigments and / or green dyes.

[0364] The light-shielding portion CP can be arranged between the filters. In one or more embodiments, the light-shielding portion CP may include a first light-shielding portion CP1 and a second light-shielding portion CP2 containing colorants of different colors.

[0365] In one or more embodiments, the first light-shielding portion CP1 may include a blue colorant, and the second light-shielding portion CP2 may include a red colorant or a black colorant. In one or more embodiments, in the blue emitting region, a portion of the first light-shielding portion CP1 may be configured as a blue filter and may be exposed between the second light-shielding portions CP2, such that no additional filter (e.g., a third filter) is required.

[0366] The first barrier layer 310 can be disposed between the color control layer CCL and the light-emitting device ED (or the encapsulation layer 290). The second barrier layer 320 can be disposed between the color control layer CCL and the color filter layer CFL.

[0367] Both barrier layers 310 and 320 may include at least one inorganic layer. For example, both barrier layers 310 and 320 may independently include silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, and / or silicon oxynitride.

[0368] In one or more embodiments, both barrier layers 310 and 320 may have a multilayer structure that also includes an organic layer.

[0369] Figure 11 is a schematic cross-sectional view illustrating a display device according to one or more embodiments of the present disclosure. Detailed descriptions of elements and structures that are substantially the same as or similar to those described with reference to FIG10 are omitted herein.

[0370] Referring to FIG11, the light-emitting devices ED corresponding to the color control units CCP1, CCP2 and CCP3 can be arranged on the first electrode 110 used as pixel electrode, and the light-emitting devices ED can have a series structure.

[0371] In one or more embodiments, as described with reference to FIG5, the first light-emitting structure ES1, the first charge-generating layer CGL1, the second light-emitting structure ES2, the second charge-generating layer CGL2, and the third light-emitting structure ES3 may be sequentially stacked between the first electrode 110 and the second electrode 150. In one or more embodiments, the first light-emitting structure ES1, the first charge-generating layer CGL1, the second light-emitting structure ES2, the second charge-generating layer CGL2, and the third light-emitting structure ES3 may be continuously and commonly formed in multiple pixel regions or light-emitting regions.

[0372] In one or more embodiments, the first light-emitting structure ES1, the second light-emitting structure ES2, and the third light-emitting structure ES3 can produce light of different colors, and the light-emitting device ED can produce white light (e.g., combined white light). In one or more embodiments, the first light-emitting structure ES1, the second light-emitting structure ES2, and the third light-emitting structure ES3 can all produce blue light.

[0373] In one or more embodiments, as described with reference to FIG6, the light-emitting device ED may include a series structure of 4 stacks, 5 stacks or more stacks.

[0374] Figure 12 is a block diagram of an electronic device according to one or more embodiments of the present disclosure.

[0375] Referring to FIG12, an electronic device 10 according to one or more embodiments may include a display module 11, a processor 12, a memory 13, and a power module 14.

[0376] The processor 12 may include a central processing unit (CPU), an application processor (AP), a graphics processing unit (GPU), a communication processor (CP), an image signal processor (ISP), and / or a controller.

[0377] Data information for the operation of processor 12 and / or display module 11 can be stored in memory 13. When processor 12 executes the application stored in memory 13, image data signals and / or input control signals can be sent to display module 11, and display module 11 can process the received signals and output image information through the display screen.

[0378] The power module 14 may include a power module such as a power adapter and / or battery device, and a power conversion module that converts the power supplied by the power module to generate the power desired or required for the operation of the electronic device 10.

[0379] At least one of the components selected from the electronic device 10 described above may be included in the display device according to the above embodiments. Additionally, some modules that are functionally included in a single module may be included in the display device, while other modules may be disposed separately from the display device. For example, display module 11 may be included in the display device, and processor 12, memory 13, and power module 14 may be disposed in the electronic device 10 as a separate device from the display device.

[0380] Figure 13 is a schematic diagram illustrating an electronic device according to various embodiments of the present disclosure.

[0381] Referring to FIG13, non-limiting examples of one or more suitable electronic devices applied to the display device according to the above embodiments may include: electronic devices for displaying images, such as smartphones 10_1a, tablet PCs 10_1b, laptop computers 10_1c, TVs 10_1d, and / or desktop monitors 10_1e; wearable electronic devices including display modules, such as smart glasses 10_2a, head-mounted displays 10_2b, and / or smartwatches 10_2c; and vehicle electronic devices 10_3 including display modules, such as central information displays (CIDs) and / or interior mirror displays arranged in vehicle dashboards, center dashboards, and / or instrument panels. The electronic devices may include virtual reality glasses or augmented reality glasses.

[0382] Figure 14 is a schematic exploded perspective view illustrating an electronic device according to one or more embodiments of the present disclosure.

[0383] According to one or more embodiments, the electronic device can be implemented in the form of a mobile phone (smartphone), tablet computer, and / or PC, etc., including the display device described above.

[0384] Referring to FIG14, the electronic device may include a window structure WS, a display panel DP, and a rear structure RS.

[0385] The window structure WS can provide an external display surface that can be recognized by the user (such as the viewing surface of a mobile phone) and can include a transparent material film. For example, the window structure WS can include glass (e.g., ultra-thin glass (UTG)), hard-coated films, and / or plastic films, etc.

[0386] The outer surface of the window structure WS may include an effective area AA and a peripheral area PA. The effective area AA provides a surface from which the image of the display device is substantially displayed, and from which user touch / command input is made. The peripheral area PA may substantially correspond to the bezel area of ​​the display device.

[0387] The display panel DP may include the aforementioned display device and may have a display area DA and a non-display area NDA. The display area DA of the display panel DP may substantially correspond to the effective area AA of the window structure WS or be superimposed on the effective area AA of the window structure WS. The non-display area NDA of the display panel DP may substantially correspond to the peripheral area PA of the window structure WS or be superimposed on the peripheral area PA of the window structure WS.

[0388] In one or more embodiments, functional device regions E1 and E2 may be included in the effective area AA of the window structure WS. For example, the first functional device region E1 may be included at one end of the effective area AA and may be implemented, for example, in the form of a camera hole. The second functional device region E2 may be used as a fingerprint sensing area.

[0389] For example, in one or more embodiments, the sensor structure for touch sensing or fingerprint sensing may be arranged in the display panel DP or between the window structure WS and the display panel DP.

[0390] The rear structure RS can be used as a frame structure or housing for a display device or electronic device. A cover panel can be arranged between the rear structure RS and the display panel DP.

[0391] Figure 15 is a schematic cross-sectional view illustrating an electronic device according to one or more embodiments of the present disclosure.

[0392] Electronic devices may be installed in, embedded in, attached to, or integrated with vehicle 400. However, vehicle 400 is not limited to one or more embodiments shown in FIG. 15. Other examples of vehicle 400 may include transportation equipment such as three-wheeled or four-wheeled vehicles, construction machinery, two-wheeled vehicles, motor vehicles, bicycles, and / or trains. Other examples of vehicle 400 may also include electric vehicles and / or hybrid vehicles.

[0393] Referring to FIG15, at least one of the first to fifth display devices DP1, DP2, DP3, DP4 and DP5 can be applied to vehicle 400.

[0394] In one or more embodiments, the first display device DP1 may be arranged in cluster area 410. Driving information such as driving distance and speed, as well as one or more suitable warning lights, may be displayed in cluster area 410.

[0395] The second display device DP2 can be mounted on the windshield (FW) of the vehicle 400. For example, the second display device DP2 can be installed as a head-up display (HUD).

[0396] The third display device DP3 can be arranged on the central instrument panel 420 of the vehicle 400. The central instrument panel 420 can display buttons and / or switches for controlling the image display or music player, air conditioning and / or heater, etc., and can display vehicle information thereon.

[0397] The fourth display device DP4 can be applied to the side mirrors 430 of the vehicle 400. The side mirrors 430 can be installed on each of the two sides (e.g., two opposite sides) of the exterior of the vehicle 400, and the fourth display device DP4 can be applied to at least one of the side mirrors 430 installed on each of the two sides.

