Condensed heterocyclic compound, light emitting element and electronic device

Abstract

A condensed heterocyclic compound represented by Chemical Formula 1 is provided. A light-emitting element is provided, comprising a first electrode, a second electrode, and an intermediate layer disposed between the first electrode and the second electrode and comprising a light-emitting layer. The light-emitting layer comprises the condensed heterocyclic compound. An electronic device comprising the light-emitting element is provided.

Description

Technology Field

[0001] The embodiments of the present application relate to condensed heterocyclic compounds, light-emitting elements, and electronic devices. Background Technology

[0002] Organic light-emitting diodes possess self-luminous characteristics and can provide enhanced viewing angle and contrast characteristics. In addition, they can provide high response speed and high brightness.

[0003] An organic light-emitting device may include a light-emitting layer disposed between a first electrode and a second electrode. Holes moved from the first electrode and electrons moved from the second electrode may recombine in the light-emitting layer to generate excitons. As the excitons change from an excited state to a ground state, light-emitting characteristics are realized.

[0004] The above-described light-emitting layer may include a host material and a dopant material for implementing the light-emitting mechanism described above.

[0005] A boron-based multiple resonance TADF emitting material (DABNA) can be applied as the compound applied to the above-mentioned emitting layer. DABNA-based compounds exhibit TADF characteristics by separating HOMO and LUMO through multiple resonance between N and B atoms, thereby reducing the transition state energy difference.

[0006] Unlike conventional TADF materials, boron-based multiresonant TADF emitting materials (DABNA) exhibit high luminescence efficiency due to the large overlap between HOMO and LUMO. Additionally, they have excellent optical properties as the structural change before and after transition is small, resulting in low full width at half maximum (FWHM) and Stokes' shift. However, they have the disadvantage of a large efficiency roll-off when driven at high current densities due to the relatively large difference in transition state energy. The problem to be solved

[0007] One objective of the present disclosure is to provide a condensed heterocyclic compound having enhanced spectroscopic and luminescence properties.

[0008] One objective of the present disclosure is to provide a light-emitting element having improved light-emitting characteristics and reliability.

[0009] One objective of the present disclosure is to provide an electronic device including the light-emitting element. means of solving the problem

[0010] The condensed heterocyclic compound according to the present disclosure is represented by the following chemical formula 1.

[0011] [Chemical Formula 1]

[0012]

[0013] In Chemical Formula 1, R1 to R5 are the same or different from each other and each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, nitro group, substituted or unsubstituted C1-C 60 alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl groups, substituted or unsubstituted C1-C 60 alkoxy groups, substituted or unsubstituted C3-C 60 cycloalkyl groups, substituted or unsubstituted C5-C 60 cycloalkenyl groups of, substituted or unsubstituted C3-C 60 heterocycloalkyl groups, substituted or unsubstituted C3-C 60 heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 aryl groups, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 The aryloxy group of, substituted or unsubstituted C6-C 60 arylthio group of, substituted or unsubstituted C8-C 60A condensed polycyclic group, -SiRR'R", -P(=O)RR', -NRR', -BRR', -C(=O)R, or -S(=O)2R, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted C3-C 60 cycloalkyl ring, substituted or unsubstituted C5-C 60 cycloalkenyl ring of, substituted or unsubstituted C3-C 60 heterocycloalkyl ring of, substituted or unsubstituted C3-C 60 heterocycloalkenyl ring of, substituted or unsubstituted C6-C 60 aryl ring or substituted or unsubstituted C2-C 60 It forms a heteroaryl ring,

[0014] Q1 is a direct bond, O, NR, CRR', S, or Se, and

[0015] R, R', and R" are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, substituted or unsubstituted C1-C 60 alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl groups, substituted or unsubstituted C1-C 60 alkoxy groups, substituted or unsubstituted C3-C 60 cycloalkyl groups, substituted or unsubstituted C5-C 60 cycloalkenyl groups of, substituted or unsubstituted C3-C 60 heterocycloalkyl groups, substituted or unsubstituted C3-C 60 heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 aryl groups, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 The aryloxy group of, substituted or unsubstituted C6-C 60 arylthio group or substituted or unsubstituted C8-C 60It is a condensation polycyclic group, where r1 is an integer from 0 to 5, r2 is an integer from 0 to 4, r3 is an integer from 0 to 2, r4 is an integer from 0 to 6, r5 is an integer from 0 to 7, and when r1 to r5 are each 2 or more, multiple R1 to R5 are each independently identical or different from each other.

[0016] A light-emitting element according to the present disclosure comprises a first electrode, a second electrode, and an intermediate layer comprising a light-emitting layer disposed between the first electrode and the second electrode and comprising a condensed heterocyclic compound of Formula 1 described above.

[0017] The electronic device according to the present disclosure includes the light-emitting element described above. Effects of the invention

[0018] The condensed heterocyclic compound according to the embodiments of the present disclosure can suppress the degradation of the light-emitting device by maintaining the trigonal bond structure of the boron atom.

[0019] The above condensed heterocyclic compound has an aryl group, such as a phenyl group, substituted at the ortho position of a phenyl group directly bonded to a nitrogen atom, thereby relatively increasing the intermolecular distance. Consequently, the likelihood of intermolecular interactions that can reduce luminous efficiency, such as intermolecular aggregation, intermolecular excimer formation, or intermolecular exiplex formation, is relatively low. Therefore, the thermal stability of the light-emitting device is excellent.

[0020] In addition, the above-mentioned condensed heterocyclic compound can provide a light-emitting device having high color purity and high lifetime characteristics. Brief explanation of the drawing

[0021] FIGS. 1 to 6 are schematic cross-sectional views showing light-emitting elements according to exemplary embodiments. FIG. 7 is a schematic cross-sectional view showing a display device according to exemplary embodiments. FIG. 8 is a schematic cross-sectional view showing a display device according to exemplary embodiments. FIG. 9 is a schematic cross-sectional view showing a stacked form of a light-emitting structure in a display device according to exemplary embodiments. FIG. 10 is a schematic cross-sectional view showing a display device according to exemplary embodiments. FIG. 11 is a schematic cross-sectional view showing a display device according to exemplary embodiments. FIG. 12 is a schematic diagram showing an electronic device according to exemplary embodiments. FIG. 13 is a schematic diagram showing an electronic device according to exemplary embodiments. FIG. 14 is a block diagram of an electronic device according to one embodiment. FIG. 15 is a schematic diagram of an electronic device according to various embodiments. Specific details for implementing the invention

[0022] According to the present disclosure, a condensed heterocyclic compound represented by Formula 1 is provided. Additionally, a light-emitting element and an electronic device comprising said condensed heterocyclic compound are provided.

[0023] Definition of Terms

[0024] In this specification, "substituted or unsubstituted" refers, for example, a deuterium atom, a halogen atom, a cyano group, a nitro group, an amino group, a silyl group, an oxy group, a thio group, a sulfinyl group, a sulfonyl group, a carbonyl group, an ester group, a boron, a phosphine oxide group, a phosphine sulfide group, an alkyl group (for example, C1-C 60 , C1-C 10 alkyl groups), alkenyl groups (e.g., C2-C 60 , C2-C 10 alkenyl group), alkenyl group (e.g., C2-C 60 , C2-C 10 alkynyl group), alkoxy group (e.g., C1-C 60 , C1-C 10alkoxy groups), hydrocarbon ring groups, aryl groups (e.g., C6-C 60 aryl groups) and heterocyclic groups (e.g., C1-C 60 It may refer to one that is substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups. For example, "substituted alkyl group" may refer to one in which at least one of the hydrogen atoms of the alkyl group is substituted with the substituent described above, thereby further bonding a substituent to a carbon atom of the alkyl group.

[0025] The above substituent may include a combination selected from the groups described above. For example, at least one of the hydrogen atoms included as a substituent, such as an alkyl group or an aryl group, may be substituted with a deuterium atom, a halogen atom, a cyano group, a nitro group, an amino group, a silyl group, an oxy group, a thio group, a sulfinyl group, a sulfonyl group, a carbonyl group, an ester group, a boron, a phosphine oxide group, a phosphine sulfide group, an alkyl group, an alkenyl group, an alkynyl group, a hydrocarbon ring group, an aryl group, or a heterocyclic group.

[0026] Among the above substituents, multivalent substituents such as amino groups, phosphine sulfide groups, phosphine oxide groups, sulfinyl groups, sulfonyl groups, oxy groups, carbonyl groups, and ester groups are C1-C 10 alkyl group of, C1-C 10 alkenyl group of, C1-C 10 The alkynyl group or C6-C 10 It can be replaced by an aryl group.

[0027] The term "substituted or unsubstituted C" as used in this specification a -C b In the "Y period of", C a -C b refers to the number of carbon atoms of the unsubstituted Y group, and does not include the number of carbon atoms of the substituent.

[0028] An alkyl group refers to a monovalent hydrocarbon group from which one hydrogen atom has been removed from a straight-chain or branched-chain hydrocarbon group. For example, the alkyl group may include a methyl group, an ethyl group, a propyl group, a sec-butyl group, a tert-butyl group, an iso-butyl group, a pentyl group, a neopentyl group, a 2-ethylbutyl group, a 3,3-dimethylbutyl group, a hexyl group, a heptyl group, an octyl group, etc.

[0029] An alkylene group may refer to a divalent hydrocarbon group from which two hydrogen atoms have been removed from a straight-chain or branched-chain hydrocarbon group.

[0030] The alkenyl group may refer to a monovalent hydrocarbon group having the same skeleton as the alkyl group described above and having at least one of the bonds between carbon atoms as a double bond. The alkenylene group may refer to a divalent hydrocarbon group in which one additional hydrogen atom has been removed from the alkenyl group described above.

[0031] The alkynyl group may refer to a monovalent hydrocarbon group having the same skeleton as the alkyl group described above and having at least one of the bonds between carbon atoms as a triple bond. The alkynylene group may refer to a divalent hydrocarbon group in which one additional hydrogen atom has been removed from the alkynyl group described above.

[0032] An aryl group may refer to a monovalent hydrocarbon group from which one hydrogen atom has been removed from a hydrocarbon group having an aromatic structure. An aryl group may include a group in which multiple aromatic rings are directly connected, such as a biphenyl group. The aryl group may include, for example, a phenyl group, a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, fluorenyl group, tetracenyl group, biphenyl group, terphenyl group, quarterphenyl group, pyrenyl group, crisenyl group, etc.

[0033] Groups in which two or more aryl rings are condensed / connected to each other by a hydrocarbon ring, such as fluorenyl groups, are also included in the category of aryl groups.

[0034] For example, the biphenyl group can be interpreted as an aryl group, or as a phenyl group substituted with a phenyl group.

[0035] An arylene group can refer to a divalent hydrocarbon group from which two hydrogen atoms have been removed from an aryl group.

[0036] A heteroaryl group may refer to a monovalent group comprising at least one heteroatom such as B, O, P, S, and Si among the atoms forming a ring having an aromatic structure. A heteroarylene group may refer to a divalent group comprising at least one heteroatom such as B, O, P, S, and Si among the atoms forming a ring having an aromatic structure. When a heteroaryl group or a heteroarylene group comprises two or more heteroatoms, the two or more heteroatoms may be identical or different from each other.

[0037] Structures in which two or more aryls are condensed / connected by a non-aromatic heterocyclic ring, such as the carbazole group, are also included in the category of heteroaryls.

[0038] For example, "cyclic structure" can be used as a designation referring to both monocyclic and polycyclic structures, and alicyclic and aromatic rings.

[0039] "Polycyclic structure" may refer to a structure in which two or more rings are connected through one or more atoms. For example, polycyclic structures may include bicyclic structures, spiro structures, fused structures, etc., through bridge carbons.

[0040] "Condensation structure" or "condensed ring structure" may refer to a structure among the polycyclic structures described above in which two or more adjacent rings share two or more atoms. Examples of condensed ring structures include naphnalene, anthracene, phenanthrene, fluorene, pyrene, benzopyrene, pentacene, polyacene, helicene, etc.

[0041] Carbocyclic groups (e.g., C3-C 60 "Carbocyclic groups" refers to cyclic groups in which the ring-forming atoms are carbon. Heterocyclic groups (e.g., C1-C 60 A heterocyclic group refers to a cyclic group that includes a heteroatom as a ring-forming atom in addition to carbon.

[0042] Each of the above carbocyclic groups and heterocyclic groups may be a monocyclic group composed of one ring or a polycyclic group in which two or more rings are condensed together.

[0043] Condensed heterocyclic compounds

[0044] Condensed heterocyclic compounds according to exemplary embodiments are represented by the following chemical formula 1.

[0045] [Chemical Formula 1]

[0046]

[0047] In Chemical Formula 1, R1 to R5 are the same or different from each other and each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, nitro group, substituted or unsubstituted C1-C 60 alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl groups, substituted or unsubstituted C1-C 60 alkoxy groups, substituted or unsubstituted C3-C 60 cycloalkyl groups, substituted or unsubstituted C5-C 60 cycloalkenyl groups of, substituted or unsubstituted C3-C 60 heterocycloalkyl groups, substituted or unsubstituted C3-C 60 heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 aryl groups, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 The aryloxy group of, substituted or unsubstituted C6-C60 arylthio group of, substituted or unsubstituted C8-C 60 A condensed polycyclic group, -SiRR'R", -P(=O)RR', -NRR', -BRR', -C(=O)R, or -S(=O)2R, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted C3-C 60 cycloalkyl ring, substituted or unsubstituted C5-C 60 cycloalkenyl ring of, substituted or unsubstituted C3-C 60 heterocycloalkyl ring of, substituted or unsubstituted C3-C 60 heterocycloalkenyl ring of, substituted or unsubstituted C6-C 60 aryl ring or substituted or unsubstituted C2-C 60 It forms a heteroaryl ring,

[0048] Q1 is a direct bond, O, NR, CRR', S, or Se, and

[0049] R, R', and R" are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, substituted or unsubstituted C1-C 60 alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl groups, substituted or unsubstituted C1-C 60 alkoxy groups, substituted or unsubstituted C3-C 60 cycloalkyl groups, substituted or unsubstituted C5-C 60 cycloalkenyl groups of, substituted or unsubstituted C3-C 60 heterocycloalkyl groups, substituted or unsubstituted C3-C 60 heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 aryl groups, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 The aryloxy group of, substituted or unsubstituted C6-C 60 arylthio group or substituted or unsubstituted C8-C 60It is a condensed polycyclic group, and

[0050] r1 is an integer from 0 to 5, r2 is an integer from 0 to 4, r3 is an integer from 0 to 2, r4 is an integer from 0 to 6, r5 is an integer from 0 to 7, and if r1 to r5 are each 2 or more, multiple R1 to R5 are each independently identical or different from each other.

[0051] Boron-based multiple resonance TADF emitting materials (DABNA) series compounds, such as the compound represented by Chemical Formula 1 described above, have the advantages of high efficiency, a small full width at half maximum (FWHM), and a small Stokes' shift. However, boron atoms possess empty P orbitals, resulting in electron-deficient characteristics; furthermore, trivalent organo-boron compounds act as Lewis acids and can easily bond with nucleophiles (Lewis bases) or degradation substances within the device (e.g., radicals). In this case, boron atoms with a planar trigonal bonding structure transform into a tetrahedral structure, which can lead to degradation of device characteristics. Therefore, to protect the empty P orbitals of boron atoms, it is necessary to introduce substituents with large steric hindrance.

[0052] In addition, since boron-based multi-resonance TADF emitting materials (DABNA) series compounds have a plate-like structure, there is a high possibility of intermolecular interactions occurring within the device that can reduce luminescence efficiency, such as intermolecular aggregation, intermolecular excimer formation, or intermolecular exiplex formation. Therefore, it is necessary to introduce substituents to protect the core where the luminescence transition occurs.

