Light-emitting device, electronic apparatus, electronic device, and heterocyclic compound
By introducing heterocyclic compounds as the host or dopant in the light-emitting device, the charge transport layer structure is optimized, overcoming the limitations of triplet energy levels and luminous efficiency in the prior art, and achieving high-efficiency light emission under low driving voltage.
Patent Information
- Application Number
- CN202510310269.8
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2024-03-21
- Filing Date
- 2025-03-17
- Publication Date
- 2025-09-23
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Figure CN120693047A_ABST
Abstract
Description
[0001] CROSS-REFERENCE TO RELATED APPLICATIONS
[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2024-0039254, filed on March 21, 2024, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field
[0003] Embodiments include a light-emitting device including a heterocyclic compound, electronic equipment and electronic devices including the light-emitting device, and the heterocyclic compound. Background Art
[0004] The light emitting device is a self-emitting device having a wide viewing angle, high contrast, short response time, and excellent characteristics in terms of brightness, driving voltage, and response speed.
[0005] In the light emitting device, a first electrode may be disposed on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode may be sequentially disposed on the first electrode.
[0006] Holes provided by the first electrode migrate toward the emissive layer through the hole transport region, and electrons provided by the second electrode migrate toward the emissive layer through the electron transport region. Carriers such as holes and electrons recombine in the emissive layer to produce excitons. Excitons can transition from an excited state to a ground state, generating light.
[0007] It should be understood that this background section is intended, in part, to provide useful background for understanding the technology. However, this background section may also include concepts, ideas, or cognitions that were not known or understood by those skilled in the relevant art before the corresponding effective filing date of the subject matter disclosed herein. Summary of the Invention
[0008] Embodiments include a light-emitting device including a heterocyclic compound, electronic equipment and electronic devices including the light-emitting device, and the heterocyclic compound.
[0009] Additional aspects will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of embodiments of the disclosure.
[0010] According to an embodiment, a light emitting device may include:
[0011] the first electrode,
[0012] a second electrode facing the first electrode,
[0013] an intermediate layer between the first electrode and the second electrode and including an emission layer, and
[0014] Heterocyclic compound represented by Formula 1:
[0015] [Formula 1]
[0016]
[0017] [Formula 2]
[0018]
[0019] In Equation 1 and Equation 2,
[0020] b1, b6 and b7 can each independently be an integer from 0 to 3,
[0021] b5 can be an integer from 0 to 4,
[0022] Ar1, R1, R 21 to R 24 、R 31 to R 34 and R 41 to R 44 Each of them may be independently a group represented by Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted by at least one R 10a Substituted C6-C 60 Aryloxy groups, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Arylthio group, unsubstituted or substituted with at least one R 10a Substituted C7-C 60 Arylalkyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60heteroarylalkyl group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(═O)(Q1), -S(═O)2(Q1), or -P(═O)(Q1)(Q2),
[0023] R 31 to R 34 and R 41 to R 44 At least one of them may be each independently a group represented by Formula 2,
[0024] Ar2, Ar3 and R5 to R7 can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted by at least one R 10a Substituted C6-C 60 Aryloxy groups, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Arylthio group, unsubstituted or substituted with at least one R 10a Substituted C7-C 60 Arylalkyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 heteroarylalkyl group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(═O)(Q1), -S(═O)2(Q1), or -P(═O)(Q1)(Q2),
[0025] R1, R 21 to R 24 、R 31 to R 34 、R 41 to R 44and two or more of R5 to R7 may be optionally bonded together to form an unsubstituted or substituted group. 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups,
[0026] L1 to L3 may each independently be a single bond, unsubstituted or replaced by at least one R 10a Substituted divalent C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted divalent C1-C 60 Heterocyclic groups,
[0027] a1 to a3 may each independently be an integer from 1 to 5,
[0028] R 10a It can be:
[0029] deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, or a nitro group;
[0030] Each unsubstituted or deuterated, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, C2-C 60 Heteroarylalkyl group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 ),-C(=O)(Q 11 )、-S(=O)2(Q 11 ),-P(=O)(Q 11 )(Q 12 ) or any combination thereof substituted C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group or C1-C 60 alkoxy groups;
[0031] Each unsubstituted or deuterated, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group, C1-C 60 Alkoxy groups, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, C2-C 60 Heteroarylalkyl group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 ),-C(=O)(Q 21 )、-S(=O)2(Q 21 ),-P(=O)(Q 21 )(Q 22 ) or any combination thereof substituted C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group or C2-C 60 a heteroarylalkyl group; or
[0032] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 ),-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 );
[0033] Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 Can each independently be:
[0034] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group or C1-C 60 an alkoxy group; or
[0035] Each unsubstituted or deuterated, -F, cyano group, C1-C 60 Alkyl groups, C1-C 60 C3-C substituted by an alkoxy group, a phenyl group, a biphenyl group or any combination thereof 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C7-C 60 Arylalkyl group or C2-C 60 heteroarylalkyl groups, and
[0036] * indicates the binding site with the adjacent atom.
[0037] In an embodiment, the emission layer may include the heterocyclic compound.
[0038] In embodiments, the emission layer may include a host and a dopant, and the host may include the heterocyclic compound.
[0039] In an embodiment, the light emitting device may have a triplet energy level greater than or equal to about 2.75 eV.
[0040] In an embodiment, the light emitting device may further include at least one of a first capping layer outside the first electrode and a second capping layer outside the second electrode, wherein at least one of the first capping layer and the second capping layer may include the heterocyclic compound.
[0041] According to the embodiment, an electronic device may include the light emitting device.
[0042] In an embodiment, the electronic device may further include a thin film transistor, wherein the thin film transistor may include a source electrode and a drain electrode, and the first electrode of the light emitting device may be electrically connected to at least one of the source electrode and the drain electrode. In an embodiment, the electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarization layer, or any combination thereof.
[0043] According to the embodiment, electronic equipment may include the light emitting device.
[0044] In an embodiment, the electronic device can be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a 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 computer, a tablet phone, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall with multiple displays stitched together, a theater screen, a stadium screen, a light therapy device, or a sign.
[0045] According to an embodiment, the heterocyclic compound may be represented by Formula 1 explained herein.
[0046] In an embodiment, L1 to L3 may each independently be:
[0047] a single key; or
[0048] Each is unsubstituted or substituted with at least one R 10a Substituted phenyl group, naphthalene group, anthracene group, phenanthrene group, triphenylene group, pyrene group, group, cyclopentadiene group, 1,2,3,4-tetrahydronaphthalene group, thiophene group, furan group, indole group, benzoborole group, benzophosphole group, indene group, benzothiophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzoborole group, dibenzophosphole group, fluorene group, dibenzothiophene group, dibenzogermanol group, dibenzothiophene ... Thiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azaindole group, azabenzoborole group, azabenzophosphole group, azaindene group, azabenzothiorrole group, azabenzogermanol group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azadibenzo borocyclopentadiene group, azadibenzophosphole group, azafluorene group, azadibenzosilole group, azadibenzogermanylcyclopentadiene group, azadibenzothiophene group, azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrrole group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzothiazole group, benzooxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group or 5,6,7,8-tetrahydroquinoline group, wherein R 10a Same as defined in Formula 1 and Formula 2.
[0049] In the embodiment, L1 to L3 may each independently be: a single bond; or a group represented by one of Formula 3-1 to Formula 3-28 explained in the specification.
[0050] In an embodiment, a1 to a3 may each independently be an integer from 1 to 3.
[0051] In an embodiment, Ar1, R1, R 21 to R 24 、R 31 to R 34 and R 41 to R 44 Can each independently be:
[0052] The group represented by Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 20 Alkyl group or C1-C 20 alkoxy groups;
[0053] Each is deuterated, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, C1-C 10 C1-C12 substituted with an alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group, a pyrimidinyl group, or any combination thereof 20 Alkyl group or C1-C 20 alkoxy groups;
[0054] Each unsubstituted or deuterated, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, C1-C 10 Alkylphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, yl group, pyrrolyl group, thienyl group, furyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolyl group, isoquinolyl group, benzoquinolyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazole group, a benzothiophene group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophene group, a benzocarbazolyl group, a dibenzothioyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidinyl group, -O(Q 31 )、-S(Q 31 )、-Si(Q31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 ),-P(Q 31 )(Q 32 ),-C(=O)(Q 31 )、-S(=O)2(Q 31 ),-P(=O)(Q 31 )(Q 32 ) or any combination thereof substituted cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, C1-C 10 Alkylphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, yl group, pyrrolyl group, thienyl group, furyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolyl group, isoquinolyl group, benzoquinolyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, a benzothiophenyl group, a benzothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzothiorolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, or an azadibenzothiorolyl group; or
[0055] -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2), and
[0056] Q1 to Q3 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl group; cyano group; nitro group; C1-C 60 Alkyl group; C2-C 60Alkenyl group; C2-C 60 Alkynyl group; C1-C 60 Alkoxy group; or each unsubstituted or deuterated, -F, cyano group, C1-C 60 Alkyl groups, C1-C 60 C3-C substituted by an alkoxy group, a phenyl group, a biphenyl group or any combination thereof 60 Carbocyclic group or C1-C 60 Heterocyclic group.