[0398] A fifth display device DP5 may be mounted on the passenger seat instrument panel 440. Information / images that are the same as or different from those displayed on the cluster area 410 and / or the central instrument panel 420 may be displayed on the passenger seat instrument panel 440.

[0399] The aforementioned light-emitting device (ED) can be applied to electronic devices and can be used as a light-emitting part or light-emitting unit of electronic devices.

[0400] In one or more embodiments, the electronic device may include the electronic device described above.

[0401] Electronic devices may include, for example, video walls, flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, indoor lights, outdoor lights, signal lights, head-up displays, fully transparent displays, partially transparent displays, flexible displays, rollable displays, foldable displays, laser printers, telephones, mobile phones, tablet computers, tablet phones, personal information terminals (PDAs), wearable devices, laptop computers, digital cameras, camcorders, viewfinders, microdisplays, 3D displays, virtual reality displays, augmented reality displays, vehicles, video walls including multiple displays spliced ​​together, theater screens, stadium screens, light therapy devices, and / or signs.

[0402] In the following description, condensed heterocyclic compounds according to one or more embodiments will be described in more detail with reference to examples and comparative examples. Examples are provided to aid in understanding the disclosure, but they are provided by way of non-limiting examples, and the scope of the disclosure is not limited thereto. It will be apparent to those skilled in the art that one or more suitable changes and modifications can be made to the disclosed examples within the scope of the disclosure.

[0403] Example 1: Synthesis of Compound 1

[0404] (1) Synthesis of Intermediate 1-1: N-(5-bromo-[1,1'-biphenyl]-3-yl)-[1,1':3',1''-terphenyl]-2'-amine (1 equivalent), 3-iodo-1,1'-biphenyl (2 equivalents), tris(dibenzylacetone)dipalladium (0) (0.15 equivalents), tri-tert-butylphosphine (0.3 equivalents), and sodium tert-butoxide (5 equivalents) were dissolved in o-xylene and stirred at 150 °C for 48 hours. After cooling, the mixture was washed with ethyl acetate and water. The organic layer was separated and dried with anhydrous MgSO4, followed by drying under reduced pressure. Intermediate 1-1 was obtained by column chromatography using dichloromethane (MC) and n-hexane as the developing solvent (yield: 49%).

[0405] (2) Synthesis of Intermediate 1-2: Intermediate 1-1 (1 equivalent), 4-chlorophenol (1.2 equivalent), CuI (0.1 equivalent), 2-pyridinecarboxylic acid (0.1 equivalent), and K2CO3 (3 equivalent) were dissolved in dimethylformamide (DMF) and stirred at 160 °C for 12 hours. After cooling, the solvent was removed under reduced pressure and the mixture was washed with ethyl acetate and water. The organic layer was separated and dried with anhydrous MgSO4, followed by drying under reduced pressure. Intermediate 1-2 (yield: 72%) was obtained by column chromatography using MC and n-hexane as the developing solvent.

[0406] (3) Synthesis of Intermediate 1-3: N-(5-bromo-[1,1'-biphenyl]-3-yl)-[1,1':3',1''-terphenyl]-2'-amine (1 equivalent), [1,1'-biphenyl]-3-ol (1.2 equivalent), CuI (0.1 equivalent), 2-pyridinecarboxylic acid (0.1 equivalent), and K2CO3 (3 equivalent) were dissolved in DMF and stirred at 160 °C for 12 hours. After cooling, the solvent was removed under reduced pressure and the mixture was washed with ethyl acetate and water. The organic layer was separated and dried with anhydrous MgSO4, followed by drying under reduced pressure. Intermediate 1-3 was purified by column chromatography using MC and n-hexane as the developing solvent to obtain intermediate 1-3 (yield: 69%).

[0407] (4) Synthesis of Intermediates 1-4: Intermediates 1-2 (1.3 equivalents), 1-3 (1 equivalent), tris(dibenzylacetone)dipalladium(0) (0.15 equivalents), tri-tert-butylphosphine (0.3 equivalents), and sodium tert-butoxide (5 equivalents) were dissolved in o-xylene and stirred at 150 °C for 48 hours. After cooling, the mixture was washed with ethyl acetate and water. The organic layer was separated and dried with anhydrous MgSO4, followed by vacuum drying. Intermediates 1-4 (yield: 43%) were purified by column chromatography using MC and n-hexane as the developing solvent.

[0408] (5) Synthesis of Compound 1: Intermediate 1-4 (1 equivalent) was dissolved in o-dichlorobenzene in a flask, cooled to 0°C, and BBr3 (3 equivalents) was slowly injected under a nitrogen atmosphere. The temperature was then raised to 180°C and stirred for 24 hours. After cooling the mixture, triethylamine was slowly added dropwise to the flask to terminate the reaction, followed by the addition of ethanol. The product was obtained by precipitation and filtration. The obtained solid was purified by column chromatography using MC and n-hexane as the developing solvent, and then compound 1 (yield: 19%) was obtained by recrystallization from toluene and acetone.

[0409] Example 2: Synthesis of Compound 2

[0410] (1) Synthesis of Intermediate 2-1: N-(5-bromo-[1,1'-biphenyl]-3-yl)-[1,1':3',1''-terphenyl]-2'-amine (1 equivalent), 4-iodo-1,1'-biphenyl (2 equivalents), tris(dibenzylacetone)dipalladium (0) (0.15 equivalents), tri-tert-butylphosphine (0.3 equivalents), and sodium tert-butoxide (5 equivalents) were dissolved in o-xylene and stirred at 150 °C for 48 hours. After cooling, the mixture was washed with ethyl acetate and water. The organic layer was separated and dried with anhydrous MgSO4, followed by drying under reduced pressure. Intermediate 2-1 (yield: 55%) was obtained by column chromatography using MC and n-hexane as the developing solvent.

[0411] (2) Synthesis of Intermediate 2-2: Intermediate 2-1 (1 equivalent), 4-chlorophenol (1.2 equivalent), CuI (0.1 equivalent), 2-pyridinecarboxylic acid (0.1 equivalent), and K2CO3 (3 equivalent) were dissolved in DMF and stirred at 160 °C for 12 hours. After cooling, the solvent was removed under reduced pressure and the mixture was washed with ethyl acetate and water. The organic layer was separated and dried with anhydrous MgSO4, followed by drying under reduced pressure. Intermediate 2-2 (yield: 74%) was obtained by column chromatography using MC and n-hexane as the developing solvent.

[0412] (3) Synthesis of Intermediate 2-3: N-(5-bromo-[1,1'-biphenyl]-3-yl)-[1,1':3',1''-terphenyl]-2'-amine (1 equivalent), [1,1'-biphenyl]-4-ol (1.2 equivalent), CuI (0.1 equivalent), 2-pyridinecarboxylic acid (0.1 equivalent), and K2CO3 (3 equivalent) were dissolved in DMF and stirred at 160 °C for 12 hours. After cooling, the solvent was removed under reduced pressure and the mixture was washed with ethyl acetate and water. The organic layer was separated and dried with anhydrous MgSO4, followed by drying under reduced pressure. Intermediate 2-3 (yield: 70%) was obtained by column chromatography using MC and n-hexane as the developing solvent.

[0413] (4) Synthesis of Intermediate 2-4: Intermediate 2-2 (1.3 equivalents), intermediate 2-3 (1 equivalent), tris(dibenzylacetone)dipalladium(0) (0.15 equivalents), tri-tert-butylphosphine (0.3 equivalents), and sodium tert-butoxide (5 equivalents) were dissolved in o-xylene and stirred at 150 °C for 48 hours. After cooling, the mixture was washed with ethyl acetate and water. The organic layer was separated and dried with anhydrous MgSO4, followed by drying under reduced pressure. Intermediate 2-4 (yield: 47%) was obtained by column chromatography using MC and n-hexane as the developing solvent.