[0053] The condensed heterocyclic compound represented by Chemical Formula 1 above includes an asymmetric core structure, thereby minimizing intermolecular aggregation, which can lower the sublimation temperature of the light-emitting device and provide high color purity. In addition, the condensed heterocyclic compound represented by Chemical Formula 1 includes a polycyclic heterocyclic structure as its core structure, which can induce a red-shift of the molecule and provide a deep HOMO.

[0054] In particular, the condensed heterocyclic compound represented by the above chemical formula 1 can induce a red-shift of the molecule by substituting a triazine group, which is a strong electron-withdrawing group (EWG), at the ortho position of the boron atom at the LUMO position of the core.

[0055] In the above chemical formula 1, the empty P orbital of the boron atom is effectively protected by a phenyl group substituted at the ortho position, so that the planar trigonal bonding structure of the boron atom can be stably maintained, thereby suppressing the degradation of the light-emitting device. In addition, the structure of the condensed heterocyclic compound represented by the above chemical formula 1 has a large steric hindrance, which relatively increases the distance between molecules, thereby relatively reducing the possibility of intermolecular interactions that can cause a decrease in luminous efficiency, such as intermolecular aggregation, intermolecular excimer formation, or intermolecular exciplex formation.

[0056] In addition, the condensed heterocyclic compound represented by the above chemical formula 1 exhibits high color purity, as the wavelength of the emission spectrum measured in solution and the emission spectrum measured from the deposited film are the same.

[0057] In addition, when fabricating a light-emitting device with a condensed heterocyclic compound represented by the above chemical formula 1, the approach of high-energy radicals, excitons, polarons, etc. is blocked, and Dexter energy transfer from the host / host and platinum-based sensitizer is suppressed, thereby reducing the degradation of the device and improving the lifespan of the device.

[0058] According to some embodiments, the above chemical formula 1 may be represented by the following chemical formula 1-1.

[0059] [Chemical Formula 1-1]

[0060]

[0061] In Chemical Formula 1-1, R1, R3 to R5, Q1, r1, and r3 to r5 are identical to the definitions in Chemical Formula 1, and R6 and R7 are identical or different from each other, and each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, nitro group, substituted or unsubstituted C1-C 60 alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl groups, substituted or unsubstituted C1-C 60 alkoxy groups, substituted or unsubstituted C3-C 60 cycloalkyl groups, substituted or unsubstituted C5-C 60 cycloalkenyl groups of, substituted or unsubstituted C3-C 60 heterocycloalkyl groups, substituted or unsubstituted C3-C 60 heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 aryl groups, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 The aryloxy group of, substituted or unsubstituted C6-C 60 arylthio group of, substituted or unsubstituted C8-C 60A condensed polycyclic group, -SiRR'R", -P(=O)RR', -NRR', -BRR', -C(=O)R, or -S(=O)2R, wherein two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C3-C 60 cycloalkyl ring, substituted or unsubstituted C5-C 60 cycloalkenyl ring of, substituted or unsubstituted C3-C 60 heterocycloalkyl ring of, substituted or unsubstituted C3-C 60 heterocycloalkenyl ring of, substituted or unsubstituted C6-C 60 aryl ring or substituted or unsubstituted C2-C 60 It forms a heteroaryl ring,

[0062] R, R', and R" are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, substituted or unsubstituted C1-C 60 alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl groups, substituted or unsubstituted C1-C 60 alkoxy groups, substituted or unsubstituted C3-C 60 cycloalkyl groups, substituted or unsubstituted C5-C 60 cycloalkenyl groups of, substituted or unsubstituted C3-C 60 heterocycloalkyl groups, substituted or unsubstituted C3-C 60 heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 aryl groups, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 The aryloxy group of, substituted or unsubstituted C6-C 60 arylthio group or substituted or unsubstituted C8-C 60 It is a condensed polycyclic group, and

[0063] r6 is an integer from 0 to 3, and

[0064] r7 is an integer from 0 to 5, and

[0065] If r6 and r7 are each 2 or more, multiple R6 and R7 are each independently identical or different from each other.

[0066] In some embodiments, the formula 1 may be represented by any one of the following formulas 2-1 to 2-4.

[0067] [Chemical Formula 2-1]

[0068]

[0069] [Chemical Formula 2-2]

[0070]

[0071] [Chemical Formula 2-3]

[0072]

[0073] [Chemical Formula 2-4]

[0074]

[0075] In Chemical Formulas 2-1 to 2-4, R1 to R5 and r1 to r5 are identical to the definitions in Chemical Formula 1, and

[0076] R8 is hydrogen, deuterium, halogen, hydroxyl group, cyano group, nitro group, substituted or unsubstituted C1-C 60 alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl groups, substituted or unsubstituted C1-C 60 alkoxy groups, substituted or unsubstituted C3-C 60 cycloalkyl groups, substituted or unsubstituted C5-C 60 cycloalkenyl groups of, substituted or unsubstituted C3-C 60 heterocycloalkyl groups, substituted or unsubstituted C3-C 60 heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 aryl groups, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60The aryloxy group of, substituted or unsubstituted C6-C 60 arylthio group of, substituted or unsubstituted C8-C 60 The condensation polycyclic group, -SiRR'R", -P(=O)RR', -NRR', -BRR', -C(=O)R or -S(=O)2R, and

[0077] Two or more adjacent C3-Cs combined with each other to form substituted or unsubstituted 60 cycloalkyl ring, substituted or unsubstituted C5-C 60 cycloalkenyl ring of, substituted or unsubstituted C3-C 60 heterocycloalkyl ring of, substituted or unsubstituted C3-C 60 heterocycloalkenyl ring of, substituted or unsubstituted C6-C 60 aryl ring or substituted or unsubstituted C2-C 60 It forms a heteroaryl ring,

[0078] R, R', and R" are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, substituted or unsubstituted C1-C 60 alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl groups, substituted or unsubstituted C1-C 60 alkoxy groups, substituted or unsubstituted C3-C 60 cycloalkyl groups, substituted or unsubstituted C5-C 60 cycloalkenyl groups of, substituted or unsubstituted C3-C 60 heterocycloalkyl groups, substituted or unsubstituted C3-C 60 heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 aryl groups, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 The aryloxy group of, substituted or unsubstituted C6-C 60 arylthio group or substituted or unsubstituted C8-C 60It is a condensed polycyclic group, and

[0079] R8 is an integer from 0 to 7, and

[0080] If R8 is 2 or more, multiple R8s are each independently identical or different from each other.

[0081] In some embodiments, the above chemical formula 1 may be represented by the following chemical formula 3-1.

[0082] [Chemical Formula 3-1]

[0083]

[0084] In Chemical Formula 3-1, R1 to R4, R5, Q1, r1 to r4, and r5 are the same as defined in Chemical Formula 1, and R9 and R 10 The atoms are the same or different from each other, and each independently consists of hydrogen, deuterium, substituted or unsubstituted C1-C atoms. 60 alkyl groups, substituted or unsubstituted C6-C 60 aryl groups or substituted or unsubstituted C2-C 60 It is a heteroaryl group of, or R9 and R 10 C2-C bonded together to form substituted or unsubstituted C2-C 60 It forms a heteroaryl ring.

[0085] In some embodiments, R1 is hydrogen, deuterium, or substituted or unsubstituted C6-C 60 It could be Arilgi.

[0086] In some embodiments, R1 is hydrogen, deuterium, or substituted or unsubstituted C6-C 50 It could be Arilgi.

[0087] In some embodiments, R1 is hydrogen, deuterium, or substituted or unsubstituted C6-C 40 It could be Arilgi.

[0088] In some embodiments, R1 is hydrogen, deuterium, or substituted or unsubstituted C6-C 30 It could be Arilgi.

[0089] In some embodiments, R1 is hydrogen, deuterium, or substituted or unsubstituted C6-C 20 It could be Arilgi.

[0090] In some embodiments, R1 is hydrogen, deuterium, or substituted or unsubstituted C6-C 10 It could be Arilgi.

[0091] In some embodiments, R1 may be hydrogen, deuterium, or a substituted or unsubstituted phenyl group.

[0092] In some embodiments, R1 may be hydrogen or a phenyl group.

[0093] In some embodiments, R1 may be hydrogen.

[0094] In some embodiments, R1 may be a phenyl group.

[0095] In some embodiments, R2 is hydrogen, deuterium, substituted or unsubstituted C1-C 60 alkyl groups or substituted or unsubstituted C6-C 60 It could be Arilgi.

[0096] In some embodiments, R2 is hydrogen, deuterium, substituted or unsubstituted C1-C 50 alkyl groups or substituted or unsubstituted C6-C 50 It could be Arilgi.

[0097] In some embodiments, R2 is hydrogen, deuterium, substituted or unsubstituted C1-C 40 alkyl groups or substituted or unsubstituted C6-C 40 It could be Arilgi.

[0098] In some embodiments, R2 is hydrogen, deuterium, substituted or unsubstituted C1-C 30 alkyl groups or substituted or unsubstituted C6-C 30 It could be Arilgi.

[0099] In some embodiments, R2 is hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl groups or substituted or unsubstituted C6-C 20 It could be Arilgi.

[0100] In some embodiments, R2 may be hydrogen, deuterium, a substituted or unsubstituted butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0101] In some embodiments, R2 may be hydrogen, deuterium, t-butyl group, phenyl group, or biphenyl group.

[0102] In some embodiments, R2 may be hydrogen, a t-butyl group, a phenyl group, or a biphenyl group.

[0103] In some embodiments, R2 may be hydrogen.

[0104] In some embodiments, R2 may be a t-butyl group.

[0105] In some embodiments, R2 may be a phenyl group.

[0106] In some embodiments, R2 may be a biphenyl group.

[0107] In some embodiments, R3 is hydrogen, deuterium, cyano group, substituted or unsubstituted C1-C 60 alkyl groups, substituted or unsubstituted C6-C 60 aryl groups, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 The aryloxy group, -SiRR'R" or -NRR', where R and R' are each independently hydrogen, deuterium, substituted or unsubstituted C1-C 60 alkyl groups or substituted or unsubstituted C6-C 60 It could be Arilgi.

[0108] In some embodiments, R3 is hydrogen, deuterium, cyano group, substituted or unsubstituted C1-C 50 alkyl groups, substituted or unsubstituted C6-C 50aryl groups, substituted or unsubstituted C2-C 50 heteroaryl groups, substituted or unsubstituted C6-C 50 The aryloxy group can be -SiRR'R" or -NRR'.

[0109] In some embodiments, R3 is hydrogen, deuterium, cyano group, substituted or unsubstituted C1-C 40 alkyl groups, substituted or unsubstituted C6-C 40 aryl groups, substituted or unsubstituted C2-C 40 heteroaryl groups, substituted or unsubstituted C6-C 40 The aryloxy group can be -SiRR'R" or -NRR'.

[0110] In some embodiments, R3 is hydrogen, deuterium, cyano group, substituted or unsubstituted C1-C 30 alkyl groups, substituted or unsubstituted C6-C 30 aryl groups, substituted or unsubstituted C2-C 30 heteroaryl groups, substituted or unsubstituted C6-C 30 The aryloxy group can be -SiRR'R" or -NRR'.

[0111] In some embodiments, R3 is hydrogen, deuterium, cyano group, substituted or unsubstituted C1-C 20 alkyl groups, substituted or unsubstituted C6-C 20 aryl groups, substituted or unsubstituted C2-C 20 heteroaryl groups, substituted or unsubstituted C6-C 20 The aryloxy group can be -SiRR'R" or -NRR'.

[0112] In some embodiments, R3 is hydrogen, deuterium, cyano group, substituted or unsubstituted C1-C 10 alkyl groups, substituted or unsubstituted C6-C 10 aryl groups, substituted or unsubstituted C2-C 10 heteroaryl groups, substituted or unsubstituted C6-C 10The aryloxy group can be -SiRR'R" or -NRR'.

[0113] In some embodiments, R3 may be hydrogen, deuterium, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted t-butyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted carbazole group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted phenyloxy group, -SiRR'R" or -NRR'.

[0114] In some embodiments, R3 may be a phenyl group, biphenyl group, terphenyl group, carbazole group, dibenzofuranyl group, phenyloxy group, -SiRR'R" or -NRR' substituted or unsubstituted with hydrogen, deuterium, cyano group, methyl group, t-butyl group, deuterium or carbazole group.

[0115] In some embodiments, where R3 is -SiRR'R" or -NRR', R, R' and R" are each independently substituted or unsubstituted C1-C 60 alkyl groups or substituted or unsubstituted C6-C 60 It could be Arilgi.

[0116] In some embodiments, where R3 is -SiRR'R" or -NRR', R, R' and R" are each independently substituted or unsubstituted C1-C 50 alkyl groups or substituted or unsubstituted C6-C 50 It could be Arilgi.

[0117] In some embodiments, where R3 is -SiRR'R" or -NRR', R, R' and R" are each independently substituted or unsubstituted C1-C 40 alkyl groups or substituted or unsubstituted C6-C 40 It could be Arilgi.

[0118] In some embodiments, where R3 is -SiRR'R" or -NRR', R, R' and R" are each independently substituted or unsubstituted C1-C 30 alkyl groups or substituted or unsubstituted C6-C 30 It could be Arilgi.

[0119] In some embodiments, where R3 is -SiRR'R" or -NRR', R, R' and R" are each independently substituted or unsubstituted C1-C 20 alkyl groups or substituted or unsubstituted C6-C 20 It could be Arilgi.

[0120] In some embodiments, where R3 is -SiRR'R" or -NRR', R, R' and R" are each independently substituted or unsubstituted C1-C 10 alkyl groups or substituted or unsubstituted C6-C 10 It could be Arilgi.

[0121] In some embodiments, where R3 is -SiRR'R" or -NRR', R, R' and R" may each be independently a substituted or unsubstituted methyl group or a substituted or unsubstituted phenyl group.

[0122] In some embodiments, where R3 is -SiRR'R" or -NRR', R, R' and R" may each independently be a methyl group or a phenyl group.

[0123] In some embodiments, R3 may be a phenyl group.

[0124] In some embodiments, R4 is hydrogen, deuterium, substituted or unsubstituted C1-C 60 alkyl groups, substituted or unsubstituted C6-C 60 aryl groups or substituted or unsubstituted C2-C 60 It is a heteroaryl group, or a C2-C in which two or more adjacent R4s are bonded to each other, resulting in substitution or non-substitution. 60 It can form a heteroaryl ring.

[0125] In some embodiments, R4 is hydrogen, deuterium, substituted or unsubstituted C1-C 50 alkyl groups, substituted or unsubstituted C6-C 50 aryl groups or substituted or unsubstituted C2-C 50 It is a heteroaryl group, or a C2-C in which two or more adjacent R4s are bonded to each other, resulting in substitution or non-substitution. 50 It can form a heteroaryl ring.

[0126] In some embodiments, R4 is hydrogen, deuterium, substituted or unsubstituted C1-C 40 alkyl groups, substituted or unsubstituted C6-C 40 aryl groups or substituted or unsubstituted C2-C 40 It is a heteroaryl group, or a C2-C in which two or more adjacent R4s are bonded to each other, resulting in substitution or non-substitution. 40 It can form a heteroaryl ring.

[0127] In some embodiments, R4 is hydrogen, deuterium, substituted or unsubstituted C1-C 30 alkyl groups, substituted or unsubstituted C6-C 30 aryl groups or substituted or unsubstituted C2-C 30 It is a heteroaryl group, or a C2-C in which two or more adjacent R4s are bonded to each other, resulting in substitution or non-substitution. 30 It can form a heteroaryl ring.

[0128] In some embodiments, R4 is hydrogen, deuterium, substituted or unsubstituted C1-C 20 alkyl groups, substituted or unsubstituted C6-C 20 aryl groups or substituted or unsubstituted C2-C 20 It is a heteroaryl group, or a C2-C in which two or more adjacent R4s are bonded to each other, resulting in substitution or non-substitution. 20 It can form a heteroaryl ring.