[0057] In an embodiment, Ar2, Ar3 and R5 to R7 may each independently be:
[0058] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 20 Alkyl group or C1-C 20 alkoxy groups;
[0059] Each is deuterated, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, C1-C 10 C1-C12 substituted with an alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group, a pyrimidinyl group, or any combination thereof 20 Alkyl group or C1-C 20 alkoxy groups;
[0060] Each unsubstituted or deuterated, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, C1-C 10 Alkylphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, yl group, pyrrolyl group, thienyl group, furyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolyl group, isoquinolyl group, benzoquinolyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazole group, a benzothiophene group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophene group, a benzocarbazolyl group, a dibenzothioyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidinyl group, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 ),-P(Q 31 )(Q 32 ),-C(=O)(Q 31 )、-S(=O)2(Q 31 ),-P(=O)(Q 31 )(Q 32 ) or any combination thereof substituted cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, C1-C 10 Alkylphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, yl group, pyrrolyl group, thienyl group, furyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolyl group, isoquinolyl group, benzoquinolyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, a benzothiophenyl group, a benzothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzothiorolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, or an azadibenzothiorolyl group; or
[0061] -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2), and
[0062] Q1 to Q3 and Q 31 To Q 33 Each is independently: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; C1-C 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 Alkynyl group; C1-C 60 Alkoxy group; or each unsubstituted or deuterated, -F, cyano group, C1-C 60 Alkyl groups, C1-C 60 C3-C substituted by an alkoxy group, a phenyl group, a biphenyl group or any combination thereof 60 Carbocyclic group or C1-C 60 Heterocyclic group.
[0063] In an embodiment, R 32 to R 34 and R 42 to R 44 At least one of them may each independently be a group represented by Formula 2.
[0064] In an embodiment, R 41 to R 44 At least one of them may be each independently a group represented by Formula 2, and R 31 to R 34can each independently be hydrogen or deuterium.
[0065] In an embodiment, the heterocyclic compound may be represented by one of Formula 1-1 to Formula 1-4 explained in the specification.
[0066] In the embodiment, the heterocyclic compound may be one of Compound 1 to Compound 70 explained in the specification.
[0067] It will be understood that the above embodiments have been described in a generic and explanatory sense only and not for purposes of limitation, and that the present disclosure is not limited to the above described embodiments. BRIEF DESCRIPTION OF THE DRAWINGS
[0068] The accompanying drawings are included to provide a further understanding of the embodiments and are incorporated into and constitute a part of this specification. The accompanying drawings illustrate embodiments of the present disclosure and its principles. The above and other aspects and features of the present disclosure will become more apparent by describing in detail embodiments of the present disclosure with reference to the accompanying drawings, in which:
[0069] Figure 1 is a schematic cross-sectional view of a light emitting device according to the embodiment;
[0070] Figure 2 is a schematic cross-sectional view of an electronic device according to an embodiment;
[0071] Figure 3 is a schematic cross-sectional view of an electronic device according to another embodiment;
[0072] Figure 4 is a schematic perspective view of an electronic device including a light emitting device according to an embodiment;
[0073] Figure 5 is a schematic perspective view of the exterior of a vehicle as an electronic appliance including a light emitting device according to the embodiment; and
[0074] Figures 6A to 6C Each is a schematic diagram of the interior of a vehicle according to an embodiment. DETAILED DESCRIPTION
[0075] The present disclosure will now be described more fully below with reference to the accompanying drawings in which embodiments are shown. However, the present disclosure may be implemented in different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that the present disclosure will be thorough and complete and will fully convey the scope of the present disclosure to those skilled in the art.
[0076] In the drawings, for convenience of description and for clarity, the size, thickness, ratio and dimensions of elements may be exaggerated. The same reference numerals and / or the same reference characters refer to the same elements throughout.
[0077] In the description, it should be understood that when an element (or region, layer, component, etc.) is referred to as being "on," "connected to," or "coupled to" another element, it can be directly on, directly connected to, or directly coupled to the other element, or one or more intervening elements may be present therebetween. In a similar sense, when an element (or region, layer, component, etc.) is described as "overlying" another element, it can directly overly the other element, or one or more intervening elements may be present therebetween.
[0078] In the description, when an element is “directly on,” “directly connected to,” or “directly coupled to” another element, there are no intervening elements present. For example, “directly on” may mean that two layers or two elements are disposed without additional elements, such as adhesive elements, in between.
[0079] As used herein, articles used in the singular such as "a," "an" and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise.
[0080] As used herein, the term "and / or" includes any and all combinations of one or more than one of the associated listed items. For example, "A and / or B" can be understood to mean "A, B, or A and B." The terms "and" and "or" can be used in conjunction or disjunctive conjunction sense and can be understood as equivalent to "and / or."
[0081] Throughout the specification and claims, for purposes of its meaning and interpretation, the term "at least one of" is intended to include the meaning of "at least one selected from the group consisting of." For example, "at least one of A, B, and C" may be understood to mean only A, only B, only C, or any combination of two or more of A, B, and C, such as ABC, ACC, BC, or CC. When preceding a list of elements, the term "at least one of" modifies the entire list and does not modify the individual elements of the list.
[0082] It should be understood that although the terms first, second, etc. can be used to describe various elements in this article, these elements should not be limited by these terms. These terms are only used to distinguish one element from another element. Therefore, without departing from the teaching of the present disclosure, the first element can be referred to as the second element. Similarly, without departing from the scope of the present disclosure, the second element can be referred to as the first element.
[0083] For ease of description, spatially relative terms "below," "under," "down," "above," "upper," etc. may be used herein to describe the relationship between one element or component and another element or component as illustrated in the accompanying drawings. It should be understood that in addition to the orientation depicted in the accompanying drawings, spatially relative terms are also intended to cover different orientations of the device when in use or operation. For example, in a case where the device illustrated in the accompanying drawings is turned over, a device that is located "below" or "beneath" another device can be placed "above" the other device. Thus, the exemplary term "below" can include both a lower position and an upper position. The device may also be oriented in other directions, and thus the spatially relative terms can be interpreted differently depending on the orientation.
[0084] As used herein, the term "about" or "approximately" includes the stated value and means within an acceptable range of deviation from the stated value as determined by one of ordinary skill in the art taking into account the relevant measurements and errors associated with the measurement of the quantity (e.g., the limitations of the measurement system). For example, "about" can mean within one or more than one standard deviation, or within ±20%, ±10%, or ±5% of the stated value.
[0085] It should be understood that the terms “comprises,” “comprising,” “includes,” “including,” “have,” “having,” “contains,” “containing,” etc. are intended to specify the presence of specified features, integers, steps, operations, elements, components, or combinations thereof in the present disclosure, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.
[0086] Unless otherwise defined or implied herein, all terms (including technical and scientific terms) used have the same meaning as commonly understood by those skilled in the art to which the present disclosure belongs. It should be further understood that terms (such as those defined in commonly used dictionaries) should be interpreted as having a meaning consistent with their meaning in the context of the relevant art and should not be interpreted in an idealized or overly formal sense unless explicitly defined in the specification.
[0087] According to the embodiment, a light emitting device (eg, an organic light emitting device) may include: a first electrode; a second electrode facing the first electrode; an intermediate layer between the first and second electrodes and including an emission layer; and a heterocyclic compound represented by Formula 1.
[0088] Hereinafter, the heterocyclic compound represented by Formula 1 will be described in detail:
[0089] [Formula 1]
[0090]
[0091] [Formula 2]
[0092]
[0093] In Equation 1 and Equation 2,
[0094] b1, b6 and b7 can each independently be an integer from 0 to 3,
[0095] b5 can be an integer from 0 to 4,
[0096] Ar1, R1, R 21 to R 24 、R 31 to R 34 and R 41 to R 44 Each of them may be independently a group represented by Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted by at least one R 10a Substituted C6-C 60 Aryloxy groups, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Arylthio group, unsubstituted or substituted with at least one R 10a Substituted C7-C 60Arylalkyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 heteroarylalkyl group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(═O)(Q1), -S(═O)2(Q1), or -P(═O)(Q1)(Q2),
[0097] R 31 to R 34 and R 41 to R 44 At least one of them may be each independently a group represented by Formula 2,
[0098] Ar2, Ar3 and R5 to R7 can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted by at least one R 10a Substituted C6-C 60 Aryloxy groups, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Arylthio group, unsubstituted or substituted with at least one R 10a Substituted C7-C 60 Arylalkyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 heteroarylalkyl group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(═O)(Q1), -S(═O)2(Q1), or -P(═O)(Q1)(Q2),
[0099] R1, R 21 to R 24 、R 31 to R 34 、R 41to R 44 and two or more of R5 to R7 may be optionally bonded together to form an unsubstituted or substituted group. 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups,
[0100] L1 to L3 may each independently be a single bond, unsubstituted or replaced by at least one R 10a Substituted divalent C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted divalent C1-C 60 Heterocyclic groups,
[0101] a1 to a3 may each independently be an integer from 1 to 5,
[0102] R 10a It can be:
[0103] deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, or a nitro group;
[0104] Each unsubstituted or deuterated, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, C2-C 60 Heteroarylalkyl group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 ),-C(=O)(Q 11 )、-S(=O)2(Q 11 ),-P(=O)(Q 11 )(Q 12 ) or any combination thereof substituted C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group or C1-C 60 alkoxy groups;
[0105] Each unsubstituted or deuterated, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group, C1-C 60 Alkoxy groups, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, C2-C 60 Heteroarylalkyl group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 ),-C(=O)(Q 21 )、-S(=O)2(Q 21 ),-P(=O)(Q 21 )(Q 22 ) or any combination thereof substituted C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group or C2-C 60 a heteroarylalkyl group; or
[0106] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 ),-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ),
[0107] Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 Can each independently be:
[0108] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group or C1-C 60 an alkoxy group; or
[0109] Each unsubstituted or deuterated, -F, cyano group, C1-C 60 Alkyl groups, C1-C 60 C3-C substituted by an alkoxy group, a phenyl group, a biphenyl group or any combination thereof 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C7-C 60 Arylalkyl group or C2-C 60 heteroarylalkyl groups, and
[0110] * indicates the binding site with the adjacent atom.