[0414] (5) Synthesis of Compound 2: Intermediate 2-4 (1 equivalent) was dissolved in o-dichlorobenzene in a flask, cooled to 0°C, and BBr3 (3 equivalents) was slowly injected under a nitrogen atmosphere. The temperature was then raised to 180°C and stirred for 24 hours. After cooling the mixture, triethylamine was slowly added dropwise to the flask to terminate the reaction, and then ethanol was added to the flask to obtain the product by precipitation and filtration. The obtained solid was purified by column chromatography using MC and n-hexane as the developing solvent, and then compound 2 (yield: 14%) was obtained by recrystallization from toluene and acetone.

[0415] Example 3: Synthesis of Compound 3

[0416] (1) Synthesis of Intermediate 3-1: Intermediate 1-2 (1.3 equivalents) of Example 1, intermediate 2-3 (1 equivalent) of Example 2, tris(dibenzylacetone)dipalladium(0) (0.15 equivalents), tri-tert-butylphosphine (0.3 equivalents), and sodium tert-butoxide (5 equivalents) were dissolved in o-xylene and stirred at 150 °C for 48 hours. After cooling, the mixture was washed with ethyl acetate and water. The organic layer was separated and dried with anhydrous MgSO4, followed by drying under reduced pressure. Intermediate 3-1 (yield: 52%) was obtained by column chromatography using MC and n-hexane as the developing solvent.

[0417] (2) Synthesis of Compound 3: Intermediate 3-1 (1 equivalent) was dissolved in o-dichlorobenzene in a flask, cooled to 0°C, and BBr3 (3 equivalents) was slowly injected under a nitrogen atmosphere. The temperature was then raised to 180°C and stirred for 24 hours. After cooling, triethylamine was slowly added dropwise to the flask to terminate the reaction, and then ethanol was added to the flask to obtain the product by precipitation and filtration. The obtained solid was purified by column chromatography using MC and n-hexane as the developing solvent, and then compound 3 (yield: 21%) was obtained by recrystallization from toluene and acetone.

[0418] Example 4: Synthesis of Compound 13

[0419] (1) Synthesis of Intermediate 13-1: N-(5-bromo-[1,1'-biphenyl]-3-yl)-[1,1':3',1''-terphenyl]-2'-amine (1 equivalent), 9-(3-iodophenyl)-9H-carbazole (2 equivalents), tris(dibenzylacetone)dipalladium(0) (0.15 equivalents), tri-tert-butylphosphine (0.3 equivalents), and sodium tert-butoxide (5 equivalents) were dissolved in o-xylene and stirred at 150 °C for 48 hours. After cooling, the mixture was washed with ethyl acetate and water. The organic layer was separated and dried with anhydrous MgSO4, followed by drying under reduced pressure. Intermediate 13-1 (yield: 43%) was obtained by column chromatography using MC and n-hexane as the developing solvent.

[0420] (2) Synthesis of Intermediate 13-2: Intermediate 13-1 (1 equivalent), 4-chlorophenol (1.2 equivalent), CuI (0.1 equivalent), 2-pyridinecarboxylic acid (0.1 equivalent), and K2CO3 (3 equivalent) were dissolved in DMF and stirred at 160 °C for 12 hours. After cooling the mixture, the solvent was removed under reduced pressure and the mixture was washed with ethyl acetate and water. The organic layer was separated and dried with anhydrous MgSO4, followed by drying under reduced pressure. Intermediate 13-2 (yield: 77%) was obtained by column chromatography using MC and n-hexane as the developing solvent.

[0421] (3) Synthesis of Intermediate 13-3: N-(5-bromo-[1,1'-biphenyl]-3-yl)-[1,1':3',1''-terphenyl]-2'-amine (1 equivalent), 3-(9H-carbazole-9-yl)phenol (1.2 equivalent), CuI (0.1 equivalent), 2-pyridinecarboxylic acid (0.1 equivalent), and K2CO3 (3 equivalent) were dissolved in DMF and stirred at 160 °C for 12 hours. After cooling the mixture, the solvent was removed under reduced pressure and the mixture was washed with ethyl acetate and water. The organic layer was separated and dried with anhydrous MgSO4, followed by drying under reduced pressure. Intermediate 13-3 (yield: 70%) was obtained by column chromatography using MC and n-hexane as the developing solvent.

[0422] (4) Synthesis of Intermediate 13-4: Intermediate 13-2 (1.3 equivalents), intermediate 13-3 (1 equivalent), tris(dibenzylacetone)dipalladium(0) (0.15 equivalents), tri-tert-butylphosphine (0.3 equivalents), and sodium tert-butoxide (5 equivalents) were dissolved in o-xylene and stirred at 150 °C for 48 hours. After cooling, the mixture was washed with ethyl acetate and water. The organic layer was separated and dried with anhydrous MgSO4, followed by drying under reduced pressure. Intermediate 13-4 (yield: 50%) was obtained by column chromatography using MC and n-hexane as the developing solvent.

[0423] (5) Synthesis of Compound 13: Intermediate 13-4 (1 equivalent) was dissolved in o-dichlorobenzene in a flask and cooled to 0°C. BBr3 (3 equivalents) was then slowly added under a nitrogen atmosphere. The temperature was then raised to 180°C and stirred for 24 hours. After cooling the mixture, triethylamine was slowly added dropwise to the flask to terminate the reaction. Ethanol was then added to the flask to obtain the product by precipitation and filtration. The obtained solid was purified by column chromatography using MC and n-hexane as the developing solvent, and then recrystallized using toluene and acetone to obtain compound 13 (yield: 18%).

[0424] Example 5: Synthesis of Compound 85

[0425] (1) Synthesis of Intermediate 85-1: N-(3-bromo-5-(tert-butyl)phenyl)-[1,1':3',1''-terphenyl]-2'-amine (1 equivalent), 3-iodo-1,1'-biphenyl (2 equivalents), tris(dibenzylacetone)dipalladium(0) (0.15 equivalents), tri-tert-butylphosphine (0.3 equivalents), and sodium tert-butoxide (5 equivalents) were dissolved in o-xylene and stirred at 150 °C for 48 hours. After cooling, the mixture was washed with ethyl acetate and water. The organic layer was separated and dried with anhydrous MgSO4, followed by vacuum drying. Intermediate 85-1 was obtained by column chromatography using MC and n-hexane as the developing solvent (yield: 54%).

[0426] (2) Synthesis of Intermediate 85-2: Intermediate 85-1 (1 equivalent), 4-chlorophenol (1.2 equivalent), CuI (0.1 equivalent), 2-pyridinecarboxylic acid (0.1 equivalent), and K2CO3 (3 equivalent) were dissolved in DMF and stirred at 160 °C for 12 hours. After cooling the mixture, the solvent was removed under reduced pressure and the mixture was washed with ethyl acetate and water. The organic layer was separated and dried with anhydrous MgSO4, followed by drying under reduced pressure. Intermediate 85-2 (yield: 77%) was obtained by column chromatography using MC and n-hexane as the developing solvent.

[0427] (3) Synthesis of Intermediate 85-3: N-(3-bromo-5-(tert-butyl)phenyl)-[1,1':3',1''-terphenyl]-2'-amine (1 equivalent), [1,1'-biphenyl]-3-ol (1.2 equivalent), CuI (0.1 equivalent), 2-pyridinecarboxylic acid (0.1 equivalent), and K2CO3 (3 equivalent) were dissolved in DMF and stirred at 160 °C for 12 hours. After cooling the mixture, the solvent was removed under reduced pressure and the mixture was washed with ethyl acetate and water. The organic layer was separated and dried with anhydrous MgSO4, followed by drying under reduced pressure. Intermediate 85-3 (yield: 70%) was obtained by column chromatography using MC and n-hexane as the developing solvent.