[0129] In some embodiments, R4 is hydrogen, deuterium, substituted or unsubstituted C1-C 10 alkyl groups, substituted or unsubstituted C6-C 10 aryl groups or substituted or unsubstituted C2-C 10 It is a heteroaryl group, or a C2-C in which two or more adjacent R4s are bonded to each other, resulting in substitution or non-substitution. 10 It can form a heteroaryl ring.

[0130] In some embodiments, R4 is hydrogen, deuterium, a substituted or unsubstituted butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group or a substituted or unsubstituted carbazole group, or two or more adjacent R4s may be combined to form a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzoselenophenyl group or a substituted or unsubstituted carbazole group.

[0131] In some embodiments, R4 is hydrogen, deuterium, t-butyl group, phenyl group, phenyl group substituted with t-butyl group, biphenyl group, terphenyl group, carbazole group, or carbazole group substituted with t-butyl group, or two or more adjacent R4s may be combined to form a dibenzofuranyl group, dibenzothiophenyl group, dibenzoselenophenyl group, or carbazole group substituted with phenyl group.

[0132] In some embodiments, R4 and R5 are each independently hydrogen, deuterium, a substituted or unsubstituted butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted carbazole group, or two or more adjacent groups may combine to form a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzoselenophenyl group.

[0133] In some embodiments, R5 is hydrogen, deuterium, substituted or unsubstituted C1-C 60 alkyl groups, substituted or unsubstituted C6-C 60 aryl groups or substituted or unsubstituted C2-C 60 It can be a heteroaryl group.

[0134] In some embodiments, R5 is hydrogen, deuterium, substituted or unsubstituted C1-C 50 alkyl groups, substituted or unsubstituted C6-C 50 aryl groups or substituted or unsubstituted C2-C 50 It can be a heteroaryl group.

[0135] In some embodiments, R5 is hydrogen, deuterium, substituted or unsubstituted C1-C 40 alkyl groups, substituted or unsubstituted C6-C 40 aryl groups or substituted or unsubstituted C2-C 40 It can be a heteroaryl group.

[0136] In some embodiments, R5 is hydrogen, deuterium, substituted or unsubstituted C1-C 30 alkyl groups, substituted or unsubstituted C6-C 30 aryl groups or substituted or unsubstituted C2-C 30 It can be a heteroaryl group.

[0137] In some embodiments, R5 is hydrogen, deuterium, substituted or unsubstituted C1-C 20 alkyl groups, substituted or unsubstituted C6-C 20 aryl groups or substituted or unsubstituted C2-C 20 It can be a heteroaryl group.

[0138] In some embodiments, R5 is hydrogen, deuterium, substituted or unsubstituted C1-C 10 alkyl groups, substituted or unsubstituted C6-C 10 aryl groups or substituted or unsubstituted C2-C 10 It can be a heteroaryl group.

[0139] In some embodiments, R5 may be hydrogen, deuterium, a substituted or unsubstituted butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazole group.

[0140] In some embodiments, R5 may be hydrogen, deuterium, t-butyl group, phenyl group, or carbazole group.

[0141] In some embodiments, R5 may be hydrogen or a t-butyl group.

[0142] In some embodiments, Q1 may be a direct bond.

[0143] In some embodiments, Q1 may be O.

[0144] In some embodiments, Q1 may be S.

[0145] In some embodiments, Q1 may be CRR', and R and R' may be hydrogen.

[0146] In some embodiments, the above chemical formula 1 may be any one of the following compounds.

[0147]

[0148]

[0149]

[0150]

[0151]

[0152] The degree of deuterium substitution of the condensed heterocyclic compound according to exemplary embodiments may be 0% to 100%. The "degree of deuterium substitution" may be a value calculated as a percentage of the number of deuterium atoms relative to the total sum of the number of hydrogen atoms and the number of deuterium atoms contained in the compound. For example, the degree of deuterium substitution of benzene with 5 deuterium atoms substituted may be about 83.33%.

[0153] The degree of deuterium substitution of the condensed heterocyclic compound according to some embodiments may be 1% to 100%, 5% to 100%, 20% to 100%, 30% to 100%, 40% to 100%, or 50% to 100%.

[0154] The degree of deuterium substitution of the condensed heterocyclic compound according to some embodiments may be 0% to 90%, 0% to 80%, 0% to 70%, 0% to 60%, or 0% to 50%.

[0155] According to exemplary embodiments, the condensed heterocyclic compound can be provided as a dopant to the light-emitting layer of a light-emitting device as described below.

[0156] According to exemplary embodiments, the condensed heterocyclic compound can be used as a green light-emitting dopant.

[0157] In some embodiments, the maximum emission wavelength of the green light may be 515 nm to 530 nm, 516 nm to 529 nm, 517 nm to 525 nm, or 518 nm to 521 nm.

[0158] Light-emitting element

[0159] FIGS. 1 to 6 are schematic cross-sectional views showing light-emitting elements according to exemplary embodiments.

[0160] Referring to FIG. 1, the light-emitting element (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 a light-emitting layer (130). The intermediate layer (ITL) may further include a hole transport region (120) and an electron transport region (140).

[0161] First electrode and second electrode

[0162] The first electrode (110) may be an anode or a cathode. In some embodiments, the first electrode (110) may be provided as an anode and may be provided as a pixel electrode. In this case, the first electrode (110) may include a high work function conductive material that promotes hole injection.

[0163] The first electrode (110) may be provided as a transparent electrode. The first electrode (110) may include a transparent conductive oxide such as ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), ITZO (indium tin zinc oxide), etc.

[0164] The first electrode (110) may be provided as a semi-transparent electrode or a reflective electrode. The first electrode (110) may include a metal selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, and Zn, or an alloy of two or more of these. For example, 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), a mixture of Ag and Mg, etc.

[0165] The first electrode (110) may have a single-layer structure or a multi-layer structure. For example, the first electrode (110) may have a three-layer structure of ITO / Ag / ITO.

[0166] The thickness of the first electrode (110) may be about 700 Å to about 10,000 Å or about 1,000 Å to about 3,000 Å.

[0167] The second electrode (150) may be provided as a cathode or an anode. In some embodiments, the second electrode (150) may be provided as an electron injection electrode or a cathode. The second electrode (150) may include a metal, alloy, electrically conductive compound, etc., having a low work function.

[0168] For example, the second electrode (150) may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO, etc. These may be used alone or in combination of two or more.

[0169] The second electrode (150) may be provided as a transparent electrode, a semi-transparent electrode, or a reflective electrode. The second electrode (150) may have a single-layer structure or a multi-layer structure.

[0170] light-emitting layer

[0171] The light-emitting layer (130) may include the above-described condensed heterocyclic compound.

[0172] According to exemplary embodiments, the light-emitting layer may include a host and a dopant.

[0173] According to exemplary embodiments, the condensed heterocyclic compound may be provided as a dopant. In one embodiment, the condensed heterocyclic compound may be provided as a fluorescent dopant. For example, the condensed heterocyclic compound may be provided as a Thermally Activated Delayed Fluorescence (TADF) dopant.

[0174] In one embodiment, the organometallic compound may be included as a green light-emitting dopant. For example, the organometallic compound may be included as a light-emitting material having a light-emitting center wavelength in the wavelength range of 515 nm to 530 nm.

[0175] In some embodiments, the light-emitting layer (130) may include a host material represented by, for example, the following chemical formula PH. For example, a compound represented by the chemical formula PH may be used as a host material for a phosphorescent light-emitting layer or a phosphorescent light-emitting device.

[0176] [Chemical Formula PH]

[0177]

[0178] In the chemical formula pH, R PH may be a substituted or unsubstituted carbazole group. L PH C6-C6 with direct bonding, substitution, or non-substitution 30 Aryllene group, or substituted or unsubstituted C2-C 30 It can be a heteroarylene group. Ar PH C6-C with substituted or unsubstituted components 30 Aryl group, substituted or unsubstituted C2-C 30 It can be a heteroaryl group.

[0179] As mentioned in the definition of terms, "C6-C 30 The term "aryl group" is used to encompass structures in which multiple aryls are condensed or bonded through a cyclic group (e.g., an alicyclic hydrocarbon ring). For example, C6-C 30 An aryl group can encompass a fluorenyl group.

[0180] As mentioned in the definition of terms, "C2-C 30 The term "heteroaryl group" is used to encompass structures in which multiple aryls are condensed or bonded through a heterocyclic ring. For example, C2-C 30Heteroaryl groups can encompass carbazole groups, dibenzofuran groups, dibenzothiophen groups, etc. In addition, C2-C 30 The term heteroaryl group is used to encompass a structure in which multiple aryls are condensed or bonded to one another through identical or different heterocyclic rings.

[0181] In one embodiment, Ar PH The substituents included in may include silyl groups. The silyl group is -Si(R sa )(R sb )(R sc It is indicated by ), and R sa , R sb and R sc Each independently consists of hydrogen, halogen, hydroxyl group, and C1-C 60 Alkyl group, C1-C 60 Alkoxy group, C6-C 60 aryl group, or C2-C 30 It can be a heteroaryl group. R sa , R sb and R sc At least one of them is C6-C 60 aryl group or C2-C 30 It can be a heteroaryl group. R sa , R sb and R sc Each independently C6-C 60 aryl group or C2-C 30 It can be a heteroaryl group.

[0182] lx can be an integer from 0 to 10 or more. If lx is an integer of 2 or more, multiple L PH They may be the same or different from each other.

[0183] 발광층(130)은 호스트 물질로서, 예를 들면, BCPDS (bis (4-(9H-carbazol-9-yl) phenyl) diphenylsilane), POPCPA ((4-(1-(4-(diphenylamino) phenyl) cyclohexyl) phenyl) diphenyl-phosphine oxide), DPEPO(bis[2-(diphenylphosphino)phenyl] ether oxide), mCBP(3,3'-Di(9H-carbazol-9-yl)-1,1'-biphenyl), CBP(4,4'-bis(N-carbazolyl)-1,1'-biphenyl), mCP(1,3-bis(carbazol-9-yl)benzene), PPF(2,8-bis(diphenylphosphoryl)dibenzo[b,d]furan), TCTA(4,4',4''-Tris(carbazol-9-yl)-triphenylamine), TPBi(1,3,5-tris(1-phenyl-1H-benzo[d]imidazole-2-yl)benzene), Alq3(tris(8-hydroxyquinolino)aluminum), ADN(9,10-di(naphthalene-2-yl)anthracene), TBADN(2-tert-butyl-9,10-di(naphth-2-yl)anthracene), DSA(distyrylarylene), CDBP(4,4′-bis(9-carbazolyl)-2,2′-dimethyl-biphenyl), MADN(2-methyl-9,10-bis(naphthalen-2-yl)anthracene), CP1(mexaphenyl cyclotriphosphazene), UGH2 (1,4-bis(triphenylsilyl)benzene), DPSiO3 (hexaphenylcyclotrisiloxane), DPSiO4 (octaphenylcyclotetrasiloxane) 등을 포함할 수도 있다.

[0184] The aforementioned host materials may be used alone or in combination of two or more.

[0185] The light-emitting layer (130) may further include a dopant that interacts with the host described above.

[0186] In some embodiments, the light-emitting layer (130) may include a dopant represented by the following chemical formula FD. For example, a compound represented by the following chemical formula FD may be used as a fluorescent dopant.

[0187] [Chemical Formula FD]

[0188]

[0189] In the chemical formula FD, Ar FD , R FD1 and R FD2 Each is independently substituted or unsubstituted C3-C 60 Carbocyclic groups, or substituted or unsubstituted C1-C 60 It may be a heterocyclic group. Ax may be an integer from 1 to 6.

[0190] In some embodiments, Ar FD It may include a condensed ring structure of three or more aryl rings or benzene rings (e.g., anthracene group, chrysene group, pyrene group, etc.).

[0191] In some embodiments, the light-emitting layer (130) may include a phosphorescent dopant. For example, the dopant may further include a phosphorescent dopant. The phosphorescent dopant may include an organometallic compound comprising a central metal and at least one ligand coordinately bonded to the central metal. The central metal may include, for example, a transition metal, and the ligand may include, for example, a monodenate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or a combination thereof.

[0192] The above phosphorescent dopant may include, for example, a compound represented by the chemical formula PD.

[0193] [Chemical PD]

[0194] M(L d 1 ) dx1 (L d 2 ) dx2

[0195] Among the chemical formula PD,

[0196] M can be a transition metal atom, for example, 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).

[0197] L d 1 may be a ligand represented by the following chemical formula LD1.

[0198] [Chemical Formula LD1]

[0199]

[0200] In the chemical formula LD1, X PD1 and X PD2Each can be independently C or N.

[0201] In one embodiment, X PD1 and X PD2 One of them may be C and the other may be N. In one embodiment, X PD1 and X PD2 All can be N.

[0202] CG PD1 and CG PD2 Each is independently substituted or unsubstituted C3-C 60 Carbocyclic groups, or substituted or unsubstituted C1-C 60 It may be a heterocyclic group. CG PD1 and CG PD2 For example, each independently pyrrole group, pyrazol group, imidazole group, triazole group, oxazole group, isooxazole group, thiazole group, isothiaazole group, oxadiazole group, thiadiazole group, benzene group, pyridine group, pyrimidine group, naphthalene group, dibenzofuran group, dibenzothiophen group, carbazole group, fluorene group, dibenzocilol group, naphthobenzofuran group, naphthobenzothiophen group, benzocarbazole group, benzoffluorene group, naphthobenzocilol group, dinaphthofuran group, dinaphthiophen group, dibenzocarbazole group, dibenzoffluorene group, dinaphthiophenol group, azadibenzofuran group, azadibenzothiophen group, azacarbazole group, azafluorene group, azadibenzocilol group, It may be an azanaphthofenzofuran group, an azanaphthofenzothiophene group, an azabenzocarbazole group, an azabenzoflurene group, an azanaphthofenzosilol group, an azadinafthofenzofuran group, an azadinafthofenzothiophene group, an azadibenzocarbazole group, an azadibenzoflurene group, or an azadinaftholol group.

[0203] L PD is a single bond, a substituted or unsubstituted methylene group, a substituted or unsubstituted ethenyllene group, *-O-*', *-S-*', *-C(=O)-*', *-N(R PD3)-*', *-C(R PD4 )=*' or *=C(R PD5 )=*'can be.

[0204] X PD3 and X PD4 Each is independently chemically bonded, O, S, N(R PD6 ), B(R PD7 ), P(R PD8 ), C(R PD9 )(R PD10 ) or Si(R PD11 )(R PD12 It can be. Chemical bonds can be, for example, covalent bonds or coordinate bonds.

[0205] R PD1 and R PD2 Each is independently hydrogen, deuterium, -F, -Cl, -Br, -I, -OH, -CN, -NO2, substituted or unsubstituted C1-C 60 alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl groups, substituted or unsubstituted C1-C 60 alkoxy groups, substituted or unsubstituted C3-C 60 cycloalkyl groups, substituted or unsubstituted C5-C 60 cycloalkenyl groups of, substituted or unsubstituted C3-C 60 heterocycloalkyl groups, substituted or unsubstituted C3-C 60 heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 aryl groups, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 The aryloxy group of, substituted or unsubstituted C6-C 60 arylthio group of, substituted or unsubstituted C8-C 60 Condensed polycyclic group, substituted or unsubstituted silyl group, substituted or unsubstituted amine group, substituted or unsubstituted aniline group, -B(R PD13 )(R PD14), -C(=O)(R PD15 ), -S(=O)2(R PD16 ), or -P(=O)(R PD17 )(R PD18 It can be ). The definition of a silyl group is -Si(R sa )(R sb )(R sc Refer to the definition of ).