[0111] In an embodiment, L1 to L3 may each independently be:
[0112] a single key; or
[0113] Each is unsubstituted or substituted with at least one R 10a Substituted phenyl group, naphthalene group, anthracene group, phenanthrene group, triphenylene group, pyrene group, group, cyclopentadiene group, 1,2,3,4-tetrahydronaphthalene group, thiophene group, furan group, indole group, benzoborole group, benzophosphole group, indene group, benzothiophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzoborole group, dibenzophosphole group, fluorene group, dibenzothiophene group, dibenzogermanol group, dibenzothiophene ... Thiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azaindole group, azabenzoborole group, azabenzophosphole group, azaindene group, azabenzothiorrole group, azabenzogermanol group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azadibenzo borocyclopentadiene group, azadibenzophosphole group, azafluorene group, azadibenzosilole group, azadibenzogermanylcyclopentadiene group, azadibenzothiophene group, azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrrole group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzothiazole group, benzooxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group or 5,6,7,8-tetrahydroquinoline group, wherein R 10a Can be the same as described herein.
[0114] In an embodiment, L1 to L3 may each independently be:
[0115] a single key; or
[0116] A group represented by one of Formula 3-1 to Formula 3-28:
[0117]
[0118]
[0119] In formula 3-1 to formula 3-28,
[0120] R 10a can be the same as described in this article,
[0121] c1 can be 0 or 1,
[0122] c2 can be an integer from 0 to 2,
[0123] c3 can be an integer from 0 to 3,
[0124] c4 can be an integer from 0 to 4,
[0125] c6 can be an integer from 0 to 6, and
[0126] * and *' each represent a binding site with an adjacent atom.
[0127] In an embodiment, a1 to a3 may each independently be an integer from 1 to 3.
[0128] In an embodiment, Ar1, R1, R 21 to R 24 、R 31 to R 34 and R 41 to R 44 Can each independently be:
[0129] The group represented by Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 20 Alkyl group or C1-C 20 alkoxy groups;
[0130] Each is deuterated, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, C1-C 10 C1-C12 substituted with an alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group, a pyrimidinyl group, or any combination thereof 20 Alkyl group or C1-C 20 alkoxy groups;
[0131] Each unsubstituted or deuterated, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, C1-C10 Alkylphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, yl group, pyrrolyl group, thienyl group, furyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolyl group, isoquinolyl group, benzoquinolyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazole group, a benzothiophene group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophene group, a benzocarbazolyl group, a dibenzothioyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidinyl group, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 ),-P(Q 31 )(Q 32 ),-C(=O)(Q 31 )、-S(=O)2(Q 31 ),-P(=O)(Q 31 )(Q 32 ) or any combination thereof substituted cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, C1-C 10 Alkylphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, yl group, pyrrolyl group, thienyl group, furyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolyl group, isoquinolyl group, benzoquinolyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, a benzothiophenyl group, a benzothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzothiorolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, or an azadibenzothiorolyl group; or
[0132] -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2), and
[0133] Q1 to Q3 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl group; cyano group; nitro group; C1-C 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 Alkynyl group; C1-C 60 Alkoxy group; or each unsubstituted or deuterated, -F, cyano group, C1-C 60 Alkyl groups, C1-C 60 C3-C substituted by an alkoxy group, a phenyl group, a biphenyl group or any combination thereof 60 Carbocyclic group or C1-C 60 Heterocyclic group.
[0134] In an embodiment, Ar2, Ar3 and R5 to R7 may each independently be:
[0135] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 20 Alkyl group or C1-C 20 alkoxy groups;
[0136] Each is deuterated, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, C1-C 10 C1-C12 substituted with an alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group, a pyrimidinyl group, or any combination thereof 20 Alkyl group or C1-C 20 alkoxy groups;
[0137] Each unsubstituted or deuterated, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, C1-C 10 Alkylphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, yl group, pyrrolyl group, thienyl group, furyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolyl group, isoquinolyl group, benzoquinolyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazole group, a benzothiophene group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophene group, a benzocarbazolyl group, a dibenzothioyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidinyl group, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32),-P(Q 31 )(Q 32 ),-C(=O)(Q 31 )、-S(=O)2(Q 31 ),-P(=O)(Q 31 )(Q 32 ) or any combination thereof substituted cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, C1-C 10 Alkylphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, yl group, pyrrolyl group, thienyl group, furyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolyl group, isoquinolyl group, benzoquinolyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, a benzothiophenyl group, a benzothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzothiorolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, or an azadibenzothiorolyl group; or
[0138] -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2), and
[0139] Q1 to Q3 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl group; cyano group; nitro group; C1-C 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 Alkynyl group; C1-C 60 Alkoxy group; or each unsubstituted or deuterated, -F, cyano group, C1-C 60 Alkyl groups, C1-C 60C3-C substituted by an alkoxy group, a phenyl group, a biphenyl group or any combination thereof 60 Carbocyclic group or C1-C 60 Heterocyclic group.
[0140] In an embodiment, R 32 to R 34 and R 42 to R 44 At least one of them may each independently be a group represented by Formula 2.
[0141] In an embodiment, R 41 to R 44 At least one of may be each independently a group represented by Formula 2, and
[0142] R 31 to R 34 can each independently be hydrogen or deuterium.
[0143] In an embodiment, the heterocyclic compound may be represented by one of Formula 1-1 to Formula 1-4:
[0144]
[0145] In Formulas 1-1 to 1-4,
[0146] L1, a1, Ar1, R 21 to R 24 、R 31 to R 34 and R 41 to R 44 may each be the same as described herein, and
[0147] R 11 to R 14 and R1 in Formula 1.
[0148] In an embodiment, the heterocyclic compound can be one of Compound 1 to Compound 70:
[0149]
[0150]
[0151]
[0152]
[0153]
[0154]
[0155]
[0156]
[0157] In an embodiment, the heterocyclic compound represented by Formula 1 may have a structure in which two carbazole moieties are directly connected to each other and a third carbazole moiety for increasing the hole migration speed is connected at the ortho position of the phenyl linker, and has a high triplet energy level of greater than or equal to about 2.75 eV by reducing the degree of triplet energy level reduction compared to a structure in which the third carbazole moiety is connected at the meta or para position of the phenyl linker.
[0158] Therefore, a light-emitting device including the heterocyclic compound can have low driving voltage and excellent light-emitting efficiency.
[0159] By referring to the synthesis examples and / or working examples provided below, one of ordinary skill in the art can recognize the synthesis method of the heterocyclic compound represented by Formula 1.
[0160] At least one heterocyclic compound represented by Formula 1 may be included in a light-emitting device (e.g., an organic light-emitting device). In the embodiment, the light-emitting device may include: a first electrode; a second electrode facing the first electrode; an intermediate layer between the first electrode and the second electrode and including an emission layer; and a heterocyclic compound represented by Formula 1.
[0161] In an embodiment,
[0162] The first electrode of the light emitting device may be an anode,
[0163] The second electrode of the light emitting device may be a cathode, and
[0164] The intermediate layer of the light emitting device may further include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode, wherein
[0165] The hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof, and
[0166] The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0167] In an embodiment, the light emitting device may have a triplet energy level greater than or equal to about 2.75 eV. For example, the triplet energy level of the light emitting device may be greater than or equal to about 2.8 eV.
[0168] In the embodiment, the heterocyclic compound represented by Formula 1 may be included between the first electrode and the second electrode of the light emitting device.
[0169] In the embodiment, the heterocyclic compound represented by Formula 1 may be included in a hole injection layer, a hole transport layer, an electron injection layer, or an electron transport layer of a light emitting device.
[0170] In the embodiment, an intermediate layer of the light emitting device, for example, an emission layer, may include the heterocyclic compound represented by Formula 1.
[0171] In the embodiment, the emission layer of the light emitting device may include a dopant and a host, and the dopant may include a heterocyclic compound represented by Formula 1. For example, the heterocyclic compound represented by Formula 1 may be used as the dopant.
[0172] In the embodiment, the emission layer of the light-emitting device may include a dopant and a host, and the host may include a heterocyclic compound represented by Formula 1. For example, the heterocyclic compound represented by Formula 1 may be used as a host. For example, the heterocyclic compound represented by Formula 1 may be used as a phosphorescent host of the light-emitting device.