[0428] (4) Synthesis of Intermediate 85-4: Intermediate 85-2 (1.3 equivalents), intermediate 85-3 (1 equivalent), tris(dibenzylacetone)dipalladium(0) (0.15 equivalents), tri-tert-butylphosphine (0.3 equivalents), and sodium tert-butoxide (5 equivalents) were dissolved in o-xylene and stirred at 150 °C for 48 hours. After cooling, the mixture was washed with ethyl acetate and water. The organic layer was separated and dried with anhydrous MgSO4, followed by vacuum drying. Intermediate 85-4 (yield: 42%) was obtained by column chromatography using MC and n-hexane as the developing solvent.

[0429] (5) Synthesis of Compound 85: Intermediate 85-4 (1 equivalent) was dissolved in o-dichlorobenzene in a flask and cooled to 0°C. BBr3 (3 equivalents) was then slowly added under a nitrogen atmosphere. The temperature was then raised to 180°C and stirred for 24 hours. After cooling the mixture, triethylamine was slowly added dropwise to the flask to terminate the reaction. Ethanol was then added to the flask to obtain the product by precipitation and filtration. The obtained solid was purified by column chromatography using MC and n-hexane as the developing solvent, and then recrystallized from toluene and acetone to obtain compound 85 (yield: 17%).

[0430] Example 6: Synthesis of Compound 193

[0431] (1) Synthesis of Intermediate 193-1: N-(3-(tert-butyl)-5-((4-chlorophenyl)thio)phenyl)-N-(3-(tert-butyl)phenyl)-[1,1':3',1''-terphenyl]-2'-amine (1 equivalent), N-(3-(tert-butyl)-5-((3-(tert-butyl)phenyl)thio)phenyl)-[1,1':3',1''-terphenyl]-2'-amine (1 equivalent), tris(dibenzylideneacetone)dipalladium(0) (0.15 equivalent), tritert-butylphosphine (0.3 equivalent), and sodium tert-butoxide (5 equivalent) were dissolved in o-xylene and stirred at 150 °C for 48 hours. After cooling, the mixture was washed with ethyl acetate and water. The organic layer was separated and dried with anhydrous MgSO4, followed by vacuum drying. The mixture was purified by column chromatography using MC and n-hexane as the developing solvent to obtain intermediate 193-1 (yield: 48%).

[0432] (2) Synthesis of Compound 193: Intermediate 193-1 (1 equivalent) was dissolved in o-dichlorobenzene in a flask and cooled to 0°C. BBr3 (3 equivalents) was then slowly injected under a nitrogen atmosphere. The temperature was then raised to 180°C and stirred for 24 hours. After cooling the mixture, triethylamine was slowly added dropwise to the flask to terminate the reaction. Ethanol was then added to the flask to obtain the product by precipitation and filtration. The obtained solid was purified by column chromatography using MC and n-hexane as the developing solvent, and then compound 193 (yield: 14%) was obtained by recrystallization from toluene and acetone.

[0433] Example 7: Synthesis of compound 199

[0434] (1) Synthesis of intermediate 199-1: 5'-chloro-3'-fluoro-1,1':2',1''-terphenyl (1 eq), [1,1'-biphenyl]-3-ol (1.5 eq), and K3PO4 (2 eq) were dissolved in DMF and stirred at 160 °C for 12 hours. After cooling, the solvent was removed under reduced pressure and the mixture was washed with ethyl acetate and water. The organic layer was separated and dried over anhydrous MgSO4, followed by drying under reduced pressure. Intermediate 199-1 (yield: 81%) was obtained by column chromatography using MC and n-hexane as the developing solvent.

[0435] (2) Synthesis of Intermediate 199-2 Intermediate 199-1 (1 eq), [1,1':3',1''-terphenyl]-2'-amine (1.3 eq), tris(dibenzylacetone)dipalladium (0) (0.05 eq), tri-tert-butylphosphine (0.1 eq), and sodium tert-butoxide (3 eq) were dissolved in toluene and stirred at 100 °C for 12 hours. After cooling, the solvent was removed under reduced pressure and the mixture was washed with ethyl acetate and water. The organic layer was separated and dried over anhydrous MgSO4, followed by drying under reduced pressure. Intermediate 199-2 (yield: 83%) was obtained by column chromatography using MC and n-hexane as the developing solvent.

[0436] (3) Synthesis of Intermediate 199-3: Intermediate 199-2 (1 eq), intermediate 1-2 (1.4 eq), tris(dibenzylacetone)dipalladium (0) (0.15 eq), tri-tert-butylphosphine (0.3 eq), and sodium tert-butoxide (5 eq) were dissolved in o-xylene and stirred at 150 °C for 48 hours. After cooling, the solvent was removed under reduced pressure and the mixture was washed with ethyl acetate and water. The organic layer was separated and dried with anhydrous MgSO4, followed by drying under reduced pressure. Intermediate 199-3 (yield: 48%) was obtained by column chromatography using MC and n-hexane as the developing solvent.

[0437] (4) Synthesis of Compound 199: Intermediate 199-3 (1 equivalent) and 2,6-dichloropyridine (5 eq) were dissolved in o-dichlorobenzene in a flask, cooled to 0°C, and BBr3 (5 equivalent) was slowly injected under a nitrogen atmosphere. The temperature was then raised to 180°C and stirred for 24 hours. After cooling the mixture, triethylamine was slowly added dropwise to the flask to terminate the reaction, followed by the addition of ethanol to the flask to obtain the product by precipitation and filtration. The obtained solid was purified by column chromatography using MC and n-hexane as the developing solvent, and then compound 199 (yield: 17%) was obtained by recrystallization from toluene and acetone.

[0438] Example 8: Synthesis of Compound 201

[0439] (1) Synthesis of intermediate 201-1: 5'-bromo-3'-fluoro-1,1':2',1''-terphenyl (1 eq), 4-chlorophenol (1.5 eq), and K3PO4 (2 eq) were dissolved in DMF and stirred at 160 °C for 12 hours. After cooling, the solvent was removed under reduced pressure and the mixture was washed with ethyl acetate and water. The organic layer was separated and dried with anhydrous MgSO4, followed by drying under reduced pressure. Intermediate 201-1 (yield: 79%) was obtained by column chromatography using MC and n-hexane as the developing solvent.

[0440] (2) Synthesis of Intermediate 201-2 Intermediate 201-1 (1 eq), N-([1,1'-biphenyl]-3-yl)-[1,1':3',1''-terphenyl]-2'-amine (1.1 eq), tris(dibenzylacetone)dipalladium (0) (0.15 eq), tri-tert-butylphosphine (0.3 eq), and sodium tert-butoxide (5 eq) were dissolved in o-xylene and stirred at 150 °C for 24 hours. After cooling, the solvent was removed under reduced pressure and the mixture was washed with ethyl acetate and water. The organic layer was separated and dried over anhydrous MgSO4, followed by drying under reduced pressure. Intermediate 201-2 (yield: 32%) was obtained by column chromatography using MC and n-hexane as the developing solvent.

[0441] (3) Synthesis of Intermediate 201-3: Intermediate 201-2 (1 eq), intermediate 199-2 (1.3 eq), tris(dibenzylacetone)dipalladium (0) (0.15 eq), tri-tert-butylphosphine (0.3 eq), and sodium tert-butoxide (5 eq) were dissolved in o-xylene and stirred at 150 °C for 48 hours. After cooling, the solvent was removed under reduced pressure and the mixture was washed with ethyl acetate and water. The organic layer was separated and dried with anhydrous MgSO4, followed by drying under reduced pressure. Intermediate 201-3 (yield: 45%) was obtained by column chromatography using MC and n-hexane as the developing solvent.

[0442] (4) Synthesis of Compound 201: Intermediate 201-3 (1 equivalent) and 2,6-dichloropyridine (5 eq) were dissolved in o-dichlorobenzene in a flask, cooled to 0°C, and BBr3 (5 equivalent) was slowly injected under a nitrogen atmosphere. The temperature was then raised to 180°C and stirred for 24 hours. After cooling the mixture, triethylamine was slowly added dropwise to the flask to terminate the reaction, and then ethanol was added to the flask to obtain the product by precipitation and filtration. The obtained solid was purified by column chromatography using MC and n-hexane as the developing solvent, and then compound 201 (yield: 14%) was obtained by recrystallization from toluene and acetone.