[0206] R PD3 to R PD18 Each is independently hydrogen, deuterium, -F, -Cl, -Br, -I, -OH, -CN, -NO2, substituted or unsubstituted C1-C 60 alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl groups, substituted or unsubstituted C1-C 60 alkoxy groups, substituted or unsubstituted C3-C 60 cycloalkyl groups, substituted or unsubstituted C5-C 60 cycloalkenyl groups of, substituted or unsubstituted C3-C 60 heterocycloalkyl groups, substituted or unsubstituted C3-C 60 heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 aryl groups, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 The aryloxy group of, substituted or unsubstituted C6-C 60 The arylthio group of, or substituted or unsubstituted C8-C 60 It can be a condensed polycyclic group.

[0207] cx1 and cx2 are each independently integers from 0 to 10, and if at least one of them is 2 or more, multiple R PD1 or multiple R PD2 They may be the same or different from each other.

[0208] -* and -*` are binding sites where the ligand represented by the chemical formula LD1 binds to M.

[0209] dx1 is an integer from 1 to 3. For example, if dx1 is 2 or 3, multiple L d 1 They may be identical or different from each other. Multiple L d 1 Among them, mutually adjacent CGs PD1 and / or CG PD2 is L PD1 , L PD2 They can be connected to each other through connectors such as L. PD1 , L PD2 The definition of a connector for the back is L PD Refer to the definition of.

[0210] L d 2 can be an organic ligand. L d 2 It may include, for example, a halogen group, CO, NO, CS, picolinate, acetate, oxalate, diketone group, isonitrile group, isothiocyanato-N, thiosulfato-S, alkylphosphine, phenylphosphine, arylphosphine, phosphine oxide, phosphite, or a combination thereof.

[0211] dx2 is an integer from 1 to 4. For example, if dx2 is 2 or greater, multiple L d 2 They may be the same or different from each other.

[0212] In some embodiments, the light-emitting layer (130) is a fluorescent dopant material, styryl derivative (e.g., 1,4-bis[2-(3-N-ethylcarbazoryl)vinyl]benzene (BCzVB), 4-(di-p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl)naphthalen-2-yl)vinyl)phenyl)-N-phenylbenzenamine (NBDAVBi), 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi), perylene and its derivatives (e.g., 2,5,8,11-tetra-t-butylperylene (TBP)), pyrene and its derivatives (e.g., It may include 1,1-dipyrene, 1,4-dipyrenylbenzene, 1,4-bis(N,N-diphenylamino)pyrene, etc.

[0213] The light-emitting layer (130) may include a metal complex comprising iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm) as a phosphorescent dopant in addition to the materials described above. For example, FIrpic (iridium(III) bis(4,6-difluorophenylpyridinato-N,C2')picolinate), FIr6 (Bis(2,4-difluorophenylpyridinato)-tetrakis(1-pyrazolyl)borate iridium(III)), PtOEP (platinum octaethyl porphyrin), etc., may be used as a phosphorescent dopant.

[0214] In some embodiments, the light-emitting layer (130) may include a boron-containing dopant. The boron-containing dopant may be represented by the following chemical formula BD.

[0215] [Chemical Formula BD]

[0216]

[0217] Among the chemical formula BD, X BD1 and X BD2 Each can independently be N, S, O, or C. In one embodiment, X BD1 and X BD2 can be N. R BD1 and R BD2 Each is independently hydrogen, deuterium, substituted or unsubstituted C1-C 20 Alkyl groups, substituted or unsubstituted C6-C 30 Aryl groups, or substituted or unsubstituted C2-C 30 It can be a heteroaryl group. R BD3 , R BD4 and R BD5 Each independently consists of hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted amine group, substituted or unsubstituted boryl group, substituted or unsubstituted oxy group, substituted or unsubstituted thio group, substituted or unsubstituted C1-C 20 Alkyl groups, substituted or unsubstituted C6-C 30 Aryl groups, or substituted or unsubstituted C2-C 30 It can be a heteroaryl group. R BD3 , R BD4 and / or R BD5 It can combine with adjacent tiles to form a ring.

[0218] CG BD1 and CG BD2 represents a cyclic group, each independently, a substituted or unsubstituted C3-C 60 Carbocyclic groups, or substituted or unsubstituted C1-C 60 It may be a heterocyclic group. In some embodiments, CG BD1 and CG BD2 Each is independently substituted or unsubstituted C6-C 30 Aryl groups, or substituted or unsubstituted C2-C30 It can be a heteroaryl group.

[0219] In one embodiment, CG BD1 and CG BD2 Each may be an independently substituted or unsubstituted phenyl group. In this case, the boron-containing dopant may be provided as a heat-activated delayed fluorescence (TADF) dopant.

[0220] In one embodiment, CG BD1 and CG BD2 One of them may be a non-condensing aryl group or a non-condensing heteroaryl group, and the other may be a condensing polycyclic aryl group or a condensing polycyclic heteroaryl group. In this case, the boron-containing dopant may be provided as a fluorescent dopant.

[0221] The above-described dopant materials can be used alone or in combination of two or more.

[0222] In some embodiments, the light-emitting layer (130) may include two or more host materials. For example, the light-emitting layer (130) may include a hole-transporting host and an electron-transporting host. In this case, the light-emitting layer (130) may include a hole-transporting host, an electron-transporting host, a photosensitive material, and a dopant. According to exemplary embodiments, the hole-transporting host and the electron-transporting host form an exciplex, and an energy transfer occurs from the exciplex to the photosensitive material, and from the photosensitive material to the dopant, thereby inducing light emission.

[0223] In some embodiments, the hole-transporting host may include a compound of the formula HT described below. In some embodiments, the electron-transporting host may include a compound represented by the formula ET described below. For example, the host may include a hole-transporting host represented by the formula HT and an electron-transporting host represented by the formula ET.

[0224] In some embodiments, the light-emitting layer (130) may include quantum dots. The quantum dots may include a Group II-VI compound, a Group III-VI compound, a Group I-III-VI compound, a Group III-V compound, a Group III-II-V compound, a Group IV-VI compound, a Group IV element, a Group IV compound, or a combination thereof.

[0225] The above quantum dot comprises a core containing the aforementioned compound and may include a shell surrounding the core. The shell may include an inorganic oxide or a semiconductor compound. The semiconductor compound may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, etc.

[0226] For example, the color of the emitted light can be controlled according to the particle size of the above quantum dots. The above quantum dots can be classified into blue quantum dots, red quantum dots, green quantum dots, etc.

[0227] Hole transmission zone

[0228] A hole transport region (120) may be formed between the first electrode (110) and the light-emitting layer (130). The hole transport region (120) may have a single layer or a multilayer structure comprising a plurality of layers each containing different materials.

[0229] The hole transport region (120) may include a hole injection layer, a hole transport layer and / or an electron blocking layer, and may further include a light-emitting auxiliary layer.

[0230] In some embodiments, as shown in FIG. 2, 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).

[0231] In some embodiments, as illustrated in FIG. 3, 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 electron movement from the electron transport region (140) to the hole transport region (120). Thus, exciton generation in the light-emitting layer (130) can be increased, and the light emission efficiency can be further increased.

[0232] For example, the hole transport region (120) may include a compound represented by the following chemical formula HT.

[0233] [Chemical Formula HT]

[0234]

[0235] In the chemical formula HT, L HT1 , L HT2 and L HT3 Each is independently directly linked, substituted, or unsubstituted C6-C 30 Aryllene group, or substituted or unsubstituted carbon 2-C 30 It can be a heteroarylen group.

[0236] lx1 to lx3 may each independently be an integer between 0 and 10. If lx1, lx2, or lx3 is an integer of 2 or more, multiple L HT1 and L HT2 For example, they are directly connected by carbon atoms of each aryl ring (e.g., sp2 carbons), and each is independently substituted or unsubstituted C6-C 30 Aryllene group, or substituted or unsubstituted carbon 2-C 30 It can be a heteroarylen group.

[0237] Ar HT1 and Ar HT2 Each independently, substituted or unsubstituted C6-C 30 Aryl groups, or substituted or unsubstituted C2-C30 It can be a heteroaryl group. Ar HT3 C6-C with substituted or unsubstituted components 30 It could be Arilgi.

[0238] In one embodiment, the compound represented by the chemical formula HT may be a monoamine compound. In one embodiment, the compound represented by the chemical formula HT is Ar HT1 or Ar HT3 At least one of them may be a diamine compound containing an amine group as a substituent.

[0239] In some embodiments, the compound represented by the chemical formula HT is Ar HT1 and Ar HT2 A carbazole compound comprising a carbazole group substituted or unsubstituted in at least one of the following, or Ar HT1 and Ar HT2 It may be a fluorene-based compound comprising a substituted or unsubstituted fluorene group in at least one of them.

[0240] In some embodiments, Ar HT1 or Ar HT3 Two adjacent groups may condense to form a single ring.

[0241] For example, the hole transport region 120 includes 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(naphthalene-l-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 ,N1' -([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -phenyl-N 4 ,N 4 -di-m-tolylbenzene-1,4-diamine), TAPC (4,4'-cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine]), 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 / Camphor sulfonicacid), PANI / PSS (polyaniline / poly(4-styrenesulfonate)), phthalocyanine-based compounds, carbazole-based compounds It may include compounds (9-(4-tert-butylphenyl)-3,6-ditrityl-9H-carbazole, N-phenylcarbazole, polyvinylcarbazole, etc.), fluorene-based compounds, etc. These may be used alone or in combination of two or more.

[0242] The above-described material may be included in at least one layer among the hole injection layer (122), the hole transport layer (124), and the electron blocking layer (126).

[0243] The hole transport region (120) may further include a charge generating material. A dopant material such as a p-dopant may be used as the charge generating material, and accordingly, the conductivity of the hole transport region (120) may be improved.

[0244] For example, examples of the above dopant materials include metal halide compounds such as LiF, NaCl, CsF, RbCl, RbI, CuI, and KI; quinone derivatives such as TCNQ (Tetracyanoquinodimethane) and F4-TCNQ (2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane); cyano-containing compounds such as HATCN (dipyrazino[2,3-f: 2',3'-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile) and NDP9 (4-[[2,3-bis[cyano-(4-cyano-2,3,5,6-tetrafluorophenyl)methylidene]cyclopropylidene]-cyanomethyl]-2,3,5,6-tetrafluorobenzonitrile); W oxide, Mo oxide, etc. These can be used individually or in combination of two or more.

[0245] The thickness of the hole transport region (120) can be about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,500 Å.

[0246] When the hole transport region (120) includes a hole injection layer (122) and a hole transport layer (124), the thickness of the hole injection layer (122) may be about 100 Å to about 9000 Å, about 100 Å to about 3000 Å, or about 100 Å to about 1000 Å, and the thickness of the hole transport layer (124) may be about 50 Å to about 2000 Å, about 100 Å to about 1500 Å, about 100 Å to about 1000 Å, or about 100 Å to about 600 Å.

[0247] In the above thickness range, hole transport characteristics are enhanced even at low voltage driving, and the lifespan of the device can be further improved.

[0248] Each layer of the hole transport region (120) can be formed through processes such as vacuum deposition, spin coating, inkjet printing, laser printing, casting, laser thermal transfer, etc.

[0249] Electron transfer region

[0250] An electron transfer region (140) may be formed between the second electrode (150) and the light-emitting layer (130). The electron transfer region (140) may have a single layer or a multilayer structure comprising a plurality of layers each containing different materials.

[0251] The electron transport region (140) may include an electron injection layer, an electron transport layer and / or a hole blocking layer, and may further include a light-emitting auxiliary layer.

[0252] In some embodiments, as shown in FIG. 2, the electron transfer region (140) may include an electron injection layer (142) and an electron transport layer (144) sequentially stacked from the second electrode (150) toward the light-emitting layer (130).

[0253] In some embodiments, as illustrated in FIG. 3, the electron transfer region (140) may include an electron injection layer (142), an electron transport layer (144), and a hole blocking layer (146) sequentially stacked from the second electrode (150). The injection of holes from the hole transfer region (120) may be suppressed or blocked by the hole blocking layer (146). Thus, the emission energy and luminescence efficiency in the light-emitting layer (130) may be further improved.

[0254] For example, the hole transport region (120) may include a compound represented by the following chemical formula ET.

[0255] [Chemical Formula ET]

[0256]

[0257] In the chemical formula ET, X ET1 To X ET3At least one of them is N and the others are each independently CR ET It could be. R ET is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted C1-C 20 Alkyl groups, substituted or unsubstituted C6-C 60 Aryl groups, or substituted or unsubstituted C2-C 60 It can be a heteroaryl group.

[0258] X ET1 To X ET3 If either one is N, the compound represented by the chemical formula ET may contain a pyridine group. X ET1 To X ET3 If either of the two are N, the compound represented by the chemical formula ET may contain a pyrimidine group. X ET1 To X ET3 When all of these are N, the compound represented by the chemical formula ET may contain a triazine group.

[0259] lx1 to lx3 can each independently be an integer from 0 to 10. L ET1 to L ET3 Each is independently a directly linked, substituted, or unsubstituted C6-C 30 Aryllene group, or substituted or unsubstituted C2-C 30 It can be a heteroarylen group.

[0260] If lx1, lx2, or lx3 is an integer greater than or equal to 2, multiple L ET1 L ET2 S, or L ET3 For example, they are directly connected by carbon atoms of each aryl ring (e.g., sp2 carbons), and each is independently substituted or unsubstituted C6-C 30 Aryllene group, or substituted or unsubstituted carbon 2-C 30 It can be a heteroarylen group.

[0261] Ar ET1 or Ar ET3Each is independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted C1-C 20 Alkyl groups, substituted or unsubstituted C6-C 30 Aryl groups, or substituted or unsubstituted C2-C 30 It can be a heteroaryl group. For example, Ar ET1 or Ar ET3 Each may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted fluorene group, or a substituted or unsubstituted silyl group. The definition of a silyl group is -Si(R sa )(R sb )(R sc Refer to the definition of ).

[0262] For example, the electron transfer region (140) is an anthracene compound, Alq3 (tris(8-hydroxyquinolinato)aluminum), 1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzoimidazol-1-yl)phenyl)-9,10-dinaphthylanthracene, TPBi(1,3,5-Tri(1-phenyl-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-(4-biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole), NTAZ(4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole), tBu-PBD(2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole), BAlq(Bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-biphenyl-4-olato)aluminum), Bebq2(beryllium bis(benzoquinolin-10-olate)), It may include ADN (9,10-di(naphthalene-2-yl)anthracene), BmPyPhB (1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene), etc. These can be used individually or in combination of two or more.

[0263] The above-described 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).

[0264] The electron transfer region (140) may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or a combination thereof. In one embodiment, the above-described material may be included in the electron injection layer (142).

[0265] The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.

[0266] The alkali metal-containing compound, alkaline earth metal-containing compound, and rare earth metal-containing compound may include oxides, halides (e.g., fluorides, chlorides, bromides, iodides, etc.), tellurides, or combinations thereof of the alkali metal, alkaline earth metal, and rare earth metal, respectively.

[0267] The above alkali metal complex, alkaline earth metal complex, and rare earth metal complex may include a metal ion of the alkali metal, alkaline earth metal, or rare earth metal described above, and a ligand bound to said metal ion. The ligand may include, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or a combination thereof.

[0268] The thickness of the electron transfer region (140) may be about 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å.

[0269] When the electron transfer region (140) includes an electron injection layer (142) and an electron transport layer (144), the thickness of the electron injection layer (142) may be 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 about 10 Å to about 900 Å, about 10 Å to about 500 Å, or about 100 Å to about 400 Å.

[0270] In the above thickness range, electron injection characteristics and electron transport characteristics can be further improved without an excessive increase in driving voltage, and the stability of the electron transport region (140) can be improved.