[0173] In the embodiment, the emission layer in the intermediate layer of the light-emitting device may include a dopant and a host, and the heterocyclic compound represented by Formula 1 may be used as a thermally activated delayed fluorescence (TADF) dopant of the light-emitting device.
[0174] In the embodiment, the emission layer in the intermediate layer of the light-emitting device may include a dopant and a host, and the heterocyclic compound represented by Formula 1 may be used as a TADF host of the light-emitting device. Further details about the emission layer and the dopant may be the same as described herein.
[0175] In the embodiment, the emission layer of the light emitting device may include the heterocyclic compound represented by Formula 1, and any one of the red layer, green layer, blue layer, and white layer of the emission layer may include the heterocyclic compound represented by Formula 1.
[0176] In the embodiment, the light emitting device may further include a capping layer outside the first electrode and / or a capping layer outside the second electrode.
[0177] For example, the light-emitting device may further include at least one of a first covering layer outside the first electrode and a second covering layer outside the second electrode, wherein at least one of the first covering layer and the second covering layer may include a heterocyclic compound represented by Formula 1. Further details regarding the first covering layer and / or the second covering layer may be the same as described herein.
[0178] In the embodiment, the light emitting device may further include a first capping layer outside the first electrode. For example, the first capping layer may include a heterocyclic compound represented by Formula 1.
[0179] In the embodiment, the light emitting device may further include a second capping layer outside the second electrode. For example, the second capping layer may include a heterocyclic compound represented by Formula 1.
[0180] In the embodiment, the light-emitting device may further include a first covering layer outside the first electrode and a second covering layer outside the second electrode. For example, at least one of the first covering layer and the second covering layer may each independently contain a heterocyclic compound represented by Formula 1. As used herein, the expression "(the intermediate layer and / or the covering layer) contains at least one heterocyclic compound" may be interpreted as "(the intermediate layer and / or the covering layer) may contain one type of heterocyclic compound represented by Formula 1 or two or more different types of heterocyclic compounds each independently represented by Formula 1".
[0181] For example, the intermediate layer and / or the covering layer may contain only Compound 1 as the heterocyclic compound, wherein Compound 1 is a heterocyclic compound represented by Formula 1. In an embodiment, Compound 1 may be present in the emission layer of the light-emitting device. In an embodiment, the intermediate layer may contain Compound 1 and Compound 2, which is another heterocyclic compound represented by Formula 1. In an embodiment, Compound 1 and Compound 2 may be present in the same layer (for example, both Compound 1 and Compound 2 may be present in the emission layer), or may be present in different layers (for example, Compound 1 may be present in the emission layer, and Compound 2 may be present in the electron transport region).
[0182] In the specification, the term "intermediate layer" may refer to a single layer and / or a plurality of layers between a first electrode and a second electrode of a light emitting device.
[0183] According to another embodiment, an electronic device may include the light-emitting device. The electronic device may further include a thin film transistor. For example, the electronic device may further include a thin film transistor, the thin film transistor including a source electrode and a drain electrode, wherein the first electrode of the light-emitting device may be electrically coupled to the source electrode or the drain electrode. In an embodiment, the electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof. Further details regarding the electronic device may be the same as described herein.
[0184] [ Figure 1 Description]
[0185] Figure 1 is a schematic cross-sectional view of a light emitting device 10 according to the embodiment. The light emitting device 10 includes a first electrode 110 , an intermediate layer 130 , and a second electrode 150 .
[0186] In the following, reference will be made to Figure 1 The structure of the light emitting device 10 and a method of manufacturing the light emitting device 10 according to the embodiment are described.
[0187] [First electrode 110]
[0188] exist Figure 1 In the embodiment, the substrate may be further included under the first electrode 110 or on the second electrode 150. In an embodiment, the substrate may be a glass substrate or a plastic substrate. In an embodiment, the substrate may be a flexible substrate and may include a plastic having excellent heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.
[0189] The first electrode 110 may be formed by, for example, depositing or sputtering a material on a substrate for forming the first electrode 110. When the first electrode 110 is an anode, the material for forming the first electrode 110 may be a high work function material that facilitates hole injection.
[0190] The first electrode 110 may be a reflective electrode, a semi-transmissive reflective electrode, or a transmissive electrode. In an embodiment, when the first electrode 110 is a transmissive electrode, the material used to form the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. In an embodiment, when the first electrode 110 is a semi-transmissive reflective electrode or a reflective electrode, the material used to form the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.
[0191] The first electrode 110 may have a single-layer structure consisting of a single layer or a multi-layer structure including a plurality of layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO.
[0192] [Middle layer 130]
[0193] The intermediate layer 130 may be disposed on the first electrode 110. The intermediate layer 130 may include an emission layer.
[0194] The intermediate layer 130 may further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 150 .
[0195] In addition to various organic materials, the intermediate layer 130 may further include a metal-containing compound (eg, an organometallic compound), an inorganic material (eg, quantum dots), and the like.
[0196] In the embodiment, the intermediate layer 130 may include two or more emission units stacked between the first electrode 110 and the second electrode 150, and at least one charge generation layer between adjacent units of the two or more emission units. When the intermediate layer 130 includes two or more emission units and at least one charge generation layer as described above, the light-emitting device 10 may be a tandem light-emitting device.
[0197] [Hole Transport Region in Intermediate Layer 130]
[0198] The hole transport region may have a single-layer structure composed of a layer composed of a material, a single-layer structure composed of a layer containing different materials, or a multi-layer structure including a plurality of layers containing different materials.
[0199] The hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof.
[0200] In an embodiment, the hole transport region may have a multi-layer structure, including a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission assisting layer structure, a hole injection layer / emission assisting layer structure, a hole transport layer / emission assisting layer structure, or a hole injection layer / hole transport layer / emission assisting layer structure, wherein the layers of each structure may be stacked from the first electrode 110 in their respective prescribed order, but the structure of the hole transport region is not limited thereto.
[0201] In an embodiment, the hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
[0202] [Formula 201]
[0203]
[0204] [Formula 202]
[0205]
[0206] In Equations 201 and 202,
[0207] L 201 To L 204 may be each independently unsubstituted or substituted with at least one R 10a Substituted divalent C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted divalent C1-C 60 Heterocyclic groups,
[0208] L 205 Can be *-O-*', *-S-*', *-N(Q201 )-*', unsubstituted or replaced by at least one R 10a Substituted C1-C 20 Alkylene group, unsubstituted or substituted by at least one R 10a Substituted C2-C 20 Alkenylene group, unsubstituted or substituted with at least one R 10a Substituted divalent C3-C 60 Carbocyclic groups, either unsubstituted or substituted with at least one R 10a Substituted divalent C1-C 60 A heterocyclic group, wherein * and *' each represent a binding site to an adjacent atom,
[0209] xa1 to xa4 may each independently be an integer from 0 to 5,
[0210] xa5 can be an integer from 1 to 10,
[0211] R 201 to R 204 and Q 201 may be each independently unsubstituted or substituted with at least one R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups,
[0212] R 201 and R 202 may be optionally substituted via a single bond, unsubstituted or substituted by at least one R 10a Substituted C1-C5 alkylene groups or unsubstituted or replaced by at least one R 10a The substituted C2-C5 alkenylene groups are linked to each other to form an unsubstituted or substituted C2-C5 alkenyl group. 10a Replaced C8-C 60 Polycyclic groups (e.g., carbazole groups, etc.) (e.g., compound HT16, etc.),
[0213] R 203 and R 204 may be optionally substituted via a single bond, unsubstituted or substituted by at least one R 10a Substituted C1-C5 alkylene groups or unsubstituted or replaced by at least one R 10a The substituted C2-C5 alkenylene groups are linked to each other to form an unsubstituted or substituted C2-C5 alkenyl group. 10a Replaced C8-C 60 Polycyclic groups, and
[0214] na1 can be an integer from 1 to 4, and R 10a Can be the same as described herein.
[0215] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each include at least one of the groups represented by Formulas CY201 to CY217:
[0216]
[0217] In formulas CY201 to CY217, R 10b and R 10c can be independently compared with R 10a Same as described, CY 201 To Ring CY 204 Can be C3-C independently 20 Carbocyclic group or C1-C 20 heterocyclic group, and at least one hydrogen in Formula CY201 to Formula CY217 may be unsubstituted or replaced by R 10a replace.
[0218] In an embodiment, in Formula CY201 to Formula CY217, ring CY 201 To Ring CY 204 Each may independently be a phenyl group, a naphthalene group, a phenanthrene group or an anthracene group.
[0219] In the embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each independently include at least one of the groups represented by Formula CY201 to Formula CY203.
[0220] In an embodiment, the compound represented by Formula 201 may include at least one of the groups represented by Formula CY201 to Formula CY203 and at least one of the groups represented by Formula CY204 to Formula CY217.
[0221] In an embodiment, in Formula 201, xa1 may be 1, R 201 may be one of the groups represented by formula CY201 to formula CY203, xa2 may be 0, and R 202 It may be one of the groups represented by formula CY204 to formula CY207.
[0222] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include the group represented by Formula CY201 to Formula CY203.