[0443] Example 9: Synthesis of compound 222

[0444] (1) Synthesis of intermediate 222-1: N-(3-bromo-5-(tert-butyl)phenyl)-[1,1':3',1''-terphenyl]-2'-amine (1 eq), dibenzo[b,d]furan-2-ol (1.5 eq), CuI (0.1 eq), 2-pyridinecarboxylic acid (0.1 eq), and K2CO3 (3 eq) were dissolved in DMF and stirred at 160 °C for 12 hours. After cooling, the solvent was removed under reduced pressure and the mixture was washed with ethyl acetate and water. The organic layer was separated and dried with anhydrous MgSO4, followed by drying under reduced pressure. Intermediate 222-1 (yield: 62%) was obtained by column chromatography using MC and n-hexane as the developing solvent.

[0445] (2) Synthesis of Intermediate 222-2: Intermediate 222-1 (1 eq), intermediate 85-2 (1.3 eq), tris(dibenzylacetone)dipalladium (0) (0.15 eq), tri-tert-butylphosphine (0.3 eq), and sodium tert-butoxide (5 eq) were dissolved in o-xylene and stirred at 150 °C for 48 hours. After cooling, the solvent was removed under reduced pressure and the mixture was washed with ethyl acetate and water. The organic layer was separated and dried over anhydrous MgSO4, followed by drying under reduced pressure. Intermediate 222-2 (yield: 43%) was obtained by column chromatography using MC and n-hexane as the developing solvent.

[0446] (3) Synthesis of Compound 222: Intermediate 222-2 (1 equivalent) and 2,6-dichloropyridine (5 eq) were dissolved in o-dichlorobenzene in a flask, cooled to 0°C, and BBr3 (5 equivalent) was slowly injected under a nitrogen atmosphere. The temperature was then raised to 180°C and stirred for 24 hours. After cooling the mixture, triethylamine was slowly added dropwise to the flask to terminate the reaction, and then ethanol was added to the flask to obtain the product by precipitation and filtration. The obtained solid was purified by column chromatography using MC and n-hexane as the developing solvent, and then compound 222 (yield: 19%) was obtained by recrystallization from toluene and acetone.

[0447] Example 10: Synthesis of Compound 225

[0448] (1) Synthesis of intermediate 225-1: N-(5-bromo-[1,1'-biphenyl]-3-yl)-[1,1':3',1'-terphenyl]-2'-amine (1 eq), 1-phenylnaphth-2-ol (1.5 eq), CuI (0.1 eq), 2-pyridinecarboxylic acid (0.1 eq), and K2CO3 (3 eq) were dissolved in DMF and stirred at 160 °C for 24 hours. After cooling, the solvent was removed under reduced pressure and the mixture was washed with ethyl acetate and water. The organic layer was separated and dried with anhydrous MgSO4, followed by drying under reduced pressure. Intermediate 225-1 (yield: 55%) was obtained by column chromatography using MC and n-hexane as the developing solvent.

[0449] (2) Synthesis of Intermediate 225-2: Intermediate 225-1 (1 eq), intermediate 1-2 (1.3 eq), tris(dibenzylacetone)dipalladium (0) (0.15 eq), tri-tert-butylphosphine (0.3 eq), and sodium tert-butoxide (5 eq) were dissolved in o-xylene and stirred at 150 °C for 48 hours. After cooling, the solvent was removed under reduced pressure and the mixture was washed with ethyl acetate and water. The organic layer was separated and dried over anhydrous MgSO4, followed by drying under reduced pressure. Intermediate 225-2 (yield: 46%) was obtained by column chromatography using MC and n-hexane as the developing solvent.

[0450] (3) Synthesis of Compound 225: Intermediate 225-2 (1 equivalent) and 2,6-dichloropyridine (5 eq) were dissolved in o-dichlorobenzene in a flask, cooled to 0°C, and BBr3 (5 equivalent) was slowly injected under a nitrogen atmosphere. The temperature was then raised to 180°C and stirred for 24 hours. After cooling the mixture, triethylamine was slowly added dropwise to the flask to terminate the reaction, and then ethanol was added to the flask to obtain the product by precipitation and filtration. The obtained solid was purified by column chromatography using MC and n-hexane as the developing solvent, and then compound 225 (yield: 17%) was obtained by recrystallization from toluene and acetone.

[0451] Example 11: Synthesis of Compound 240

[0452] (1) Synthesis of Intermediate 240-1: N-([1,1':3',1''-terphenyl]-2'-yl)-4-bromodibenzo[b,d]furan-2-amine (1 eq), [1,1'-biphenyl]-3-ol (1.5 eq), CuI (0.1 eq), 2-pyridinecarboxylic acid (0.1 eq), and K2CO3 (3 eq) were dissolved in DMF and stirred at 160 °C for 24 h. After cooling, the solvent was removed under reduced pressure and the mixture was washed with ethyl acetate and water. The organic layer was separated and dried with anhydrous MgSO4, followed by drying under reduced pressure. Intermediate 240-1 (yield: 68%) was obtained by column chromatography using MC and n-hexane as the developing solvent.

[0453] (2) Synthesis of Intermediate 240-2: Intermediate 240-1 (1 eq), intermediate 1-2 (1.3 eq), tris(dibenzylacetone)dipalladium (0) (0.15 eq), tri-tert-butylphosphine (0.3 eq), and sodium tert-butoxide (5 eq) were dissolved in o-xylene and stirred at 150 °C for 48 hours. After cooling, the solvent was removed under reduced pressure and the mixture was washed with ethyl acetate and water. The organic layer was separated and dried over anhydrous MgSO4, followed by drying under reduced pressure. Intermediate 240-2 (yield: 50%) was obtained by column chromatography using MC and n-hexane as the developing solvent.

[0454] (3) Synthesis of Compound 240: Intermediate 240-2 (1 equivalent) and 2,6-dichloropyridine (5 eq) were dissolved in o-dichlorobenzene in a flask, cooled to 0°C, and BBr3 (5 equivalent) was slowly injected under a nitrogen atmosphere. The temperature was then raised to 180°C and stirred for 24 hours. After cooling the mixture, triethylamine was slowly added dropwise to the flask to terminate the reaction, and then ethanol was added to the flask to obtain the product by precipitation and filtration. The obtained solid was purified by column chromatography using MC and n-hexane as the developing solvent, and then compound 240 (yield: 15%) was obtained by recrystallization from toluene and acetone.

[0455] Example 12: Synthesis of Compound 271

[0456] (1) Synthesis of intermediate 271-1: N-(2-bromo-[1,1'-biphenyl]-4-yl)-[1,1':3',1''-terphenyl]-2'-amine (1 eq), [1,1'-biphenyl]-3-ol (1.5 eq), CuI (0.1 eq), 2-pyridinecarboxylic acid (0.1 eq), and K2CO3 (3 eq) were dissolved in DMF and stirred at 160 °C for 24 hours. After cooling, the solvent was removed under reduced pressure and the mixture was washed with ethyl acetate and water. The organic layer was separated and dried with anhydrous MgSO4, followed by drying under reduced pressure. Intermediate 271-1 (yield: 52%) was obtained by column chromatography using MC and n-hexane as the developing solvent.

[0457] (2) Synthesis of Intermediate 271-2: Intermediate 271-1 (1 eq), intermediate 1-2 (1.3 eq), tris(dibenzylacetone)dipalladium (0) (0.15 eq), tri-tert-butylphosphine (0.3 eq), and sodium tert-butoxide (5 eq) were dissolved in o-xylene and stirred at 150 °C for 48 hours. After cooling, the solvent was removed under reduced pressure and the mixture was washed with ethyl acetate and water. The organic layer was separated and dried over anhydrous MgSO4, followed by drying under reduced pressure. Intermediate 271-2 (yield: 41%) was obtained by column chromatography using MC and n-hexane as the developing solvent.