[0271] Each layer of the electron transfer region (140) can be formed through processes such as vacuum deposition, spin coating, inkjet printing, laser printing, casting, laser thermal transfer.

[0272] The light-emitting element (ED) may further include a capping layer. The light emission efficiency to the outside of the light-emitting element (ED) can be enhanced through the capping layer.

[0273] As illustrated in FIG. 4, a second capping layer (160b) may be formed on the outer surface of the second electrode (150). In some embodiments, a first capping layer (160a) may be formed on the outer surface of the first electrode (110).

[0274] The refractive index of the first capping layer (160a) and / or the second capping layer (160b) may be 1.6 or higher. For example, for light in the wavelength range of 550 nm to 660 nm, the refractive index of the first capping layer (160a) and / or the second capping layer (160b) may be 1.6 or higher, 1.8 or higher, or 2.0 or higher.

[0275] The first capping layer (160a) and the second capping layer (160b) may each be formed as an organic capping layer containing an organic material, an inorganic capping layer containing an inorganic material, or an organic-inorganic composite capping layer containing both organic and inorganic materials.

[0276] The first capping layer (160a) and / or the second capping layer (160b) may each have a single-layer structure or a multi-layer structure comprising multiple materials.

[0277] In some embodiments, the first capping layer (160a) and / or the second capping layer (160b) may comprise a carbocyclic compound, a heterocyclic compound, an amine group-containing compound, a porphine derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, etc. These may be used alone or in combination of two or more.

[0278] According to one embodiment, the first capping layer (160a) and / or the second capping layer (160b) may include the amine group-containing compound.

[0279] Referring to FIG. 5, the light-emitting element (ED) may include a plurality of light-emitting structures (ES1, ES2, ES3). Each of the light-emitting structures (ES1, ES2, ES3) may include a stacked structure of a hole transport region (120), a light-emitting layer (130), and an electron transport region (140) as described with reference to FIG. 1 to 4. According to exemplary embodiments, the light-emitting element (ED) of FIG. 5 may be a light-emitting element with a tandem structure.

[0280] Charge generation layers (CGL1, CGL2) may be disposed between adjacent light-emitting structures (ES1, ES2, ES3). The charge generation layers (CGL1, CGL2) may include a p-type charge generation layer and / or an n-type charge generation layer.

[0281] The p-type charge generation layer may include a compound that can be utilized as a hole transport host, such as NPB. For example, the p-type charge generation layer may include a compound represented by the chemical formula HT described above. The p-type charge generation layer may further include a p-dopant, such as TCNQ.

[0282] The n-type charge generation layer may include a compound that can be utilized as an electron transport host. For example, the n-type charge generation layer may include a compound represented by the chemical formula ET described above. In one embodiment, the n-type charge generation layer may include a phenanthroline-based compound.

[0283] The charge generation layer (CGL1, CGL2) may include a first charge generation layer (CGL1) disposed between a first light-emitting structure (ES1) and a second light-emitting structure (ES2), and a second charge generation layer (CGL2) disposed between a second light-emitting structure (ES2) and a third light-emitting structure (ES3).

[0284] According to exemplary embodiments, a first light-emitting structure (ES1), a first charge-generating layer (CGL1), a second light-emitting structure (ES2), a second charge-generating layer (CGL2), a third light-emitting structure (ES3), and a second electrode (150) may be sequentially stacked from the upper surface of a first electrode (110).

[0285] 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. As a non-limiting example, the first light-emitting structure (ES1), the second light-emitting structure (ES2), and the third light-emitting structure (ES3) each include a red light-emitting layer, a green light-emitting layer, and a blue light-emitting layer, and a white light-emitting structure may be realized through a tandem structure, but is not limited thereto.

[0286] In FIG. 5, a 3-stack tandem structure in which three light-emitting structures are stacked is illustrated as an example, but the tandem structure of the light-emitting element of the present disclosure is not limited to the structure illustrated in FIG. 5. For example, it may be extended to a 2-stack, or a 4-stack, 5-stack, or more structures as described later with reference to FIG. 6.

[0287] Referring to FIG. 6, as described with reference to FIG. 5, a tandem structure in which a light-emitting structure and a charge-generating layer are alternately and repeatedly stacked can be arranged between the first electrode (110) and the second electrode (150).

[0288] According to exemplary embodiments, a first light-emitting structure (ES1) to an m-th light-emitting structure (ESm) may be sequentially stacked from the upper surface of the first electrode (110) with a charge generating layer in between. The charge generating layer may include a first charge generating layer (CGL1) to an m-1 charge generating layer (CGLm-1) sequentially stacked from the upper surface of the first electrode (110).

[0289] As shown in FIG. 6, a first light-emitting structure (ES1), a first charge-generating layer (CGL1), a second light-emitting structure (ES2), a second charge-generating layer (CGL2), ..., an m-1 light-emitting structure (ESm-1), an m-1 charge-generating layer (CGLm-1), an m-1 light-emitting structure (ESm), and a second electrode (150) can be sequentially stacked from the upper surface of the first electrode (110).

[0290] In some embodiments, m is 4, and the intermediate layer (ITL) of the light-emitting element has a 4-stack tandem structure and may include first to fourth light-emitting structures (ES1, ES2, ES3, ES4) and first to third charge-generating layers (CGL1, CGL2, CGL3). The colored light generated from the first to fourth light-emitting structures (ES1, ES2, ES3, ES4) may be the same or different from one another.

[0291] In one embodiment, the first to fourth light-emitting structures (ES1, ES2, ES3, ES4) may include at least one blue light-emitting structure and at least one green light-emitting structure. As a non-limiting example, the first to third light-emitting structures (ES1, ES2, ES3) correspond to blue light-emitting structures, and the fourth light-emitting structure (ES4) corresponds to a green light-emitting structure.

[0292] In some embodiments, m is 5 and the intermediate layer (ITL) of the light-emitting element has a 5-stack tandem structure and may include first to fifth light-emitting structures (ES1, ES2, ES3, ES4, ES5) and first to fourth charge-generating layers (CGL1, CGL2, CGL3, CGL4). The colored light generated from the first to fifth light-emitting structures (ES1, ES2, ES3, ES4, ES5) may be the same or different from one another.

[0293] In one embodiment, the first to fifth light-emitting structures (ES1, ES2, ES3, ES4, ES5) may include at least one blue light-emitting structure and at least one green light-emitting structure. As a non-limiting example, the first to fifth light-emitting structures (ES, ES2, ES3, ES4, ES5) may include three blue light-emitting structures and two green light-emitting structures. For example, the first, third, and fifth light-emitting structures (ES1, ES3, ES5) correspond to blue light-emitting structures, and the second and fourth light-emitting structures (ES2, ES4) correspond to green light-emitting structures.

[0294] Electronic device

[0295] The light-emitting element (ED) described above can be applied to an electronic device and provided as a light-emitting part or light-emitting unit of the electronic device.

[0296] The above electronic device may include a display device, an advertising board, a guide sign, a light source / lighting, a personal computer such as a notebook computer or a desktop computer, a mobile phone, an e-book, an e-dictionary, an e-notebook, various sensors, a diagnostic device, a healthcare device, and various display parts of a means of transportation (automobile, aircraft, ship, train).

[0297] According to exemplary embodiments, the light-emitting element (ED) can be applied to an organic light-emitting diode (OLED) display device or a quantum dot (QD)-OLED display device.

[0298] FIG. 7 is a schematic cross-sectional view showing a display device according to exemplary embodiments.

[0299] Referring to FIG. 7, the display device may include a circuit layer (CL) disposed on a base substrate (200) and light-emitting elements (ED1, ED2, ED3) disposed on the circuit layer (CL).

[0300] The base substrate (200) may be provided as a support substrate or back-plane substrate of an image display device. A glass substrate or a plastic substrate may be used as the base substrate (100).

[0301] In some embodiments, the base substrate (200) may comprise a polymer material having transparency and flexibility. In this case, the base substrate (200) may be employed in a transparent flexible display device. For example, the base substrate (200) may comprise a polymer material such as polyimide, polysiloxane, epoxy resin, acrylic resin, or polyester. In one embodiment, the base substrate (200) may comprise polyimide.

[0302] The circuit layer (CL) may include transistors (TR1, TR2, TR3). The circuit layer (CL) may include wiring layers and insulating layers that form a thin-film transistor array (TFT-Array).

[0303] The circuit layer (CL) may further include a buffer layer (205) formed on the upper surface of the base substrate (200). Moisture penetrating through the base substrate (200) can be blocked by the buffer layer (205), and the diffusion of impurities between the base substrate (200) and the structure formed on the base substrate (200) can be blocked.

[0304] The buffer layer (205) may include, for example, silicon oxide, silicon nitride, or silicon oxynitride. These may be used alone or in combination of two or more. In some embodiments, the buffer layer (205) may have a stacked structure including a silicon oxide film and a silicon nitride film.

[0305] Transistors (TR1, TR2, TR3) may be disposed on the buffer layer (205). The first transistor (TR1), the second transistor (TR2), and the third transistor (TR3) may be electrically connected to the first light-emitting element (ED1), the second light-emitting element (ED2), and the third light-emitting element (ED3), respectively.

[0306] The transistors (TR1, TR2, TR3) may each include an active layer (210), a gate insulating layer (220), and a gate electrode (230).

[0307] The active layer (210) is disposed on the buffer layer (205) and may be arranged repeatedly / regularly for each pixel. The active layer (210) may include a silicon compound such as amorphous silicon or polysilicon. Some regions of the active layer (210) may be doped with a p-type dopant or an n-type dopant and may include a source region, a drain region, and a channel region.

[0308] The active layer (210) may include an oxide semiconductor such as indium-gallium-zinc oxide (IGZO), zinc-tin oxide (ZTO), or ITZO.

[0309] A gate insulating layer (220) is formed on an active layer (210), and a gate electrode (230) may be laminated on the gate insulating layer (220). As shown in FIG. 6, the gate insulating layer (220) may be formed in a pattern shape that partially covers each active layer (210). Alternatively, the gate insulating layer (220) may extend continuously across a plurality of pixels or light-emitting regions and may be commonly included for the first to third transistors (TR1, TR2, TR3).

[0310] The gate electrode (230) can be overlapped in a vertical direction with the channel region of the active layer (210).

[0311] An interlayer insulating layer (240) covering a gate insulating layer (220) and a gate electrode (230) may be formed on the active layer (210). Connecting electrodes (250, 260) that are in contact with or electrically connected to the active layer (210) may be disposed on the interlayer insulating layer (240).

[0312] The connecting electrodes (250, 260) penetrate the interlayer insulating layer (240) and can be connected to the active layer (210). When the gate insulating layer (220) is formed continuously and commonly across a plurality of light-emitting regions, the connecting electrodes (250, 260) can penetrate the gate insulating layer (220) together.

[0313] The connecting electrodes (250, 260) may include a source electrode (250) that is connected to or in contact with the source region of the active layer (210) and a drain electrode (260) that is connected to or in contact with the drain region of the active layer (210).

[0314] The gate insulating layer (220) and the interlayer insulating layer (240) may include silicon oxide, silicon nitride, or silicon oxynitride, and may have a stacked structure including a silicon oxide film and a silicon nitride film.

[0315] The gate electrode (230) and connecting electrodes (250, 260) may include metals such as Ag, Mg, Al, W, Cu, Ni, Cr, Mo, Ti, Pt, Ta, Nd, Sc, alloys thereof, or nitrides thereof.

[0316] The via insulating film (270) can be formed on the interlayer insulating layer (240) to cover the connecting electrodes (250, 260).

[0317] The via insulating film (270) may accommodate a via structure that electrically connects the first electrode (110) and the drain electrode (260). The via insulating film (270) may be provided as a flattening film of the circuit layer (CL). In some embodiments, the via insulating film (270) may comprise an organic material such as polyimide, epoxy resin, acrylic resin, or polyester.

[0318] A light-emitting element (ED1, ED2, ED3) may be disposed on the via insulating layer (270). For example, as described with reference to FIGS. 1 to 4, the light-emitting element (ED1, ED2, ED3) may include a first electrode (110), a hole transport region (120), a light-emitting layer (130), an electron transport region (140), and a second electrode (150) sequentially stacked from the via insulating layer (170).

[0319] The first electrode (110) can be electrically connected to a transistor (TR1, TR2, TR3) or a connecting electrode (250, 260) included in the circuit layer (CL) through the via structure. As shown in FIG. 7, the first electrode (110) can be in contact with or connected to a drain electrode (260) to be provided as a patterned pixel electrode for each light-emitting region or pixel region.

[0320] A pixel defining film (280) can be formed on a via insulating film (270) to define a light-emitting region or a pixel region. For example, a red light-emitting region, a green light-emitting region, and a blue light-emitting region are separated and defined by the pixel defining film (280), and light-emitting elements (ED1, ED2, ED3) can correspond to a red light-emitting element, a green light-emitting element, and a blue light-emitting element, respectively.

[0321] The pixel defining film (280) can partially cover the first electrode (110) of each light-emitting region.

[0322] As illustrated in FIG. 7, the hole transport region (120) and the electron transport region (140) can be formed continuously and commonly on the pixel defining film (280) and the plurality of first electrodes (110). The light-emitting layer (130) can be formed in the form of separate islands for each light-emitting region or pixel region and can be defined by the pixel defining film (280).

[0323] In some embodiments, the light-emitting layer (130) may also be formed continuously and commonly across a plurality of light-emitting regions or pixel regions. In some embodiments, the hole transport region (120), the light-emitting layer (130), and the electron transport region (140) may all be formed separately and selectively for each light-emitting region or pixel region.

[0324] The second electrode (150) may be provided as a common electrode formed continuously across a plurality of light-emitting regions or pixel regions.

[0325] The encapsulation layer (290) is disposed on the pixel defining film (280) and the light-emitting elements (ED1, ED2, ED3) to protect the light-emitting elements (ED1, ED2, ED3) from moisture or oxygen. The encapsulation layer (290) may be formed as a thin film encapsulation (TFE) having a single layer or a multilayer structure.

[0326] The encapsulation layer (290) may comprise an inorganic film comprising silicon nitride (SiNx), silicon oxide (SiOx), indium tin oxide, indium zinc oxide, or any combination thereof; an organic film comprising polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (e.g., polymethyl methacrylate, polyacrylic acid, etc.), an epoxy resin (e.g., AGE (aliphatic glycidyl ether), etc.) or any combination thereof; or a combination of an inorganic film and an organic film.

[0327] The display device may further 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; or an optical layer such as a polarizing layer, a color conversion layer, or a color filter layer.

[0328] In some embodiments, the electronic device may further include a functional layer disposed on a light-emitting element and comprising a sensor layer, a polarizing layer, a color conversion layer, a color filter layer, a window film, or a combination of at least two of these.

[0329] FIG. 8 is a schematic cross-sectional view showing a display device according to exemplary embodiments.

[0330] Referring to FIG. 8, each light-emitting element (ED1, ED2, ED3) may have a tandem structure, for example, a 2-stack tandem structure.

[0331] In some embodiments, the hole transport region (120) and the electron transport region (140) may be formed continuously and commonly included in the intermediate layer of each light-emitting structure. Additionally, a charge generation layer (CGL) may be continuously extended across a plurality of pixels and commonly included in the intermediate layer of each light-emitting structure.

[0332] The first light-emitting element (ED1) may include a first lower light-emitting layer (130-1a) disposed between the hole transport region (120) and the charge generation layer (CGL), and a first upper light-emitting layer (130-1b) disposed between the charge generation layer (CGL) and the electron transport region (140).

[0333] The second light-emitting element (ED2) may include a second lower light-emitting layer (130-2a) disposed between the hole transport region (120) and the charge generation layer (CGL), and a second upper light-emitting layer (130-2b) disposed between the charge generation layer (CGL) and the electron transport region (140).