[0223] In the embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include the group represented by Formula CY201 to Formula CY203, and may each independently include at least one of the groups represented by Formula CY204 to Formula CY217.
[0224] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include the group represented by Formula CY201 to Formula CY217.
[0225] In an embodiment, the hole transport region may include one of Compound HT1 to Compound HT46, m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), or any combination thereof:
[0226]
[0227]
[0228]
[0229]
[0230]
[0231] The thickness of the hole transport region can be about to about For example, the thickness of the hole transport region may be about to about When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer may be about to about And the thickness of the hole transport layer can be about to about For example, the thickness of the hole injection layer may be about to about For example, the thickness of the hole transport layer may be about to about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics can be obtained without a significant increase in driving voltage.
[0232] The emission-assisting layer can increase light emission efficiency by compensating the optical resonance distance according to the wavelength of light emitted by the emission layer, and the electron blocking layer can block electrons from leaking from the emission layer to the hole transport region. Materials that can be included in the hole transport region can be included in the emission-assisting layer and the electron blocking layer.
[0233] [p-dopant]
[0234] In addition to the above materials, the hole transport region may further contain a charge generating material for improving the conductive properties. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region (eg, in the form of a single layer composed of the charge generating material).
[0235] The charge generating material may be, for example, a p-dopant.
[0236] In an embodiment, the p-dopant can have a lowest unoccupied molecular orbital (LUMO) energy level of less than or equal to about -3.5 eV.
[0237] In an embodiment, the p-dopant may include a quinone derivative, a compound containing a cyano group, a compound including the element EL1 and the element EL2, or any combination thereof.
[0238] Examples of the quinone derivative may include TCNQ, F4-TCNQ, and the like.
[0239] Examples of the cyano group-containing compound may include HAT-CN, a compound represented by Formula 221, and the like:
[0240]
[0241] [Formula 221]
[0242]
[0243] In formula 221,
[0244] R 221 to R 223 may be each independently unsubstituted or substituted with at least one R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, where R 10a can be the same as described herein, and
[0245] R 221 to R 223At least one of them can be independently each of: a cyano group; -F; -Cl; -Br; -I; a C1-C1-substituted group substituted with a cyano group, -F, -Cl, -Br, -I or any combination thereof 20 Alkyl group; or any combination thereof substituted C3-C 60 Carbocyclic group or C1-C 60 Heterocyclic group.
[0246] In the compound including the element EL1 and the element EL2, the element EL1 may be a metal, a metalloid, or any combination thereof, and the element EL2 may be a nonmetal, a metalloid, or any combination thereof.
[0247] Examples of metals may include alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt ( (e.g., Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au) etc.); late transition metals (e.g., zinc (Zn), indium (In), tin (Sn) etc.); lanthanide metals (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu) etc.); etc.
[0248] Examples of the metalloid may include silicon (Si), antimony (Sb), tellurium (Te), and the like.
[0249] Examples of non-metals may include oxygen (O), halogens (eg, F, Cl, Br, I, etc.), and the like.
[0250] For example, the compound containing element EL1 and element EL2 may include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides, metal iodides, etc.), metalloid halides (e.g., metalloid fluorides, metalloid chlorides, metalloid bromides, metalloid iodides, etc.), metal tellurides, or any combination thereof.
[0251] Examples of metal oxides may include tungsten oxides (e.g., WO, W2O3, WO2, WO3, W2O5, etc.), vanadium oxides (e.g., VO, V2O3, VO2, V2O5, etc.), molybdenum oxides (e.g., MoO, Mo2O3, MoO2, MoO3, Mo2O5, etc.), rhenium oxides (e.g., ReO3, etc.), etc.
[0252] Examples of the metal halide may include alkali metal halides, alkaline earth metal halides, transition metal halides, late transition metal halides, lanthanide metal halides, and the like.
[0253] Examples of alkali metal halides may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, CsI, and the like.
[0254] Examples of alkaline earth metal halides may include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, BaI2, etc.
[0255] Examples of transition metal halides may include titanium halides (e.g., TiF4, TiCl4, TiBr4, TiI4, etc.), zirconium halides (e.g., ZrF4, ZrCl4, ZrBr4, ZrI4, etc.), hafnium halides (e.g., HfF4, HfCl4, HfBr4, HfI4, etc.), vanadium halides (e.g., VF3, VCl3, VBr3, VI3, etc.), niobium halides (e.g., NbF3, NbCl3, NbBr3, NbI3, etc.), tantalum halides (e.g., TaF3, TaCl3, T aBr3, TaI3, etc.), chromium halides (e.g., CrF3, CrCl3, CrBr3, CrI3, etc.), molybdenum halides (e.g., MoF3, MoCl3, MoBr3, MoI3, etc.), tungsten halides (e.g., WF3, WCl3, WBr3, WI3, etc.), manganese halides (e.g., MnF2, MnCl2, MnBr2, MnI2, etc.), technetium halides (e.g., TcF2, TcCl2, TcBr2, TcI2, etc.), rhenium halides (e.g., ReF2, ReCl2, ReBr 2, ReI2, etc.), iron halides (e.g., FeF2, FeCl2, FeBr2, FeI2, etc.), ruthenium halides (e.g., RuF2, RuCl2, RuBr2, RuI2, etc.), osmium halides (e.g., OsF2, OsCl2, OsBr2, OsI2, etc.), cobalt halides (e.g., CoF2, CoCl2, CoBr2, CoI2, etc.), rhodium halides (e.g., RhF2, RhCl2, RhBr2, RhI2, etc.), iridium halides (e.g., IrF2, IrCl2, IrBr2, etc.), r2, IrI2, etc.), nickel halides (e.g., NiF2, NiCl2, NiBr2, NiI2, etc.), palladium halides (e.g., PdF2, PdCl2, PdBr2, PdI2, etc.), platinum halides (e.g., PtF2, PtCl2, PtBr2, PtI2, etc.), copper halides (e.g., CuF, CuCl, CuBr, CuI, etc.), silver halides (e.g., AgF, AgCl, AgBr, AgI, etc.), gold halides (e.g., AuF, AuCl, AuBr, AuI, etc.), etc.
[0256] Examples of late transition metal halides may include zinc halides (eg, ZnF2, ZnCl2, ZnBr2, ZnI2, etc.), indium halides (eg, InI3, etc.), tin halides (eg, SnI2, etc.), and the like.
[0257] Examples of lanthanide metal halides may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, SmI3, and the like.
[0258] Examples of the metalloid halide may include antimony halide (eg, SbCl 5 , etc.) and the like.
[0259] Examples of metal tellurides may include alkali metal tellurides (e.g., Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metal tellurides (e.g., TiTe2, ZrTe2, HfTe2, V2Te3, Nb2Te3, Ta2Te3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, F eTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe, Au2Te, etc.), late transition metal tellurides (for example, ZnTe, etc.), lanthanide metal tellurides (for example, LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.), etc.
[0260] [Emitting Layer in Intermediate Layer 130]
[0261] When the light-emitting device 10 is a full-color light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and / or a blue emission layer according to the sub-pixel. In an embodiment, the emission layer may have a stacked structure in which two or more layers of the red emission layer, the green emission layer, and the blue emission layer may be in contact with each other or may be separated from each other to emit white light. In an embodiment, the emission layer may have a structure in which two or more materials of a red light-emitting material, a green light-emitting material, and a blue light-emitting material may be mixed with each other in a single layer to emit white light.
[0262] In an embodiment, the emissive layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.
[0263] The amount of the dopant in the emission layer may be about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host.
[0264] In an embodiment, the emissive layer may comprise quantum dots.
[0265] In an embodiment, the emissive layer may include a delayed fluorescent material. The delayed fluorescent material may be used as a host or a dopant in the emissive layer.
[0266] The thickness of the emission layer can be about to about For example, the thickness of the emissive layer can be about to about When the thickness of the emission layer 130 is within any of these ranges, excellent light emitting characteristics may be obtained without a significant increase in driving voltage.
[0267] [main body]
[0268] In an embodiment, the host may include a heterocyclic compound represented by Formula 1.
[0269] The host may further include a compound represented by Formula 301:
[0270] [Equation 301]
[0271] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21
[0272] In formula 301,
[0273] Ar 301 may be unsubstituted or substituted with at least one R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, and L 301 may be unsubstituted or substituted with at least one R 10a Substituted divalent C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted divalent C1-C 60 Heterocyclic groups,
[0274] xb11 can be 1, 2 or 3,
[0275] xb1 can be an integer from 0 to 5,
[0276] R 301 It can be hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or replaced by at least one R 10a Substituted C1-C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10aSubstituted C1-C 60 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Heterocyclic group, -Si(Q 301 )(Q 302 )(Q 303 )、-N(Q 301 )(Q 302 )、-B(Q 301 )(Q 302 ),-C(=O)(Q 301 )、-S(=O)2(Q 301 ) or -P(=O)(Q 301 )(Q 302 ),
[0277] xb21 can be an integer from 1 to 5, and
[0278] Q 301 To Q 303 can each independently be the same as described for Q1, and R 10a Can be the same as described herein.
[0279] In an embodiment, in Formula 301, when xb11 is 2 or greater, two or more Ar 301 can be connected to each other via a single bond.