[0458] (3) Synthesis of Compound 271: Intermediate 271-2 (1 equivalent) and 2,6-dichloropyridine (5 eq) were dissolved in o-dichlorobenzene in a flask, cooled to 0°C, and BBr3 (5 equivalent) was slowly injected under a nitrogen atmosphere. The temperature was then raised to 180°C and stirred for 24 hours. After cooling the mixture, triethylamine was slowly added dropwise to the flask to terminate the reaction, and then ethanol was added to the flask to obtain the product by precipitation and filtration. The obtained solid was purified by column chromatography using MC and n-hexane as the developing solvent, and then compound 271 (yield: 16%) was obtained by recrystallization from toluene and acetone.

[0459] Compare Example 1 with p-DiNBO represented by the chemical formula.

[0460]

[0461] Comparative Examples 2 through 5 use compounds represented by chemical formulas.

[0462]

[0463] The light-emitting device is manufactured using an anode, on which a 15Ω / cm anode is formed. 2The glass substrate (Corning product) for the (1200Å) ITO electrode was cut to a size of 50mm × 50mm × 0.7mm, and the cut substrate was ultrasonically cleaned with isopropanol for 5 minutes, followed by ultrasonic cleaning with pure water. The ultrasonically cleaned substrate was irradiated with ultraviolet light for 30 minutes and then exposed to ozone before being mounted on a vacuum deposition apparatus.

[0464] Subsequently, compound HT3 was vacuum deposited on the anode to form a hole transport layer with a thickness of 600 Å. Compound HT47 was then vacuum deposited on the hole transport layer to form an electron blocking layer with a thickness of 100 Å.

[0465] A host compound, a phosphorescent compound (compound S1), and dopant compounds shown in Table 1, were co-deposited on the electron blocking layer at a weight ratio of 85:14:1 to form an emission layer with a thickness of 300 Å. The host compound, in which the first host (compound HTH1) and the second host (compound ETH26) were mixed in a weight ratio of 1:1, were also deposited on the electron blocking layer.

[0466] Compound ET46 was vacuum-deposited on the emitter layer to form a hole-blocking layer with a thickness of 50 Å, and compound ET47:LiQ (5:5 weight ratio) was vacuum-deposited to form an electron transport layer with a thickness of 300 Å. LiQ was then vacuum-deposited on the electron transport layer to form an electron injection layer with a thickness of 10 Å.

[0467] A light-emitting device is obtained by vacuum deposition of Al on the electron injection layer to form a cathode with a thickness of 1000 Å.

[0468] The following compounds are used to manufacture light-emitting devices.

[0469]

[0470] The evaluation example measures the properties of the light-emitting device using the following method, and the results are shown in Table 1.

[0471] For example, measurements were taken at 1000 cd / m² using a Keithley SMU 236 and a PR650 luminance meter. 2 The driving voltage (V), luminous efficiency (cd / A), maximum emission wavelength (nm), and device lifetime (T95) of the light-emitting device at the specified brightness.

[0472] In Table 1, device lifetime (T95) represents the time (h) until the brightness drops to 95% of its initial value. The relative value of the time measured in the light-emitting device using the compound of Comparative Example 1 is expressed as the lifetime (T95) of each light-emitting device in Table 1. For example, the lifetime (T95) of each light-emitting device in Table 1 is expressed as a relative value compared to the time measured in the light-emitting device using the compound of Comparative Example 1.

[0473] Table 1

[0474] Referring to Table 1, each of the example light-emitting devices provides a drive voltage of 3.6V or less and a luminous efficiency of 135cd / A or greater. Additionally, the example light-emitting devices offer a lifetime improvement of 8.3 times or more compared to Comparative Example 1.

[0475] In the light-emitting device of Comparative Example 1, which does not include the condensed heterocyclic compound of Formula 1 as a dopant, the luminous efficiency deteriorates and the lifetime is also significantly and substantially reduced.

[0476] When using compound C1 from Comparative Example 2, the driving voltage of the light-emitting device increases and the lifetime decreases. Compound C1 contains three nitrogen atoms and one oxygen atom surrounding (e.g., around the boron atom) in the multiresonant nucleus. The excess nitrogen atoms in compound C1 shallowen the HOMO level. Furthermore, the increased triplet exciton concentration due to exciton generation via direct trapping in the boron emitter leads to lifetime degradation. Even a slight increase in voltage causes hole trapping and also induces a slight long-wavelength shift. Therefore, high-purity green light dopant properties are not adequately provided.

[0477] Compound C2 in Comparative Example 3 exhibits weak binding properties due to the oxygen atom's central attachment to the para-position of the benzene ring. Therefore, it does not achieve sufficient green light emission. Compound C2 in Comparative Example 3 corresponds to a short-wavelength luminescent dopant that cannot be used as a green light dopant due to insufficient condensation structure around the nucleus.

[0478] Compound C3 in Comparative Example 4 has a structure in which the NBN side and OBO side are clearly separated. Therefore, in addition to multiple resonances (i.e., SRCT (short-range charge transfer), LRCT (long-range charge transfer) additionally occurs between NBN and OBO, thereby increasing the emission wavelength of the heterocyclic compound. Therefore, compound C3 cannot be used as a green light dopant due to chromatographic bias.

[0479] The color coordinate standards for display devices vary depending on the requirements for high color reproduction, such as the BT.2020 color coordinates and Adobe color coordinates, which exceed DCI-P3. In the case of green emitters, the maximum emission wavelength shifts from approximately 530 nm to approximately 520 nm. Compared to the wavelengths of compounds C1 to C4, the condensed heterocyclic compounds represented by Formula 1 can have wavelengths shortened by several nm, making deep green emission achievable and suitable for the aforementioned requirements.

[0480] In contrast, compound C4 of Example 5 has a biphenyl bonded to nitrogen instead of a terphenyl, thus failing to achieve sufficient intermolecular distance. Consequently, a slight long-wavelength shift occurs due to intermolecular interactions within the light-emitting device, and the DET suppression effect is insufficient to degrade the lifetime of the light-emitting device.

[0481] In this disclosure, it will be understood that if (for example, when) an element (or region, layer, and / or portion, etc.) is referred to as being "on" or "attached" to another element, it can be disposed directly on or directly attached to said other element, or an intervening element can be disposed therebetween. Conversely, "directly on" can mean that there is no additional layer, film, region, and / or plate, etc., between the layer, film, region, and / or plate, etc., and another portion. For example, "directly on" can mean that two layers or two components are disposed without utilizing any additional components (such as adhesive components) located therebetween.

[0482] As used herein, the terms “and / or” or “or” can include any and all combinations of one or more of the associated listed items. When expressions such as “at least one of…”, “one of…”, and “selected from…” precede / follow a list of elements, they modify the entire list of elements without modifying the individual elements of that list. For example, “at least one of a, b, and c”, “selected from a, b, and c”, and / or “selected from a to c” can mean only a, only b, only c, both a and b (e.g., simultaneously), both a and c (e.g., simultaneously), both b and c (e.g., simultaneously), all of a, b, and c, or variations thereof. The “ / ” used herein may be interpreted as “and” or “or” as appropriate.

[0483] It will be understood that while the terms “first” and / or “second” may be used herein to describe one or more suitable elements, components, regions, layers, and / or portions, these elements, components, regions, layers, and / or portions should not be limited by these terms. These terms are used only to distinguish one element, component, region, layer, or portion from another. Therefore, without departing from the scope of the disclosure, the first element, first component, first region, first layer, or first portion discussed herein may be referred to as a second element, second component, second region, second layer, or second portion, respectively. Similarly, the second element, second component, second region, second layer, or second portion may be referred to as a first element, first component, first region, first layer, or first portion, respectively. As used herein, unless the context clearly indicates otherwise, the singular forms “a,” “an,” “one,” and “the” are intended to include the plural forms as well. Furthermore, when describing embodiments of this disclosure, the use of “may” refers to “one or more embodiments of this disclosure.”