[0334] The third light-emitting element (ED3) may include a third lower light-emitting layer (130-3a) disposed between the hole transport region (120) and the charge generation layer (CGL), and a third upper light-emitting layer (130-3b) disposed between the charge generation layer (CGL) and the electron transport region (140).

[0335] The lower light-emitting layer and the upper light-emitting layer included in each light-emitting structure can generate light of the same color. In one embodiment, the first lower light-emitting layer (130-1a) and the first upper light-emitting layer (130-1b) included in the first light-emitting element (ED1) may each correspond to a red light-emitting layer. The second lower light-emitting layer (130-2a) and the second upper light-emitting layer (130-2b) included in the second light-emitting element (ED2) may each correspond to a green light-emitting layer. The third lower light-emitting layer (130-3a) and the third upper light-emitting layer (130-3b) included in the third light-emitting element (ED3) may each correspond to a blue light-emitting layer.

[0336] FIG. 9 is a schematic cross-sectional view showing the stacked form of a light-emitting structure in a display device according to exemplary embodiments. For convenience of illustration and explanation, the circuit layer, base substrate, pixel defining film, etc., are omitted in FIG. 9, and the shape of each layer or configuration of the light-emitting structure is briefly illustrated as a rectangle.

[0337] Referring to FIG. 9, at least one of the light-emitting structures (ED1, ED2, ED3) or pixel regions (PA1, PA2, PA3) has a tandem structure including a plurality of light-emitting layers, and at least one may have a single light-emitting layer structure.

[0338] In some embodiments, one of the light-emitting structures (ED1, ED2, ED3) or pixel regions (PA1, PA2, PA3) may have a tandem structure, and the others may have a single light-emitting layer structure.

[0339] As illustrated in FIG. 9, a first pixel area (PA1), a second pixel area (PA2), and a third pixel area (PA3) may each include a first light-emitting element (ED1), a second light-emitting element (ED2), and a third light-emitting element (ED3). In some embodiments, the first pixel area (PA1), the second pixel area (PA2), and the third pixel area (PA3) may correspond to a red pixel area, a green pixel area, and a blue pixel area, respectively.

[0340] The hole transport region (120), electron transport region (140), and second electrode (150) may be provided as a common layer that extends continuously across the first pixel region (PA1), the second pixel region (PA2), and the third pixel region (PA3).

[0341] A first light-emitting element (ED1) included in a first pixel area (PA1) may include a first light-emitting layer (130-1), and a second light-emitting element (ED2) included in a second pixel area (PA2) may include a second light-emitting layer (130-2). The first light-emitting layer (130-1) and the second light-emitting layer (130-2) may each be a single-layer light-emitting layer.

[0342] The third light-emitting element (ED3) included in the third pixel area (PA3) may have, for example, a 2-stack tandem structure. The third light-emitting element (ED3) may include a third lower light-emitting layer (130-3a) and a third upper light-emitting layer (130-3b) separated by a charge generation layer (CGL). The third lower light-emitting layer (130-3a) and the third upper light-emitting layer (130-3b) may each correspond to a blue light-emitting layer.

[0343] A lower electron transfer region (140a) may be disposed between the charge generation layer (CGL) and the third lower light-emitting layer (130-3a). An upper hole transfer region (120b) may be disposed between the charge generation layer (CGL) and the third upper light-emitting layer (130-3b).

[0344] Accordingly, a tandem structure of light-emitting structures in which a first electrode (110), a hole transport region (120), a third lower light-emitting layer (130-3a), a lower electron transport region (140a), a charge generation layer (CGL), an upper hole transport region (120b), a third upper light-emitting layer (130-3b), an electron transport region (140), and a second electrode (150) are sequentially stacked may be disposed in the third pixel region (PA3).

[0345] FIG. 10 is a schematic cross-sectional view showing a display device according to exemplary embodiments.

[0346] FIG. 10 illustrates a display device with a QD-OLED structure according to exemplary embodiments. Detailed descriptions of configurations and structures that are substantially the same or similar as those described with reference to FIG. 7 are omitted.

[0347] Referring to FIG. 10, a pixel defining film (280) and a light-emitting element (ED) may be disposed on the circuit layer (CL) as described with reference to FIG. 6. According to exemplary embodiments, light of the same wavelength range may be emitted for each pixel. In one embodiment, blue light may be emitted from each light-emitting element (ED).

[0348] In some embodiments, a light-emitting element of the tandem structure described with reference to FIG. 5 may be disposed in each light-emitting region. In this case, an intermediate layer (ITL) included in the light-emitting element (ED) may be formed continuously and commonly across a plurality of light-emitting regions.

[0349] A color control layer (CCL) including color control units (CCP1, CCP2, CCP3) may be disposed on the packaging layer (290).

[0350] The color control units (CCP1, CCP2, CCP3) may include a phototransformer such as a quantum dot or a phosphor. The wavelength of light introduced into each color control unit (CCP1, CCP2, CCP3) may be converted and emitted by the phototransformer.

[0351] Color control units (CCP1, CCP2, CCP3) can be separated or spaced apart from each other by a bank (BM). The bank (BM) can substantially overlap with the pixel definition film (280), and the color control units (CCP1, CCP2, CCP3) can substantially overlap with the light-emitting layer (130).

[0352] The color control layer (CCL) may include a first color control unit (CCP1) comprising a first quantum dot that converts a first color light provided by a light-emitting element (ED) into a second color light, a second color control unit (CCP2) comprising a second quantum dot that converts the first color light into a third color light, and a third color control unit (CCP3) that transmits the first color light.

[0353] In some embodiments, the first color light, the second color light, and the third color light may each be blue light, red light, and green light. The first quantum dot and the second quantum dot may each be a red quantum dot and a green quantum dot.

[0354] The color control units (CCP1, CCP2, CCP3) may further include scatterers such as inorganic particles. The third color control unit (CCP3) may not include quantum dots and may include scatterers. The scatterers may include TiO2, ZnO, Al2O3, SiO2, hollow silica, etc. These may be used individually or in combination of two or more.

[0355] The color control units (CCP1, CCP2, CCP3) may further include a binder resin that disperses the quantum dots and scatterers. The binder resin may include acrylic resin, urethane resin, silicone resin, epoxy resin, etc.

[0356] A color filter layer (CFL) including color filters (CF1, CF2) and a light-blocking portion (CP) may be disposed on the color control layer (CCL).

[0357] The color filter layer (CFL) may include a first filter (CF1) that transmits second color light, a second filter (CF2) that transmits third color light, and a third filter that transmits first color 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.

[0358] Color filters (CF1, CF2) may include a photosensitive binder resin and a colorant comprising a pigment and / or dye. The first filter (CF1) may include a red pigment or dye, and the second filter (CF2) may include a green pigment or dye.

[0359] A light-blocking section (CP) may be disposed between the above color filters. In some embodiments, the light-blocking section may include a first light-blocking section (CP1) and a second light-blocking section (CP2) comprising color materials of different colors.

[0360] In some embodiments, the first light-blocking part (CP1) includes a blue color material, and the second light-blocking part (CP2) may include a red color material or a black color material. In one embodiment, in the blue light-emitting region, the portion of the first light-blocking part (CP1) exposed between the second light-blocking parts (CP2) may be provided as a blue color filter, and a separate color filter (third filter) may be omitted.

[0361] A first barrier layer (310) may be disposed between the color control layer (CCL) and the light-emitting element (ED) (or encapsulation layer (290)). A second barrier layer (320) may be disposed between the color control layer (CCL) and the color filter layer (CFL).

[0362] The barrier layer (310, 320) may include at least one inorganic layer. For example, the barrier layer (310, 320) may include silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, silicon oxynitride, etc.

[0363] The barrier layer (310, 320) may have a multilayer structure that further includes an organic layer.

[0364] FIG. 11 is a schematic cross-sectional view showing a display device according to exemplary embodiments. Detailed descriptions of configurations and structures substantially identical or similar to those described with reference to FIG. 10 are omitted.

[0365] Referring to FIG. 11, a light-emitting element (ED) corresponding to color control units (CCP1, CCP2, CCP3) is disposed on a first electrode (110) provided as a pixel electrode, and the light-emitting element (ED) may have a tandem structure.

[0366] In some embodiments, as described with reference to FIG. 5, a first light-emitting structure (ES1), a first charge-generating layer (CGL1), a second light-emitting structure (ES2), a second charge-generating layer (CGL2), and a third light-emitting structure (ES3) may be sequentially stacked between a first electrode (110) and a second electrode (150). 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 formed continuously in a plurality of pixel regions or light-emitting regions.

[0367] In one embodiment, the first light-emitting structure (ES1), the second light-emitting structure (ES2), and the third light-emitting structure (ES3) generate different colored light, and the light-emitting element (ED) can generate white light. In one embodiment, the first light-emitting structure (ES1), the second light-emitting structure (ES2), and the third light-emitting structure (ES3) can all generate blue light.

[0368] In some embodiments, as described with reference to FIG. 6, the light-emitting element (ED) may include a tandem structure with a stack of 4, 5, or more stacks.

[0369] FIG. 12 is a schematic diagram showing an electronic device according to exemplary embodiments.

[0370] According to exemplary embodiments, the electronic device may be implemented in the form of a mobile phone (smartphone), tablet, PC, etc., including the display device described above.

[0371] Referring to FIG. 12, the electronic device may include a window structure (WS), a display panel (DP), and a rear structure (RS).

[0372] The window structure (WS) provides an external display surface perceived by a user, such as the viewing surface of a mobile phone, for example, and may include a transparent material film. For example, the window structure (WS) may include glass (e.g., ultra-thin glass (UTG)), a hard coating film, a plastic film, etc.

[0373] The outer surface of the window structure (WS) may include an active area (AA) and a peripheral area (PA). The active area (AA) may provide a surface on which an image of the display device is substantially displayed and where a user's touch / command is input. The peripheral area (PA) may substantially correspond to the bezel area of ​​the display device.

[0374] The display panel (DP) includes the display device described above and may include a display area (DA) and a non-display area (NDA). The display area (DA) of the display panel (DP) may substantially correspond to or overlap with the active area (AA) of the window structure (WS). The non-display area (NDA) of the display panel (DP) may substantially correspond to or overlap with the peripheral area (PA) of the window structure (WS).

[0375] In some embodiments, functional element regions (E1, E2) may be included within the active region (AA) of the window structure (WS). For example, the first functional element region (E1) may be included at one end of the active region (AA) and may be implemented, for example, in the form of a camera hole. The second functional element region (E2) may be provided as a fingerprint sensing region.

[0376] For example, a sensor structure for touch sensing or fingerprint sensing may be placed within the display panel (DP), or between the window structure (WS) and the display panel (DP).

[0377] The rear structure (RS) may be provided as a chassis structure or housing of the display device or electronic device. A cover panel may be disposed between the rear structure (RS) and the display panel (DP).

[0378] FIG. 13 is a schematic diagram showing an electronic device according to exemplary embodiments.

[0379] The electronic device may be installed, embedded, attached, or integrated into the vehicle (400). The vehicle (400) is not limited to the structure shown in FIG. 13 and may include means of transportation such as a three-wheeled or four-wheeled vehicle, construction machinery, a two-wheeled vehicle, a motor device, a bicycle, a train, etc. Additionally, electric vehicles, hybrid vehicles, etc. may be included in the vehicle (400).

[0380] Referring to FIG. 13, at least one of the first to fifth display devices (DP1, DP2, DP3, DP4, DP5) can be applied to a vehicle (400).

[0381] According to exemplary embodiments, the first display device (DP1) may be placed in the cluster area (410). In the cluster area (410), driving information such as mileage and speed, and various warning lights may be displayed.

[0382] The second display device (DP2) may be placed on the front window (FW) of the vehicle (400). For example, the second display device (DP2) may be installed in the form of a head-up display (HUD).

[0383] A third display device (DP3) may be placed on the center fascia (420) of the vehicle (400). On the center fascia (420), buttons or switches for controlling the operation of a video / music player, air conditioner, heater, etc., may be displayed, and vehicle information may be displayed.

[0384] The fourth display device (DP4) may be applied to the side mirror (430) of the vehicle (400). The side mirror (430) is installed on both sides, inside and / or outside the vehicle, respectively, and the fourth display device (DP4) may be applied to at least one of the side mirrors (430) on both sides.

[0385] The fifth display device (DP5) may be placed on the passenger seat dashboard (440). Information / images identical or different from those displayed on the cluster area (410) and / or the center fascia (420) may be displayed through the passenger seat dashboard (440).

[0386] A display device according to an exemplary embodiment may be applied to various electronic devices. An electronic device according to one embodiment includes the display device described above and may further include a module or device having additional functions other than the display device.

[0387] FIG. 14 is a block diagram of an electronic device according to one embodiment. Referring to FIG. 14, an electronic device (10) according to one embodiment may include a display module (11), a processor (12), a memory (13), and a power module (14).

[0388] The display module (11) may include the display device described above. The display module or the display device may include the light-emitting element described above.

[0389] The processor (12) may include at least one of a central processing unit (CPU), an application processor (AP), a graphic processing unit (GPU), a communication processor (CP), an image signal processor (ISP), and a controller.

[0390] The memory (15) may store data information necessary for the operation of the processor (12) or the display module (11). When the processor (12) executes an application stored in the memory (15), a video data signal and / or an input control signal is transmitted to the display module (11), and the display module (11) can process the received signal and output video information through a display screen.

[0391] The power module (14) may include a power supply module, such as a power adapter or battery device, and a power conversion module that converts the power supplied by the power supply module to generate power necessary for the operation of the electronic device (10).

[0392] At least one of each component of the electronic device (11) described above may be included within the display device according to the embodiments described above. Additionally, some of the individual modules functionally included within a single module may be included within the electronic device, while others may be provided separately from the electronic device. For example, the electronic device may include a display module (11), and the processor (12), memory (13), and power module (14) may be provided in the form of other devices within the electronic device rather than the display device.

[0393] FIG. 15 is a schematic diagram of an electronic device according to various embodiments.

[0394] Referring to FIG. 15, various electronic devices to which a display device according to the embodiments is applied may include not only image display electronic devices such as a smartphone (10_1a), tablet PC (10_1b), laptop (10_1c), TV (10_1d), and desk monitor (10_1e), but also wearable electronic devices including display modules such as smart glasses (10_2a), head-mounted display (10_2b), and smart watch (10_2c), and automotive electronic devices (10_3) including display modules such as a CID (Center Information Display) and room mirror display placed on the instrument panel, center fascia, and dashboard of a car.

[0395] The electronic device may be, for example, a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, a light for indoor or outdoor lighting and / or signaling, a head-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet, a phablet, a personal information terminal (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay, a 3D display, a virtual reality or augmented reality display, a vehicle, a video wall including multiple displays tiled together, a theater or stadium screen, a light therapy device, and a signboard.

[0396] Hereinafter, experimental examples including examples and comparative examples are presented to aid in understanding the present disclosure; however, these examples are merely illustrative of the present disclosure and are not intended to limit the appended claims. It is obvious to those skilled in the art that various changes and modifications to the examples are possible within the scope and spirit of the present disclosure, and that such variations and modifications fall within the scope of the appended claims.

[0398] Example 1: Synthesis of Compound 6

[0399]

[0401] (1) Synthesis of intermediate compound 6-a

[0402] Under an argon atmosphere, [1,1':3',1''-terphenyl]-2'-amine (1 eq), 3-iodo-1,1'-biphenyl (1 eq), Pd2(dba)3 (0.05 eq), tris-tert-butylphosphine (0.1 eq), and sodium tert-butoxide (3 eq) were added to a 1 L flask and dissolved in o-xylene. The reaction solution was then stirred at 140°C for 2 hours. After cooling, water and ethyl acetate were added for extraction to collect the organic layer. The organic layer was then dried with MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure, and the resulting solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain the intermediate compound 6-a (Y: 75%). It was confirmed through ESI-LCMS that the obtained compound was compound 6-a.