[0280] In an embodiment, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
[0281] [Formula 301-1]
[0282]
[0283] [Formula 301-2]
[0284]
[0285] In Formula 301-1 and Formula 301-2,
[0286] Ring A 301 To Ring A 304 may be each independently unsubstituted or substituted with at least one R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, where R 10acan be the same as described in this article,
[0287] X 301 Can be O, S, N[(L 304 ) xb4 -R 304 ]、C(R 304 )(R 305 ) or Si(R 304 )(R 305 ),
[0288] xb22 and xb23 can each independently be 0, 1 or 2,
[0289] L 301 , xb1 and R 301 may each be the same as described herein,
[0290] L 302 To L 304 Can be independently compared with L 301 Same as described,
[0291] xb2 to xb4 may each independently be the same as described with respect to xb1, and
[0292] R 302 to R 305 and R 311 to R 314 can be independently compared with R 301 Same as described.
[0293] In embodiments, the host may include an alkaline earth metal complex, a late transition metal complex, or any combination thereof. In embodiments, the host may include a Be complex (eg, Compound H55), a Mg complex, a Zn complex, or any combination thereof.
[0294] In an embodiment, the host may include one of Compound H1 to Compound H128, 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), 9,10-di(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-di(9-carbazolyl)benzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), or any combination thereof:
[0295]
[0296]
[0297]
[0298]
[0299]
[0300]
[0301]
[0302] [Phosphorescent dopant]
[0303] In an embodiment, the phosphorescent dopant may include at least one transition metal as a central metal.
[0304] The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.
[0305] The phosphorescent dopant may be electrically neutral.
[0306] In an embodiment, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
[0307] [Formula 401]
[0308] M(L 401 ) xc1 (L 402 ) xc2
[0309] [Formula 402]
[0310]
[0311] In Equations 401 and 402,
[0312] M can be a transition metal (e.g., Ir, Pt, Pd, Os, Ti, Au, Hf, Eu, Tb, Rh, Re, or Tm),
[0313] L 401 The ligand may be a ligand represented by formula 402, and xc1 may be 1, 2, or 3, wherein when xc1 is 2 or greater, two or more L 401 can be the same as or different from each other,
[0314] L 402 can be an organic ligand, and xc2 can be 0, 1, 2, 3 or 4, wherein when xc2 is 2 or greater than 2, two or more L 402 can be the same or different from each other,
[0315] X 401 and X 402 may each independently be nitrogen or carbon,
[0316] Ring A 401 and Ring A 402 Can be C3-C independently 60 Carbocyclic group or C1-C 60 Heterocyclic groups,
[0317] T 401 It can be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 411 )-*'、*-C(Q 411 )(Q 412 )-*'、*-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 )=*' or *=C=*', wherein * and *' each represent a binding site with an adjacent atom,
[0318] X 403 and X 404 can each independently be a chemical bond (eg, a covalent bond or a coordinate bond), O, S, N (Q 413 )、B(Q 413 )、P(Q 413 )、C(Q 413 )(Q 414 ) or Si(Q 413 )(Q 414 ),
[0319] Q 411 To Q 414 can each be independently the same as described for Q1,
[0320] R 401 and R 402 can be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted by at least one R 10a Substituted C1-C 20 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C1-C 20 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Heterocyclic group, -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q401 )(Q 402 ),-C(=O)(Q 401 )、-S(=O)2(Q 401 ) or -P(=O)(Q 401 )(Q 402 ), where R 10a can be the same as described in this article,
[0321] Q 401 To Q 403 can each be independently the same as described for Q1,
[0322] xc11 and xc12 may each independently be an integer from 0 to 10, and
[0323] * and *' in Formula 402 each represent a binding site with M in Formula 401.
[0324] For example, in Equation 402, X 401 can be nitrogen, and X 402 It can be carbon, or X 401 and X 402 Each may be nitrogen.
[0325] In an embodiment, in Formula 401, when xc1 is 2 or greater than 2, two or more L 401 The two rings A 401 It can optionally be connected via T as a linker 402 connected to each other, and two or more L 401 The two rings A 402 It can optionally be connected via T as a linker 403 connected to each other (see Compound PD1 to Compound PD4 and Compound PD7). 402 and T 403 Can be independently compared with T 401 Same as described.
[0326] In formula 401, L 402 It can be an organic ligand. For example, L 402 It may include a halogen group, a diketone group (e.g., an acetylacetonate group), a carboxylic acid group (e.g., a picolinate group), -C(=O), an isonitrile group, -CN, a phosphorus-containing group (e.g., a phosphine group, a phosphite group, etc.), or any combination thereof.
[0327] In an embodiment, the phosphorescent dopant may include, for example, one of Compound PD1 to Compound PD39 or any combination thereof:
[0328]
[0329]
[0330]
[0331]
[0332] [Fluorescent dopant]
[0333] The fluorescent dopant may include an amine group-containing compound, a styryl group-containing compound, or any combination thereof.
[0334] In an embodiment, the fluorescent dopant may include a compound represented by Formula 501:
[0335] [Formula 501]
[0336]
[0337] In formula 501,
[0338] Ar 501 、R 501 and R 502 may be each independently unsubstituted or substituted with at least one R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, and L 501 To L 503 may be each independently unsubstituted or substituted with at least one R 10a Substituted divalent C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted divalent C1-C 60 Heterocyclic group, where R 10a can be the same as described in this article,
[0339] xd1 to xd3 may each independently be 0, 1, 2 or 3, and
[0340] xd4 can be 1, 2, 3, 4, 5 or 6.
[0341] In an embodiment, in Formula 501, Ar 501 It may be a fused cyclic group in which three or more monocyclic groups are fused together (e.g., anthracene group, group, pyrene group, etc.).
[0342] In an embodiment, in Formula 501, xd4 can be 2.
[0343] In an embodiment, the fluorescent dopant may include one of compounds FD1 to FD37, DPVBi, DPAVBi, or any combination thereof:
[0344]
[0345]
[0346]
[0347] [Delayed fluorescence material]
[0348] In an embodiment, the emissive layer may include a delayed fluorescent material.
[0349] In the specification, the delayed fluorescent material may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.
[0350] The delayed fluorescent material included in the emission layer may serve as a host or as a dopant depending on the types of other materials included in the emission layer.
[0351] In the embodiment, the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material may be about 0 eV to about 0.5 eV. When the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material satisfies the above range, up-conversion of the delayed fluorescent material from the triplet state to the singlet state can be effectively performed, and thus the light-emitting device 10 can have improved luminous efficiency.
[0352] In an embodiment, the delayed fluorescent material may include: a molecule comprising at least one electron donor (eg, a π-electron-rich C3-C 60 Cyclic groups, such as carbazole groups, etc.) and at least one electron acceptor (e.g., sulfoxide groups, cyano groups, π-electron-deficient nitrogen-containing C1-C 60 and / or a C8-C ... 60 Polycyclic materials.
[0353] In an embodiment, the delayed fluorescent material may include, for example, at least one of Compound DF1 to Compound DF14:
[0354]
[0355]
[0356] quantum dots
[0357] In an embodiment, the emissive layer may comprise quantum dots.
[0358] In the specification, a "quantum dot" may be a crystal of a semiconductor compound, and may include any material capable of emitting light of various emission wavelengths depending on the size of the crystal.
[0359] The diameter of the quantum dots can be, for example, from about 1 nm to about 10 nm.
[0360] Quantum dots can be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, or any process similar thereto.
[0361] The wet chemical process involves mixing precursor materials with an organic solvent and growing quantum dot particle crystals. As the crystals grow, the organic solvent naturally acts as a dispersant that coordinates to the surface of the quantum dot crystals and controls their growth. This allows the growth of quantum dot particles to be controlled using a process that is less expensive and easier to perform than vapor deposition methods such as metal-organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE).
[0362] The quantum dots may include Group II-VI semiconductor compounds, Group III-V semiconductor compounds, Group III-VI semiconductor compounds, Group I-III-VI semiconductor compounds, Group IV-VI semiconductor compounds, Group IV elements or compounds, or any combination thereof.
[0363] Examples of II-VI semiconductor compounds may include binary compounds such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, etc.; ternary compounds such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, Cd ZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS, etc.; quaternary compounds, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, etc.; or any combination thereof.
[0364] Examples of III-V semiconductor compounds may include binary compounds such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, etc.; ternary compounds such as GaNPs, GaNAs, GaNSb, GaPAs, GaPSb, AlNPs, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNPs, InAlP, InNAs, InNSb, InPAs, InPSb, etc.; quaternary compounds such as GaAlNPs, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNPs, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNPs, InAlNAs, InAlNSb, InAlPAs, InAlPSb, etc.; or any combination thereof. In embodiments, the III-V semiconductor compound may further include a Group II element. Examples of the Group III-V semiconductor compound further including a Group II element may include InZnP, InGaZnP, InAlZnP, and the like.
[0365] Examples of III-VI semiconductor compounds may include: binary compounds, such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3, InTe, etc.; ternary compounds, such as InGaS3, InGaSe3, etc.; or any combination thereof.
[0366] Examples of Group I-III-VI semiconductor compounds may include: ternary compounds such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, AgAlO2, etc.; or any combination thereof.