[0484] It will also be understood that if (for example, when) the terms “comprising,” “including,” and / or “having,” and variations thereof are used in this disclosure, it indicates the presence of the stated features, integrals, steps, operations, elements, components, and / or groups thereof, but does not preclude the presence or addition of one or more other features, integrals, steps, operations, elements, components, and / or groups thereof. Additionally, the terms “comprising,” “including,” “having,” or other similar terms include or support the terms “consisting of,” and “substantially consisting of,” indicating the presence of the stated features, integrals, steps, operations, elements, and / or components, while other features, integrals, steps, operations, elements, components, and / or groups thereof are absent or substantially absent.

[0485] Unless otherwise defined, all terms used herein (including technical and scientific terms) shall have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. It will also be understood that terms (such as those defined in a general dictionary) shall be interpreted as having a meaning consistent with their meaning in the context of the relevant field and shall not be interpreted in an idealized or overly formalized sense, unless expressly defined herein.

[0486] As used herein, the terms “substantially,” “about,” or similar terms are used as approximate terms rather than terms of degree and are intended to explain the inherent biases in measured or calculated values ​​that would be recognized by one of ordinary skill in the art. “About” as used herein includes the stated value and means within an acceptable range of deviation for a particular value as determined by one of ordinary skill in the art, taking into account the measurement in question and the errors associated with the measurement of the particular quantity (i.e., the limitations of the measurement system). For example, “about” may mean within one or more standard deviations, or within ±30%, ±20%, ±10%, or ±5% of the stated value.

[0487] In the context of this application, unless otherwise defined, the term “use” and its variations may be considered synonymous with the term “utilize” and its variations, respectively.

[0488] Any numerical range described herein is intended to include all subranges with the same numerical precision contained within the described range. For example, the range “1.0 to 10.0” is intended to include all subranges between the described minimum value 1.0 and the described maximum value 10.0 (and including both the described minimum value 1.0 and the described maximum value 10.0), i.e., having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as 2.4 to 7.6. Any maximum numerical limit described herein is intended to include all lower numerical limits contained therein, and any minimum numerical limit described in this specification is intended to include all higher numerical limits contained therein. Therefore, the applicant reserves the right to modify this disclosure (including the claims) to expressly describe any subranges contained within the expressly described range herein.

[0489] The light-emitting device, display device / apparatus, electronic device / electronic apparatus, apparatus for manufacturing thereof, or any other related device / apparatus or component according to embodiments of the present disclosure described herein can be implemented using any suitable hardware, firmware (e.g., application-specific integrated circuit), software, or a combination of software, firmware, and hardware. For example, various components of the apparatus can be formed on an integrated circuit (IC) chip or on separate IC chips. Furthermore, various components of the apparatus can be implemented on a flexible printed circuit film, a tape-on-a-chip (TCP), a printed circuit board (PCB), or formed on a substrate. Additionally, various components of the apparatus can be processes or threads that run on one or more processors in one or more computing devices, execute computer program instructions, and interact with other system components to perform the various functions described herein. The computer program instructions are stored in memory, which can be implemented in a computing device using standard memory devices, such as random access memory (RAM). The computer program instructions can also be stored in other non-transitory computer-readable media, such as CD-ROMs, flash drives, etc. Furthermore, those skilled in the art will recognize that, without departing from the scope of the embodiments of this disclosure, the functions of various computing devices may be combined or integrated into a single computing device, or the functions of a particular computing device may be distributed across one or more other computing devices.

[0490] In this disclosure, each suitable feature of the various embodiments disclosed may be combined in part or in whole, or combined with one another, and may be technically interlocked and operated in a variety of suitable ways, and unless otherwise stated or implied, each embodiment may be implemented independently of one another or in combination with one another in any suitable way.

[0491] While one or more embodiments have been described, it is understood that the disclosure is not intended to be limited to these embodiments, but rather that one or more suitable changes and modifications can be made by those skilled in the art within the spirit and scope of the claimed disclosure.

[0492] Therefore, the scope of the disclosed technology is not intended to be limited to what is set forth in the detailed description disclosed, but is intended to be defined by the appended claims and their equivalents.

Claims

1. A condensed heterocyclic compound, said condensed heterocyclic compound being represented by Chemical Formula 1: Chemical Formula 1 ,in, In Formula 1, X1 and X2 are both independently O, S, or Se, and R1 and R2 are both independently groups represented by Formula 2: Formula 2 In chemical formulas 1 and 2, R3 to R 10 Each group is independently hydrogen, deuterium, halogen, hydroxyl, cyano, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C3-C 60 Heterocyclic alkyl, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C8-C 60 Condensed polycyclic groups, -SiRR'R'', -P(=O)RR', -NRR', -BRR', -C(=O)R or -S(=O)2R; and optionally selected from R3 to R 10 Two or more of them combine with each other to form substituted or unsubstituted C3-C 60 Cycloalkyl ring, substituted or unsubstituted C5-C 60 Cycloalkenyl ring, substituted or unsubstituted C3-C 60 Heterocyclic alkyl rings, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl rings, substituted or unsubstituted C6-C 60 The aryl ring may be substituted or unsubstituted C2-C 60 A heteroaryl ring, wherein R, R', and R'' are each independently hydrogen, deuterium, halogen, hydroxyl, cyano, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C3-C 60 Heterocyclic alkyl, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthioyl or substituted or unsubstituted C8-C 60 A condensed polycyclic basis, where n, q, and s are all independent integers from 0 to 3, m and p are all independent integers from 0 to 4, r is an integer from 0 to 2, and t and u are all independent integers from 0 to 5. Indicates the junction point.

2. The condensed heterocyclic compound according to claim 1, wherein, The group represented by chemical formula 2 is represented by chemical formula 2-1 or chemical formula 2-2: Chemical formula 2-1 Chemical formula 2-2 Among them, in chemical formulas 2-1 and 2-2, R8 and R 10 , s and u are the same as R8 and R as defined in chemical formula 2 10 s and u are the same, R 11 and R 12 Each is independently hydrogen, deuterium, halogen, cyano, hydroxyl, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C3-C 60 Heterocyclic alkyl, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C8-C 60 Condensed polycyclic groups, -SiRR'R", -P(=O)RR', -NRR', -BRR', -C(=O)R or -S(=O)2R, where R, R' and R'' are the same as R, R' and R'' as defined in Formula 1 and Formula 2, and v and w are both independent integers from 0 to 5.

3. The condensed heterocyclic compound according to claim 1, wherein, The condensed heterocyclic compound is represented by one of chemical formulas 1-1 to 1-11: Chemical Formula 1-1 Chemical formula 1-2 Chemical formulas 1-3 Chemical formulas 1-4 Chemical formulas 1-5 Chemical formulas 1-6 Chemical formulas 1-7 Chemical formulas 1-8 Chemical formulas 1-9 Chemical formulas 1-10 Chemical formula 1-11 In chemical formulas 1-1 to 1-11, X1, X2, and R1 to R6 are the same as X1, X2, and R1 to R6 as defined in chemical formulas 1 and 2, and R... 31 To R 33 As described in R3, R 41 To R 44 As described in R4, R 51 To R 54 As described in R5, R 61 To R 63 As described in R6, R 71 and T 72 As described in R7, m' is 0 to 2, n' is 0 or 1, p' is 0 to 2, q' is 0 or 1, Y1 is C(Z1) or N, Y2 is C(Z2) or N, Y3 is C(Z3) or N, Y4 is C(Z4) or N, Y5 is C(Z5) or N, Y6 is C(Z6) or N, Y7 is C(Z7) or N, Y8 is C(Z8) or N, Y9 is C(Z9) or N, Y 10 It is C(Z) 10 ) or N, Y 11 It is C(Z) 11 ) or N, Y 12 It is C(Z) 12 ) or N, T1 to T4 are all independently single bonds, O, S or Se, and Z1 to Z 12 All are as described in R3.