[0403] ESI-LCMS: [M] + : C 30 H 23 N. 397.5210.

[0405] (2) Synthesis of intermediate compound 6-b

[0406] Under an argon atmosphere, compound 6-a (1 eq), 1,3-dibromo-5-iodobenzene (2 eq), Pd2(dba)3 (0.05 eq), BINAP (0.1 eq), and sodium tert-butoxide (3 eq) were added to a 1 L flask, dissolved in toluene, and the reaction solution was stirred at 80°C for 6 hours. After cooling, water and ethyl acetate were added for extraction to collect the organic layer, which was then dried with MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure, and the resulting solid was purified and separated by silica gel column chromatography using CH2Cl2 and hexane as developing solvents to obtain the intermediate compound 6-b (Y: 61%). It was confirmed through ESI-LCMS that the obtained compound was compound 6-b.

[0407] ESI-LCMS: [M] + : C 36 H 25 Br2N. 631.4110.

[0409] (3) Synthesis of intermediate compound 6-c

[0410] Intermediate 6-c was synthesized using the same method as for intermediate 6-b, but with 9H-carbazole instead of intermediate 6-a and intermediate 6-b instead of 1,3-dibromo-5-iodobenzene (Yield: 53%). The obtained solid was confirmed to be compound 6-c through ESI-LCMS.

[0411] ESI-LCMS: [M] + : C 48 H 33 BrN2. 717.7100.

[0413] (4) Synthesis of intermediate compound 6-d

[0414] Under an argon atmosphere, intermediate compound 6-c (1 eq), (4,6-bis(phenyl-d5)-1,3,5-triazin-2-yl)boronic acid (1.7 g, 5.9 mmol), potassium carbonate (2 g, 15 mmol), and Pd(PPh3)4 (1 eq) were added to a 2 L flask and dissolved in toluene and ethanol:H2O (5:1:2). The reaction solution was then stirred at 100°C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction to collect the organic layer. The mixture was then dried with MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure, and the resulting solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain intermediate compound 6-d (white solid, 73%).

[0415] ESI-LCMS: [M] + : C 63 H 43 N5. 870.0720.

[0417] (5) Synthesis of Compound 6

[0418] Under an argon atmosphere, compound 6-d (1 eq) was placed in a 500 mL flask and dissolved in o-dichlorobenzene. After cooling with water and ice, BBr3 (5 eq.) was slowly added dropwise, and the reaction solution was stirred at 140°C for 12 hours. After cooling, triethylamine (5 equiv.) was added to terminate the reaction. The organic layer was collected by extraction with water / CH2Cl2, dried with MgSO4, and filtered. The solvent was removed from the filtered solution under reduced pressure, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain compound (yellow solid, 25%). It was confirmed through 1H-NMR and ESI-LCMS that the obtained compound was compound 6.

[0419] ESI-LCMS: [M] + : C 63 H 40 BN5. 877.8580.

[0420] 1 H-NMR (400 MHz, CDCl3): 9.10 (s, 2H), 7.8-7.75 (m, 8H), 7.68-7.50 (m, 14H), 7.47-7.25 (m, 12H), 7.20-7.10 (m, 4H)

[0422] Example 2: Synthesis of Compound 7

[0423]

[0424] (1) Synthesis of intermediate compound 7-a

[0425] Intermediate 7-a was synthesized using 3,6-di-tert-butyl-9H-carbazole instead of intermediate 6-a and intermediate 6-b instead of 1,3-dibromo-5-iodobenzene in the same manner as the synthesis of intermediate 6-b (Yield: 56%). The obtained solid was confirmed to be compound 7-a through ESI-LCMS.

[0426] ESI-LCMS: [M] + : C 56 H 49 BrN2.828.3079.

[0428] (2) Synthesis of intermediate compound 7-b

[0429] Intermediate 7-b was synthesized using intermediate 7-a instead of intermediate 6-c in the same manner as the synthesis of intermediate 6-d (yield: 62%). The obtained solid was confirmed to be compound 7-b through ESI-LCMS.

[0430] ESI-LCMS: [M] + : C 71 H 59 N5. 981.4770.

[0432] (3) Synthesis of Compound 7

[0433] Compound 7 was synthesized using intermediate 7-b instead of intermediate 6-d in the same manner as the synthesis of Compound 6 (yield: 22%). The obtained solid was confirmed to be Compound 7 through ESI-LCMS.

[0434] ESI-LCMS: [M] + : C 71 H 56 BN5. 989.4629.

[0435] 1 H-NMR (400 MHz, CDCl3): 9.02(s, 2H), 7.78-7.70(m, 4H), 7.68-7.62(m,8H), 7.55(m,4H) 7.48-7.32 (m, 16H), 7.21-7.16 (m, 4H), 1.52-1.46(S, 18H)

[0437] Example 3: Synthesis of Compound 46

[0438]

[0439] (1) Synthesis of intermediate compound 46-a

[0440] Intermediate 46-a was synthesized using the same method as for intermediate 6-d, but with 1-bromo-3-iodobenzene instead of intermediate 6-c and (3,5-di-tert-butylphenyl)boronic acid instead of (4,6-bis(phenyl-d5)-1,3,5-triazin-2-yl)boronic acid (yield: 73%). The obtained solid was confirmed to be compound 46-a via ESI-LCMS.

[0441] ESI-LCMS: [M] + : C 20 H 25 Br. 344.1140.

[0443] (2) Synthesis of intermediate compound 46-b

[0444] Intermediate 46-b was synthesized using intermediate 46-a instead of 3-iodo-1,1'-biphenyl in the same manner as the synthesis of intermediate 6-a (yield: 69%). The obtained solid was confirmed to be compound 46-b through ESI-LCMS.

[0445] ESI-LCMS: [M] + : C 38 H 39 N. 509.3083.

[0447] (3) Synthesis of intermediate compound 46-c

[0448] Intermediate 46-c was synthesized using intermediate 46-b instead of intermediate 6-a in the same manner as the synthesis of intermediate 6-b (yield: 53%). The obtained solid was confirmed to be compound 46-c through ESI-LCMS.

[0449] ESI-LCMS: [M] + : C 44 H 41 Br2N. 741.1606.

[0451] (4) Synthesis of intermediate compound 46-d

[0452] Intermediate 46-d was synthesized using the same method as for intermediate 6-b, but with 3,6-di-tert-butyl-9H-carbazole instead of intermediate 6-a and intermediate 46-c instead of 1,3-dibromo-5-iodobenzene (Yield: 52%). The obtained solid was confirmed to be compound 46-d through ESI-LCMS.

[0453] ESI-LCMS: [M] + : C 64 H 65 BrN2. 940.4331.

[0455] (5) Synthesis of intermediate compound 46-e

[0456] Intermediate 46-e was synthesized using intermediate 46-d instead of intermediate 6-c in the same manner as the synthesis of intermediate 6-d (yield: 43%). The obtained solid was confirmed to be compound 46-e through ESI-LCMS.

[0457] ESI-LCMS: [M] + : C 79 H 75 N5. 1093.6022.

[0459] (6) Synthesis of Compound 46

[0460] Compound 46 was synthesized using intermediate 46-e instead of intermediate 6-d in the same manner as the synthesis of compound 6 (yield: 23%). The obtained solid was confirmed to be compound 46 through ESI-LCMS.

[0461] ESI-LCMS: [M] + : C 79 H 72 BN5. 1101.5881.

[0462] 1 H-NMR (400 MHz, CDCl3): 9.03(s, 2H), 7.76-7.70(m, 4H), 7.65-7.58(m,8H), 7.53(m,4H) 7.49-7.35 (m, 14H), 7.22-7.18 (m, 4H), 1.52-1.46(S, 18H), 1.44-1.40(S, 18H)

[0464] Example 4: Synthesis of Compound 50

[0465]

[0466] (1) Synthesis of intermediate compound 50-a

[0467] Intermediate 50-a was synthesized using 1-(tert-butyl)-3-iodobenzene instead of 3-iodo-1,1'-biphenyl in the same manner as the synthesis of intermediate 6-a (yield: 83%). The obtained solid was confirmed to be compound 50-a through ESI-LCMS.

[0468] ESI-LCMS: [M] + : C 28 H 27 N. 377.2143.

[0470] (2) Synthesis of intermediate compound 50-b

[0471] Intermediate 50-b was synthesized using intermediate 50-a instead of intermediate 6-a in the same manner as the synthesis of intermediate 6-b (yield: 55%). The obtained solid was confirmed to be compound 50-b through ESI-LCMS.

[0472] ESI-LCMS: [M] + : C 34 H 29 Br2N. 609.0667.

[0474] (3) Synthesis of intermediate compound 50-c

[0475] Intermediate 50-c was synthesized using intermediate 50-b instead of intermediate 46-c in the same manner as the synthesis of intermediate 46-d (Yield: 55%). The obtained solid was confirmed to be compound 50-c through ESI-LCMS.

[0476] ESI-LCMS: [M] + : C 54 H 53 BrN2. 808.3392.

[0478] (4) Synthesis of intermediate compound 50-d

[0479] Intermediate 50-d was synthesized using intermediate 50-c instead of intermediate 6-c in the same manner as the synthesis of intermediate 6-d (Yield: 43%). The obtained solid was confirmed to be compound 50-d through ESI-LCMS.

[0480] ESI-LCMS: [M] + : C 69 H 63 N5. 961.5083.

[0482] (5) Synthesis of Compound 50

[0483] Compound 50 was synthesized using intermediate 50-d instead of intermediate 6-d in the same manner as the synthesis of Compound 6 (Yield: 19%). The obtained solid was confirmed to be Compound 50 through ESI-LCMS.

[0484] ESI-LCMS: [M] + : C 69 H 60 BN5. 969.4642.

[0485] 1 H-NMR (400 MHz, CDCl3): 9.11(s, 2H), 7.80-7.75(m, 4H), 7.69-7.58(m,6H), 7.55(m,4H) 7.53-7.45 (m, 13H), 7.33-7.28 (m, 4H), 1.80-1.76(S, 9H), 1.52-1.46(S, 18H)

[0487] Example 5: Synthesis of Compound 62

[0488]

[0489] (1) Synthesis of intermediate compound 62-a

[0490] Intermediate 62-a was synthesized using 2-bromodibenzo[b,d]furan instead of 3-iodo-1,1'-biphenyl in the same manner as the synthesis of intermediate 6-a (yield: 71%). The obtained solid was confirmed to be compound 62-a through ESI-LCMS.

[0491] ESI-LCMS: [M] + : C 30 H 21 NO. 411.1623.

[0493] (2) Synthesis of intermediate compound 50-b

[0494] Intermediate 62-b was synthesized using intermediate 62-a instead of intermediate 6-a in the same manner as the synthesis of intermediate 6-b (yield: 53%). The obtained solid was confirmed to be compound 62-b through ESI-LCMS.

[0495] ESI-LCMS: [M] + : C 36 H 23 Br2NO. 643.0146.

[0497] (3) Synthesis of intermediate compound 62-c

[0498] Intermediate 62-c was synthesized using intermediate 62-b instead of intermediate 46-c in the same manner as the synthesis of intermediate 46-d (Yield: 58%). The obtained solid was confirmed to be compound 62-c through ESI-LCMS.

[0499] ESI-LCMS: [M] + : C 56 H 47 BrN2O. 842.2872.

[0501] (4) Synthesis of intermediate compound 62-d

[0502] Intermediate 62-d was synthesized using intermediate 62-c instead of intermediate 6-c in the same manner as the synthesis of intermediate 6-d (yield: 42%). The obtained solid was confirmed to be compound 62-d through ESI-LCMS.

[0503] ESI-LCMS: [M] + : C 71 H 57 N5O. 995.4563.

[0505] (5) Synthesis of Compound 62

[0506] Compound 62 was synthesized using intermediate 62-d instead of intermediate 6-d in the same manner as the synthesis of compound 6 (yield: 19%). The obtained solid was confirmed to be compound 62 through ESI-LCMS.

[0507] ESI-LCMS: [M] + : C 71 H 54 BN5O. 1003.4421.

[0508] 1H-NMR (400 MHz, CDCl3): 9.10(s,1H), 9.02(s,1H), 7.82-7.78(m, 4H), 7.71-7.65(m,8H), 7.60-7.55(m,6H) 7.53-7.46 (m, 12H), 7.40-7.35 (m, 4H) , 1.52-1.46(S, 18H)

[0510] Example 6: Synthesis of Compound 80

[0511]

[0512] (1) Synthesis of intermediate compound 80-a

[0513] Intermediate 80-a was synthesized using 5'-(tert-butyl)-[1,1':3',1''-terphenyl]-2'-amine instead of [1,1':3',1''-terphenyl]-2'-amine in the same manner as the synthesis of intermediate 6-a (yield: 81%). The obtained solid was confirmed to be compound 80-a through ESI-LCMS.

[0514] ESI-LCMS: [M] + : C 34 H 31 N. 453.2457.

[0516] (2) Synthesis of intermediate compound 80-b

[0517] Intermediate 80-b was synthesized using intermediate 80-a instead of intermediate 6-a in the same manner as the synthesis of intermediate 6-b (yield: 60%). The obtained solid was confirmed to be compound 80-b through ESI-LCMS.

[0518] ESI-LCMS: [M] + : C 40 H 33 Br2N. 685.0980.

[0520] (3) Synthesis of intermediate compound 80-c

[0521] Intermediate 80-c was synthesized using intermediate 80-b instead of intermediate 46-c in the same manner as the synthesis of intermediate 46-d (Yield: 62%). The obtained solid was confirmed to be compound 80-c through ESI-LCMS.

[0522] ESI-LCMS: [M] + : C 60 H 57 BrN2. 884.3705.

[0524] (4) Synthesis of intermediate compound 80-d

[0525] Intermediate 80-d was synthesized using intermediate 80-c instead of intermediate 6-c in the same manner as the synthesis of intermediate 6-d (yield: 55%). The obtained solid was confirmed to be compound 80-d through ESI-LCMS.

[0526] ESI-LCMS: [M] + : C 75 H 67 N5. 1037.5396

[0528] (5) Synthesis of Compound 80

[0529] Compound 80 was synthesized using intermediate 80-d instead of intermediate 6-d in the same manner as the synthesis of compound 6 (yield: 22%). The obtained solid was confirmed to be compound 80 through ESI-LCMS.

[0530] ESI-LCMS: [M] + : C 75 H 64 BN5. 1045.5255.

[0531] 1 H-NMR (400 MHz, CDCl3): 9.10 (s, 2H), 7.8-7.75 (m, 8H), 7.68-7.50 (m, 13H), 7.47-7.25 (m, 10H), 7.20-7.10 (m, 4H), 1.51-1.48 (s, 18H), 1.46-1.44(s, 9H)

[0533] Example 7: Synthesis of Compound 88

[0534]

[0535] (1) Synthesis of intermediate compound 88-a

[0536] Intermediate 88-a was synthesized using [1,1':3',1'':3'',1''':3''',1''''-quinquephenyl]-2''-amine instead of [1,1':3',1'':3'',1''''-quinquephenyl]-2''-amine in the same manner as the synthesis of intermediate 6-a (yield: 78%). The obtained solid was confirmed to be compound 88-a through ESI-LCMS.

[0537] ESI-LCMS: [M] + : C 42 H 31 N. 549.2457.

[0539] (2) Synthesis of intermediate compound 88-b

[0540] Intermediate 88-b was synthesized using intermediate 88-a instead of intermediate 6-a in the same manner as the synthesis of intermediate 6-b (yield: 62%). The obtained solid was confirmed to be compound 88-b through ESI-LCMS.

[0541] ESI-LCMS: [M] + : C 48 H 33 Br2N. 781.0980.