[0367] Examples of IV-VI semiconductor compounds may include: binary compounds, such as SnS, SnSe, SnTe, PbS, PbSe or PbTe; ternary compounds, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, etc.; quaternary compounds, such as SnPbSSe, SnPbSeTe, SnPbSTe, etc.; or any combination thereof.
[0368] Examples of Group IV elements or compounds may include: single element materials, such as Si, Ge, etc.; binary compounds, such as SiC, SiGe, etc.; or any combination thereof.
[0369] Each element contained in the compound (eg, binary compound, ternary compound, or quaternary compound) may be present in the particle at a uniform concentration or at a non-uniform concentration.
[0370] In an embodiment, the quantum dot may have a single structure in which the concentration of each element in the quantum dot is uniform, or the quantum dot may have a core-shell structure. In an embodiment, when the quantum dot has a core-shell structure, the material contained in the core and the material contained in the shell may be different from each other.
[0371] The shell of a quantum dot can serve as a protective layer to prevent chemical denaturation of the core to maintain semiconductor properties and / or as a charging layer to impart electrophoretic properties to the quantum dot. The shell can be single-layer or multi-layer. The interface between the core and the shell can have a concentration gradient, where the concentration of the material in the shell decreases towards the core.
[0372] Examples of the shell of the quantum dot may include metal oxides, metalloid oxides, non-metal oxides, semiconductor compounds, or any combination thereof. Examples of metal oxides, metalloid oxides, or non-metal oxides may include binary compounds such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, NiO, etc.; ternary compounds such as MgAl2O4, CoFe2O4, NiFe2O4, CoMn2O4, etc.; or any combination thereof.
[0373] Examples of semiconductor compounds may include, as described above: II-VI semiconductor compounds; III-V semiconductor compounds; III-VI semiconductor compounds; I-III-VI semiconductor compounds; IV-VI semiconductor compounds, or any combination thereof. Examples of semiconductor compounds include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.
[0374] The full width at half maximum (FWHM) of the emission wavelength spectrum of the quantum dot can be less than or equal to about 45 nm. For example, the FWHM of the emission wavelength spectrum of the quantum dot can be less than or equal to about 40 nm. For example, the FWHM of the emission wavelength spectrum of the quantum dot can be less than or equal to about 30 nm. When the quantum dot has a FWHM of an emission wavelength spectrum within any of these ranges, the color purity or color reproducibility of the quantum dot can be improved. The light emitted by the quantum dot can be emitted in all directions, so that the wide viewing angle can be improved.
[0375] In embodiments, the quantum dots may be nanoparticles, nanotubes, nanowires, nanofibers, nanoplates, etc., or the quantum dots may be in the form of spherical nanoparticles, pyramidal nanoparticles, multi-armed nanoparticles, or cubic nanoparticles.
[0376] By controlling the size of the quantum dots, the energy band gap can be adjusted so that light with various wavelength bands can be obtained from the emission layer containing the quantum dots. Therefore, by using quantum dots of different sizes, a light-emitting device that emits light of various wavelengths can be realized. In embodiments, the size of the quantum dots can be adjusted to emit red light, green light, and / or blue light. In embodiments, the size of the quantum dots can be configured to emit white light by combining light of various colors.
[0377] [Electron Transport Region in Intermediate Layer 130]
[0378] The electron transport region may have a single-layer structure consisting of a layer composed of a single material, a single-layer structure consisting of layers containing different materials, or a multi-layer structure including a plurality of layers containing different materials.
[0379] The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0380] In an embodiment, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein the layers of each structure may be stacked from the emission layer in their respective prescribed order, but the structure of the electron transport region is not limited thereto.
[0381] In an embodiment, the electron transport region (eg, a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a nitrogen-containing C1-C1-C2-containing polymer having at least one π-electron-deficient carbonyl group. 60 Metal-free compounds of cyclic groups.
[0382] In an embodiment, the electron transport region may include a compound represented by Formula 601:
[0383] [Equation 601]
[0384] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21
[0385] In Equation 601,
[0386] Ar 601may be unsubstituted or substituted with at least one R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, and L 601 may be unsubstituted or substituted with at least one R 10a Substituted divalent C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted divalent C1-C 60 Heterocyclic groups,
[0387] xe11 can be 1, 2 or 3,
[0388] xe1 can be 0, 1, 2, 3, 4, or 5,
[0389] R 601 may be unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Heterocyclic group, -Si(Q 601 )(Q 602 )(Q 603 ),-C(=O)(Q 601 )、-S(=O)2(Q 601 ) or -P(=O)(Q 601 )(Q 602 ), Q 601 To Q 603 can each be independently the same as described for Q1,
[0390] xe21 can be 1, 2, 3, 4, or 5, and
[0391] At least one of the following conditions can be met: 601 may be unsubstituted or substituted with at least one R 10a Substituted π-electron-deficient nitrogen-containing C1-C 60 Cyclic group, R 601 may be unsubstituted or substituted with at least one R 10a Substituted π-electron-deficient nitrogen-containing C1-C 60 Cyclic groups, and L 601 may be unsubstituted or substituted with at least one R 10a Substituted π-electron-deficient nitrogen-containing divalent C1-C 60 Cyclic group, where R 10a Can be the same as described herein.
[0392] In an embodiment, in Formula 601, when xe11 is 2 or greater, two or more Ar 601 can be connected to each other via a single bond.
[0393] In an embodiment, in Formula 601, Ar 601 may be unsubstituted or substituted with at least one R 10a A substituted anthracene group, wherein R 10a Can be the same as described herein.
[0394] In an embodiment, the electron transport region may include a compound represented by Formula 601-1:
[0395] [Formula 601-1]
[0396]
[0397] In formula 601-1,
[0398] X 614 Can be N or C(R 614 ), X 615 Can be N or C(R 615 ), and X 616 Can be N or C(R 616 ), where X 614 To X 616 At least one of can each be N,
[0399] L 611 To L 613 Can be independently compared with L 601 Same as described,
[0400] xe611 to xe613 can each independently be the same as described for xe1,
[0401] R 611 to R 613 can be independently compared with R 601 Same as described, and
[0402] R 614 to R 616 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a C1-C 20 Alkyl groups, C1-C 20 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic groups, either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, where R10a Can be the same as described herein.
[0403] In an embodiment, in Formula 601 and Formula 601-1, xe1 and xe611 to xe613 may each independently be 0, 1, or 2.
[0404] In an embodiment, the electron transport region may include one of compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, TAZ, NTAZ, or any combination thereof:
[0405]
[0406]
[0407]
[0408]
[0409] The thickness of the electron transport region can be about to about For example, the thickness of the electron transport region may be about to about When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron control layer may be independently about to about And the thickness of the electron transport layer can be about to about For example, the thickness of the buffer layer, the hole blocking layer, or the electron control layer can each independently be about to about For example, the thickness of the electron transport layer can be about to about When the thicknesses of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer, and / or the electron transport region are within these ranges, satisfactory electron transport characteristics may be obtained without a significant increase in driving voltage.
[0410] In addition to the above-mentioned materials, the electron transport region (eg, the electron transport layer in the electron transport region) may further include a metal-containing material.
[0411] The metal-containing material can include an alkali metal complex, an alkaline earth metal complex or any combination thereof. The metal ion of the alkali metal complex can be a Li ion, a Na ion, a K ion, a Rb ion or a Cs ion, and the metal ion of the alkaline earth metal complex can be a Be ion, a Mg ion, a Ca ion, a Sr ion or a Ba ion. The ligand coordinated with the metal ion of the alkali metal complex or the metal ion of the alkaline earth metal complex can include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene or any combination thereof.
[0412] In an embodiment, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (Liq) and / or compound ET-D2:
[0413]
[0414] The electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 150. The electron injection layer may contact (eg, directly contact) the second electrode 150.
[0415] The electron injection layer may have a single-layer structure composed of a layer composed of a single material, a single-layer structure composed of layers containing different materials, or a multilayer structure including a plurality of layers containing different materials.
[0416] In embodiments, the electron injection layer 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 any combination thereof.
[0417] Alkali metals may include Li, Na, K, Rb, Cs, or any combination thereof. Alkaline earth metals may include Mg, Ca, Sr, Ba, or any combination thereof. Rare earth metals may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
[0418] The alkali metal-containing compound, the alkaline earth metal-containing compound, and the rare earth metal-containing compound may be oxides, halides (eg, fluorides, chlorides, bromides, or iodides), or tellurides of alkali metals, alkaline earth metals, and rare earth metals, or any combination thereof.
[0419] The alkali metal-containing compounds can include: alkali metal oxides, such as Li2O, Cs2O or K2O; alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI or KI; or any combination thereof. The alkaline earth metal-containing compounds can include alkaline earth metal oxides, such as BaO, SrO, CaO, Ba x Sr 1-x O (where x is a real number satisfying 0 < x < 1), Ba x Ca 1-x O (where x is a real number satisfying 0 < x < 1), etc. The rare earth metal-containing compounds can include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3 or any combination thereof. In an embodiment, the rare earth metal-containing compounds can include lanthanide metal tellurides. Examples of lanthanide metal tellurides can include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, Lu2Te3, etc.