4. The condensed heterocyclic compound according to claim 1, wherein, In chemical formula 1, at least two identical ones selected from R3 to R6 are present.

5. The condensed heterocyclic compound according to claim 1, wherein, In chemical formulas 1 and 2, R3 to R 10 Each is independently hydrogen, deuterium, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C6-C 20 aryl or substituted or unsubstituted C2-C 15 Mixed aromatic compounds.

6. The condensed heterocyclic compound according to claim 1, wherein, In chemical formula 1, n, m, p, and q are each independently 0, 1, or 2.

7. The condensed heterocyclic compound according to claim 1, wherein, In chemical formula 2, s, t, and u are all independently 0 or 1.

8. The condensed heterocyclic compound according to claim 1, wherein, In chemical formulas 1 and 2, R3 to R 10 Each is independently hydrogen, deuterium, or a C4-C electrode with or without deuteration. 15 Tertiary alkyl groups, substituted or unsubstituted phenyl groups, substituted or unsubstituted C7-C groups 20 Alkylphenyl, biphenyl substituted with or unsubstituted with deuterium, terphenyl substituted with or unsubstituted with deuterium, naphthyl substituted with or unsubstituted with deuterium, carbazolyl substituted with or unsubstituted with deuterium, dibenzofuranyl substituted with or unsubstituted with deuterium, or pyridyl substituted with or unsubstituted with deuterium.

9. The condensed heterocyclic compound according to claim 1, wherein, The condensed heterocyclic compound is selected from any of the compounds represented by the following chemical formulas: 。 10. A light-emitting device, the light-emitting device comprising: First electrode; Second electrode; and an intermediate layer between the first electrode and the second electrode, the intermediate layer comprising an emission layer comprising a condensed heterocyclic compound represented by Formula 1: Formula 1 In formula 1, X1 and X2 are both independently O, S, or Se, and R1 and R2 are both independently groups represented by formula 2: Formula 2 In chemical formulas 1 and 2, R3 to R 10 Each group is independently hydrogen, deuterium, halogen, hydroxyl, cyano, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C3-C 60 Heterocyclic alkyl, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C8-C 60 Condensed polycyclic groups, -SiRR'R'', -P(=O)RR', -NRR', -BRR', -C(=O)R or -S(=O)2R; and optionally selected from R3 to R 10 Two or more of them combine with each other to form substituted or unsubstituted C3-C 60 Cycloalkyl ring, substituted or unsubstituted C5-C 60 Cycloalkenyl ring, substituted or unsubstituted C3-C 60 Heterocyclic alkyl rings, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl rings, substituted or unsubstituted C6-C 60 The aryl ring may be substituted or unsubstituted C2-C 60 A heteroaryl ring, wherein R, R', and R'' are each independently hydrogen, deuterium, halogen, hydroxyl, cyano, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C3-C 60 Heterocyclic alkyl, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthioyl or substituted or unsubstituted C8-C 60 A condensed polycyclic basis, where n, q, and s are all independent integers from 0 to 3, m and p are all independent integers from 0 to 4, r is an integer from 0 to 2, and t and u are all independent integers from 0 to 5. Indicates the junction point.

11. The light-emitting device according to claim 10, wherein, The emission layer includes a host and a dopant, wherein the dopant includes the condensed heterocyclic compound as a thermally activated delayed fluorescence dopant.

12. The light-emitting device according to claim 11, wherein, The dopants also include phosphorescent dopants.

13. The light-emitting device according to claim 11, wherein, The main body comprises a hole transport entity represented by the chemical formula HT and an electron transport entity represented by the chemical formula ET: chemical formula HT In the chemical formula HT, L HT1 L HT2 and L HT3 Each is independently a direct bond, substituted or unsubstituted C6-C 30 aryl or substituted or unsubstituted C2-C 30 Hybrid aryl groups, lx1 to lx3 are all independent integers from 0 to 10, Ar HT1 and Ar HT2 Each is independently either substituted or unsubstituted C6-C 30 aryl or substituted or unsubstituted C2-C 30 heteroaryl, and Ar HT3 Is it substituted or unsubstituted C6-C? 30 Aryl, chemical formula ET In the chemical formula ET, X is selected from ET1 To X ET3 At least one of them is N, and X ET1 To X ET3 The rest of the components are all independently C(R) ET ), R ET It is hydrogen, deuterium, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C6-C 60 aryl or substituted or unsubstituted C2-C 60 Heteroaryl groups, lx1 to lx3 are all independent integers from 0 to 10, L ET1 To L ET3 Each is independently a direct bond, substituted or unsubstituted C6-C 30 aryl or substituted or unsubstituted C2-C 30 Hybrid aryl, and Ar ET1 To Ar ET3 Each is independently hydrogen, deuterium, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C6-C 30 aryl or substituted or unsubstituted C2-C 30 Mixed aromatic compounds.

14. The light-emitting device according to claim 13, wherein, The intermediate layer further includes: a hole transport layer between the emitter layer and the first electrode; and an electron transport layer between the emitter layer and the second electrode.

15. The light-emitting device according to claim 14, wherein, The intermediate layer further includes: an electron blocking layer between the hole transport layer and the emission layer; and a hole blocking layer between the emission layer and the electron transport layer.

16. The light-emitting device according to claim 15, wherein, The hole transport layer or the electron blocking layer comprises a compound represented by the chemical formula HT.

17. The light-emitting device according to claim 15, wherein, The electron transport layer or the hole blocking layer comprises a compound represented by the chemical formula ET.

18. The light-emitting device according to claim 10, wherein, The emission layer emits green light with a maximum emission wavelength in the range of 510 nm to 540 nm.

19. An electronic device, the electronic device comprising a light-emitting device, wherein, The light-emitting device includes: a first electrode; a second electrode; and an intermediate layer between the first electrode and the second electrode, the intermediate layer including an emitting layer comprising a condensed heterocyclic compound represented by Chemical Formula 1: Chemical Formula 1 In formula 1, X1 and X2 are both independently O, S, or Se, and R1 and R2 are both independently groups represented by formula 2: Formula 2 In chemical formulas 1 and 2, R3 to R 10 Each group is independently hydrogen, deuterium, halogen, hydroxyl, cyano, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C3-C 60 Heterocyclic alkyl, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C8-C 60 Condensed polycyclic groups, -SiRR'R'', -P(=O)RR', -NRR', -BRR', -C(=O)R or -S(=O)2R; and optionally selected from R3 to R 10 Two or more of them combine with each other to form substituted or unsubstituted C3-C 60 Cycloalkyl ring, substituted or unsubstituted C5-C 60 Cycloalkenyl ring, substituted or unsubstituted C3-C 60 Heterocyclic alkyl rings, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl rings, substituted or unsubstituted C6-C 60 The aryl ring may be substituted or unsubstituted C2-C 60 A heteroaryl ring, wherein R, R', and R'' are each independently hydrogen, deuterium, halogen, hydroxyl, cyano, substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 60 Cycloalkyl, substituted or unsubstituted C5-C 60 Cycloalkenyl, substituted or unsubstituted C3-C 60 Heterocyclic alkyl, substituted or unsubstituted C3-C 60 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthioyl or substituted or unsubstituted C8-C 60 A condensed polycyclic basis, where n, q, and s are all independent integers from 0 to 3, m and p are all independent integers from 0 to 4, r is an integer from 0 to 2, and t and u are all independent integers from 0 to 5. Indicates the junction point.

20. The electronic device according to claim 19, wherein, The electronic device is at least one of the following: flat panel display, curved display, computer monitor, medical monitor, television, billboard, indoor light, outdoor light, signal light, head-up display, fully transparent display, partially transparent display, flexible display, rollable display, foldable display, stretchable display, laser printer, telephone, mobile phone, tablet computer, tablet phone, personal information terminal, wearable device, laptop computer, digital camera, camcorder, viewfinder, microdisplay, 3D display, virtual reality display, augmented reality display, vehicle, video wall including multiple displays spliced ​​together, theater screen, stadium screen, phototherapy device, and signage.

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