[0543] (3) Synthesis of intermediate compound 80-c

[0544] Intermediate 88-c was synthesized using intermediate 88-b instead of intermediate 46-c in the same manner as the synthesis of intermediate 46-d (yield: 58%). The obtained solid was confirmed to be compound 88-c through ESI-LCMS.

[0545] ESI-LCMS: [M] + : C 68 H 57 BrN2. 980.3705.

[0547] (4) Synthesis of intermediate compound 80-d

[0548] Intermediate 88-d was synthesized using intermediate 88-c instead of intermediate 6-c in the same manner as the synthesis of intermediate 6-d (yield: 54%). The obtained solid was confirmed to be compound 88-d through ESI-LCMS.

[0549] ESI-LCMS: [M] + : C 83 H 67 N5. 1133.5396

[0551] (5) Synthesis of Compound 88

[0552] Compound 88 was synthesized using intermediate 88-d instead of intermediate 6-d in the same manner as the synthesis of compound 6 (yield: 19%). The obtained solid was confirmed to be compound 88 through ESI-LCMS.

[0553] ESI-LCMS: [M] + : C 83 H 64 BN5. 1045.5255.

[0554] 1 H-NMR (400 MHz, CDCl3): 9.08(s, 2H), 7.8-7.75(m, 8H), 7.68-7.50(m,14H), 7.47-7.25 (m, 18H), 7.20-7.10 (m, 4H), 1.53-1.49 (s, 18H)

[0556] Comparative Examples 1 to 6

[0557] Compounds represented by the following chemical formulas C1 to C6 were prepared as comparative compounds. Specifically, the comparative compounds applied to each comparative example are listed in Table 1 below.

[0558]

[0560] Manufacturing of light-emitting devices

[0561] 15Ω / cm as an anode 2A glass substrate (Corning product) with a 1200 Å ITO electrode formed on it was cut into pieces measuring 50 mm x 50 mm x 0.7 mm, ultrasonically cleaned with isopropyl alcohol and pure water for 5 minutes each, then cleaned by irradiating with ultraviolet light and exposing to ozone for 30 minutes, and then mounted in a vacuum deposition apparatus.

[0562] On the anode, NPD was deposited to form a hole injection layer with a thickness of 300 Å, then H-1-19 was deposited on the hole injection layer to form a hole transport layer with a thickness of 200 Å, and then CzSi was deposited on the hole transport layer to form an electron blocking layer with a thickness of 100 Å.

[0563] Subsequently, a host mixture of HTH1 and ETH26 mixed in a 1:1 ratio, PS-1, and the dopant compounds listed in Table 1 were co-deposited in a weight ratio of 85:14:1 to form a 200 Å thick emissive layer, and TSPO1 was deposited on top of the emissive layer to form a 200 Å thick hole blocking layer. Subsequently, TPBi was deposited on top of the hole blocking layer to form a 300 Å thick electron transport layer, and then LiF was deposited on top of the electron transport layer to form a 10 Å thick electron injection layer. Afterward, a second electrode with a thickness of 3000 Å was formed using Al to form a LiF / Al electrode. Subsequently, a capping layer with a thickness of 700 Å was formed using P4 on top of the electrode. Each layer was formed by vacuum deposition. The compounds used to fabricate the light-emitting devices of the examples and comparative examples are disclosed below. The following materials were commercially available products that were sublimated and purified for use in device fabrication.

[0564]

[0566] Evaluation example

[0567] The physical properties of the light-emitting elements of the examples and comparative examples were measured by the following method, and the results are listed in Table 1.

[0568] 1) 10mA / cm 2The driving voltage and efficiency at the current density were measured using the V7000 OLED IVL Test System (Polaronix).

[0569] 2) The emission wavelength was measured using FluorEssence software with a HORIBA fluoromax+ spectrometer equipped with a xenon light source and a monochromator.

[0570] 3) 10mA / cm 2 The time from the initial value to 95% brightness degradation when continuously driven at the current density was evaluated by comparing it with Comparative Example 1 as the life ratio.

[0572]

[0574] Referring to Table 1, it was confirmed that the light-emitting device in which the condensed heterocyclic group represented by Formula 1 according to the embodiments of the present disclosure is applied as a dopant compound has superior luminous efficiency and / or lifespan characteristics compared to the comparative examples. That is, the condensed heterocyclic group represented by Formula 1 according to the embodiments of the present disclosure has an aryl group, such as a phenyl group, substituted at the ortho position of a phenyl group directly bonded to a nitrogen atom, thereby relatively increasing the intermolecular distance. Consequently, the possibility of intermolecular interactions that can reduce luminous efficiency, such as the occurrence of intermolecular aggregation, the formation of intermolecular excimers, or the formation of intermolecular exiplexes, is relatively low, resulting in excellent luminous efficiency and high lifespan characteristics.

[0575] The above description is merely an example of applying the principles of the present disclosure, and other configurations may be included without departing from the scope of the present disclosure. Explanation of the symbols

[0576] ED: Light-emitting element 10: Electronic devices 11: Display Module 12: Processor 13: Memory 14: Power Module 10_1a: Smartphone 10_1b: Tablet PC 10_1c: Laptop 10_1d: TV 10_1e: Desk Monitor 10_2a: Smart Glasses 10_2b: Head-mounted display 10_2c: Smartwatch 10_3: Automotive Electronic Devices 110: First electrode 120: Hole transfer region 122: Hole injection layer 124: Precision transport layer 130: Emissive layer 140: Electron transport region 142a: First electron injection layer 142b: Second electron injection layer 144: Electron transport layer 150: Second electrode 160a: First capping layer 160b: Second capping layer 200: Base board 205: Buffer layer 210: Active layer 220: Gate insulation layer 230: Gate electrode 240: Interlayer insulation film 250, 260: Connecting electrodes 270: via insulating film 280: Pixel definition membrane 290: Bag layer 300: Functional layer 310, 320: Barrier layer 400: Vehicle

Claims

Claim 1 Condensed heterocyclic compound represented by the following chemical formula 1: [Chemical Formula 1] (In Chemical Formula 1, R1 to R5 are the same or different from each other and each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, nitro group, substituted or unsubstituted C1-C 60 alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl groups, substituted or unsubstituted C1-C 60 alkoxy groups, substituted or unsubstituted C3-C 60 cycloalkyl groups, substituted or unsubstituted C5-C 60 cycloalkenyl groups of, substituted or unsubstituted C3-C 60 heterocycloalkyl groups, substituted or unsubstituted C3-C 60 heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 aryl groups, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 The aryloxy group of, substituted or unsubstituted C6-C 60 arylthio group of, substituted or unsubstituted C8-C 60 A condensed polycyclic group, -SiRR'R", -P(=O)RR', -NRR', -BRR', -C(=O)R, or -S(=O)2R, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted C3-C 60 cycloalkyl ring, substituted or unsubstituted C5-C 60 cycloalkenyl ring of, substituted or unsubstituted C3-C 60 heterocycloalkyl ring of, substituted or unsubstituted C3-C 60 heterocycloalkenyl ring of, substituted or unsubstituted C6-C 60 aryl ring or substituted or unsubstituted C2-C 60 Forming a heteroaryl ring, Q1 is directly bonded, O, NR, CRR', S, or Se, and R, R', and R" are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, substituted or unsubstituted C1-C 60 alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl groups, substituted or unsubstituted C1-C 60 alkoxy groups, substituted or unsubstituted C3-C 60 cycloalkyl groups, substituted or unsubstituted C5-C 60 cycloalkenyl groups of, substituted or unsubstituted C3-C 60 heterocycloalkyl groups, substituted or unsubstituted C3-C 60 heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 aryl groups, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 The aryloxy group of, substituted or unsubstituted C6-C 60 arylthio group or substituted or unsubstituted C8-C 60 A condensation polycyclic group, r1 is an integer from 0 to 5, r2 is an integer from 0 to 4, r3 is an integer from 0 to 2, r4 is an integer from 0 to 6, r5 is an integer from 0 to 7, and if r1 to r5 are each 2 or more, multiple R1 to R5 are each independently identical or different from each other). Claim 2 Claim 1, wherein Chemical Formula 1 is a condensed heterocyclic compound represented by the following Chemical Formula 1-1: [Chemical Formula 1-1] (In Chemical Formula 1-1, R1, R3 to R5, Q1, r1, and r3 to r5 are the same as defined in Chemical Formula 1, and R6 and R7 are the same or different from each other, and each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, nitro group, substituted or unsubstituted C1-C 60 alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl groups, substituted or unsubstituted C1-C 60 alkoxy groups, substituted or unsubstituted C3-C 60 cycloalkyl groups, substituted or unsubstituted C5-C 60 cycloalkenyl groups of, substituted or unsubstituted C3-C 60 heterocycloalkyl groups, substituted or unsubstituted C3-C 60 heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 aryl groups, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 The aryloxy group of, substituted or unsubstituted C6-C 60 arylthio group of, substituted or unsubstituted C8-C 60 A condensed polycyclic group, -SiRR'R", -P(=O)RR', -NRR', -BRR', -C(=O)R, or -S(=O)2R, wherein two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C3-C 60 cycloalkyl ring, substituted or unsubstituted C5-C 60 cycloalkenyl ring of, substituted or unsubstituted C3-C 60 heterocycloalkyl ring of, substituted or unsubstituted C3-C 60 heterocycloalkenyl ring of, substituted or unsubstituted C6-C 60 aryl ring or substituted or unsubstituted C2-C 60 Forming a heteroaryl ring, R, R', and R" are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, substituted or unsubstituted C1-C 60 alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl groups, substituted or unsubstituted C1-C 60 alkoxy groups, substituted or unsubstituted C3-C 60 cycloalkyl groups, substituted or unsubstituted C5-C 60 cycloalkenyl groups of, substituted or unsubstituted C3-C 60 heterocycloalkyl groups, substituted or unsubstituted C3-C 60 heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 aryl groups, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 The aryloxy group of, substituted or unsubstituted C6-C 60 arylthio group or substituted or unsubstituted C8-C 60 It is a condensed polycyclic group, r6 is an integer from 0 to 3 and r7 is an integer from 0 to 5, and if r6 and r7 are each 2 or more, multiple R6s and R7 are each independently identical or different from each other). Claim 3 Claim 1, wherein Chemical Formula 1 is a condensed heterocyclic compound represented by any one of the following Chemical Formulas 2-1 to 2-4: [Chemical Formula 2-1] [Chemical Formula 2-2] [Chemical Formula 2-3] [Chemical Formula 2-4] (In Chemical Formulas 2-1 to 2-4, R1 to R5 and r1 to r5 are the same as defined in Chemical Formula 1, and R8 is hydrogen, deuterium, halogen, hydroxyl group, cyano group, nitro group, substituted or unsubstituted C1-C 60 alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl groups, substituted or unsubstituted C1-C 60 alkoxy groups, substituted or unsubstituted C3-C 60 cycloalkyl groups, substituted or unsubstituted C5-C 60 cycloalkenyl groups of, substituted or unsubstituted C3-C 60 heterocycloalkyl groups, substituted or unsubstituted C3-C 60 heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 aryl groups, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 The aryloxy group of, substituted or unsubstituted C6-C 60 arylthio group of, substituted or unsubstituted C8-C 60 A condensed polycyclic group, -SiRR'R", -P(=O)RR', -NRR', -BRR', -C(=O)R, or -S(=O)2R, wherein two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C3-C 60 cycloalkyl ring, substituted or unsubstituted C5-C 60 cycloalkenyl ring of, substituted or unsubstituted C3-C 60 heterocycloalkyl ring of, substituted or unsubstituted C3-C 60 heterocycloalkenyl ring of, substituted or unsubstituted C6-C 60 aryl ring or substituted or unsubstituted C2-C 60 Forming a heteroaryl ring, R, R', and R" are each independently hydrogen, deuterium, halogen, hydroxyl group, cyano group, substituted or unsubstituted C1-C 60 alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl groups, substituted or unsubstituted C1-C 60 alkoxy groups, substituted or unsubstituted C3-C 60 cycloalkyl groups, substituted or unsubstituted C5-C 60 cycloalkenyl groups of, substituted or unsubstituted C3-C 60 heterocycloalkyl groups, substituted or unsubstituted C3-C 60 heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 aryl groups, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 The aryloxy group of, substituted or unsubstituted C6-C 60 arylthio group or substituted or unsubstituted C8-C 60 It is a condensed polycyclic group, R8 is an integer from 0 to 7, and if R8 is 2 or more, multiple R8s are each independently identical or different from each other). Claim 4 In claim 1, R1 is hydrogen, deuterium, or substituted or unsubstituted C6-C 60 aryl group of, condensed heterocyclic compound. Claim 5 In claim 1, R2 is hydrogen, deuterium, substituted or unsubstituted C1-C 60 alkyl groups or substituted or unsubstituted C6-C 60 aryl group of, condensed heterocyclic compound. Claim 6 In claim 1, R3 is hydrogen, deuterium, cyano group, substituted or unsubstituted C1-C 60 alkyl groups, substituted or unsubstituted C6-C 60 aryl groups, substituted or unsubstituted C2-C 60 heteroaryl groups, substituted or unsubstituted C6-C 60 The aryloxy group is -SiRR'R" or -NRR', where R, R', and R" are each independently hydrogen, deuterium, substituted or unsubstituted C1-C 60 alkyl groups or substituted or unsubstituted C6-C 60 aryl group of, condensed heterocyclic compound. Claim 7 In claim 1, R4 is hydrogen, deuterium, substituted or unsubstituted C1-C 60 alkyl groups, substituted or unsubstituted C6-C 60 aryl groups or substituted or unsubstituted C2-C 60 It is a heteroaryl group, or a C2-C in which two or more adjacent R4s are bonded to each other, resulting in substitution or non-substitution. 60 Condensed heterocyclic compounds forming a heteroaryl ring. Claim 8 In claim 1, R5 is hydrogen, deuterium, substituted or unsubstituted C1-C 60 alkyl groups, substituted or unsubstituted C6-C 60 aryl groups or substituted or unsubstituted C2-C 60 Condensed heterocyclic compound with a heteroaryl group. Claim 9 A condensed heterocyclic compound according to claim 1, wherein R4 and R5 are each independently hydrogen, deuterium, a substituted or unsubstituted butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted carbazole group, or two or more adjacent groups are combined to form a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzoselenophenyl group. Claim 10 Claim 1, wherein the chemical formula 1 is a condensed heterocyclic compound, which is any one of the following compounds: . Claim 11 A light-emitting device comprising: a first electrode; a second electrode; and an intermediate layer disposed between the first electrode and the second electrode, the intermediate layer comprising a light-emitting layer comprising a condensed heterocyclic compound represented by Formula 1 according to Claim 1. Claim 12 A light-emitting device according to claim 11, wherein the light-emitting layer comprises a host and a dopant, and the condensed heterocyclic compound is provided as a Thermally Activated Delayed Fluorescence (TADF) dopant. Claim 13 A light-emitting element according to claim 12, wherein the dopant further comprises a phosphorescent dopant. Claim 14 A light-emitting device according to claim 11, wherein the light-emitting layer emits green light, and the maximum emission wavelength of the green light is 515 nm to 530 nm. Claim 15 An electronic device comprising a light-emitting element according to claim 11. Claim 16 An electronic device according to claim 15, comprising a display module including the light-emitting element, a processor, a memory, and a power module. Claim 17 An electronic device according to claim 16, wherein the processor comprises at least one selected from the group consisting of a central processing unit (CPU), an application processor (AP), a graphic processing unit (GPU), a communication processor (CP), an image signal processor (ISP), and a controller. Claim 18 The electronic device of claim 15, wherein the electronic device is one of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, an advertising board, an indoor or outdoor lighting and / or signal light, a head-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet, a phablet, a personal information terminal (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay, a 3D display, a virtual reality or augmented reality display, a vehicle, a video wall comprising multiple displays tiled together, a theater or stadium screen, a light therapy device, and a signboard.

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