[0420] The alkali metal complexes, alkaline earth metal complexes and rare earth metal complexes can contain: alkali metal ions, alkaline earth metal ions or rare earth metal ions; and ligands bonded to the metal ions (such as hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline, cyclopentadiene or any combination thereof).
[0421] In an embodiment, the electron injection layer can be composed of: alkali metals, alkaline earth metals, rare earth metals, alkali metal-containing compounds, alkaline earth metal-containing compounds, rare earth metal-containing compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes or any combination thereof as described above. In an embodiment, the electron injection layer can further contain an organic material (for example, a compound represented by Formula 601).
[0422] In an embodiment, the electron injection layer may be composed of an alkali metal-containing compound (e.g., an alkali metal halide); or the electron injection layer may be composed of an alkali metal-containing compound (e.g., an alkali metal halide) and an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. In an embodiment, the electron injection layer may be a KI:Yb co-deposition layer, a RbI:Yb co-deposition layer, a LiF:Yb co-deposition layer, or the like.
[0423] When the electron injection layer further comprises an organic material, alkali metals, alkaline earth metals, rare earth metals, alkali metal-containing compounds, alkaline earth metal-containing compounds, rare earth metal-containing compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes or any combination thereof can be uniformly or non-uniformly dispersed in the matrix comprising the organic material.
[0424] The thickness of the electron injection layer can be about to about For example, the thickness of the electron injection layer may be about to about When the thickness of the electron injection layer is within any of these ranges, satisfactory electron injection characteristics can be obtained without a significant increase in driving voltage.
[0425] [Second electrode 150]
[0426] The second electrode 150 may be disposed on the intermediate layer 130 having the above-described structure. The second electrode 150 may be a cathode serving as an electron injection electrode. When the second electrode 150 is a cathode, the material used to form the second electrode may include a material having a low work function, such as a metal, an alloy, a conductive compound, or any combination thereof.
[0427] The second electrode 150 may include Li, Ag, Mg, Al, Al-Li, Ca, Mg-In, Mg-Ag, Yb, Ag-Yb, ITO, IZO, or any combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive reflective electrode, or a reflective electrode.
[0428] The second electrode 150 may have a single-layer structure or a multi-layer structure.
[0429] [Overlay]
[0430] The light-emitting device 10 may include a first covering layer outside the first electrode 110 and / or a second covering layer outside the second electrode 150. In the embodiment, the light-emitting device 10 may have a structure in which the first covering layer, the first electrode 110, the intermediate layer 130, and the second electrode 150 are stacked in this specified order, a structure in which the first electrode 110, the intermediate layer 130, the second electrode 150 and the second covering layer are stacked in this specified order, or a structure in which the first covering layer, the first electrode 110, the intermediate layer 130, the second electrode 150 and the second covering layer are stacked in this specified order.
[0431] Light generated in the emission layer of the intermediate layer 130 of the light-emitting device 10 can be extracted to the outside through the first electrode 110 (which can be a semi-transmissive reflective electrode or a transmissive electrode) and the first cover layer. Light generated in the emission layer of the intermediate layer 130 of the light-emitting device 10 can be extracted to the outside through the second electrode 150 (which can be a semi-transmissive reflective electrode or a transmissive electrode) and the second cover layer.
[0432] The first cover layer and the second cover layer can each increase external emission efficiency based on the principle of constructive interference, thereby increasing the light extraction efficiency of the light emitting device 10 and improving the luminous efficiency of the light emitting device 10.
[0433] The first cover layer and the second cover layer may each include a material having a refractive index greater than or equal to about 1.6 (relative to a wavelength of about 589 nm).
[0434] The first covering layer and the second covering layer may each independently be an organic covering layer including an organic material, an inorganic covering layer including an inorganic material, or an organic-inorganic composite covering layer including an organic material and an inorganic material.
[0435] At least one of the first covering layer and the second covering layer may each independently comprise a carbocyclic compound, a heterocyclic compound, an amine-containing compound, a porphyrin derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine-containing compound may be optionally substituted with a substituent containing O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof.
[0436] In an embodiment, at least one of the first cover layer and the second cover layer may each independently include an amine group-containing compound.
[0437] In an embodiment, at least one of the first cover layer and the second cover layer may each independently include the compound represented by Formula 201, the compound represented by Formula 202, or any combination thereof.
[0438] In an embodiment, at least one of the first cover layer and the second cover layer may each independently include one of Compound HT28 to Compound HT33, one of Compound CP1 to Compound CP6, β-NPB, or any combination thereof:
[0439]
[0440] [membrane]
[0441] The heterocyclic compound represented by Formula 1 can be included in various films. Therefore, another embodiment of the present disclosure provides a film comprising a heterocyclic compound represented by Formula 1. The film can be, for example, an optical member (or light control device) (e.g., a color filter, a color conversion member, a cover layer, a light extraction efficiency enhancement layer, a selective light absorption layer, a polarizing layer, a layer containing quantum dots, etc.), a light blocking member (e.g., a light reflecting layer, a light absorbing layer, etc.) or a protective member (e.g., an insulating layer, a dielectric layer, etc.).
[0442] [Electronic equipment]
[0443] The light emitting device may be included in various electronic devices. For example, the electronic device including the light emitting device may be a light emitting device, an authentication device, etc.
[0444] In addition to the light-emitting device, the electronic device (e.g., a light-emitting device) may further include a color filter, a color conversion layer, or both a color filter and a color conversion layer. The color filter and / or color conversion layer may be arranged in at least one direction in which the light emitted from the light-emitting device travels. For example, the light emitted from the light-emitting device may be blue light or white light. The light-emitting device may be the same as described herein. In an embodiment, the color conversion layer may include quantum dots. The quantum dots may be, for example, the quantum dots described above.
[0445] The electronic device may include a first substrate, the first substrate may include sub-pixels, the color filter may include color filter regions corresponding to the sub-pixels, and the color conversion layer may include color conversion regions corresponding to the sub-pixels.
[0446] A pixel defining layer may be disposed between the sub-pixels to define each sub-pixel.
[0447] The color filter may further include a color filter region and a light shielding pattern thereon, and the color conversion layer may further include a color conversion region and a light shielding pattern thereon.
[0448] The color filter region (or color conversion region) may include a first region emitting a first color of light, a second region emitting a second color of light, and / or a third region emitting a third color of light, wherein the first color of light, the second color of light, and / or the third color of light may have different maximum emission wavelengths. In an embodiment, the first color of light may be red light, the second color of light may be green light, and the third color of light may be blue light. In an embodiment, the color filter region (or color conversion region) may include quantum dots. For example, the first region may include red quantum dots, the second region may include green quantum dots, and the third region may not include quantum dots. The quantum dots may be the same as described herein. The first region, the second region, and / or the third region may each further include a scatterer.
[0449] In an embodiment, in a light-emitting device that emits a first light, the first region may be designed to absorb the first light to emit a first-first color light, the second region may be designed to absorb the first light to emit a second-first color light, and the third region may be designed to absorb the first light to emit a third-first color light. The first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths from each other. In an embodiment, the first light may be blue light, the first-first color light may be red light, the second-first color light may be green light, and the third-first color light may be blue light.
[0450] In addition to the above-mentioned light-emitting device, the electronic device may further include a thin film transistor. The thin film transistor may include a source electrode, a drain electrode, and an active layer, wherein any one of the source electrode and the drain electrode may be electrically connected to any one of the first electrode 110 and the second electrode 150 of the light-emitting device 10.
[0451] The thin film transistor may further include a gate electrode, a gate insulating film, and the like.
[0452] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, or the like.
[0453] The electronic device may further include a sealing portion for sealing the light-emitting device 10. The sealing portion may be arranged between the color filter and / or color conversion layer and the light-emitting device 10. The sealing portion may allow light from the light-emitting device to be extracted to the outside and may prevent ambient air and / or moisture from penetrating into the light-emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin-film encapsulation layer including at least one of an organic layer and an inorganic layer. When the sealing portion is a thin-film encapsulation layer, the electronic device may be flexible.
[0454] Depending on the purpose of the electronic device, various functional layers may be further included on the seal in addition to the color filter and / or color conversion layer. Examples of functional layers include a touch screen layer and a polarizing layer. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer. The verification device may be, for example, a biometric verification device that verifies an individual by using biometric information of a living being (e.g., a fingertip, pupil, etc.).
[0455] In addition to the light emitting device as described above, the authentication apparatus may further include a biometric information collector.
[0456] The electronic device can be applied to various displays, light sources, lighting equipment, personal computers (for example, mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, electronic game consoles, medical instruments (for example, electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram displays, ultrasonic diagnostic devices or endoscope displays), fish finders, various measuring instruments, meters (for example, meters used for vehicles, aircraft and ships), projectors, etc.
[0457] [Electronic equipment]
[0458] Light emitting devices may be included in various types of electronic equipment.
[0459] For example, the electronic equipment including the light-emitting device can be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a phone, a portable phone, a tablet computer, a tablet phone, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall comprising multiple displays stitched together, a theater screen, a stadium screen, a light therapy device, or a sign.
[0460] The light emitting device may have excellent light emitting efficiency and a long lifespan, and thus electronic equipment including the light emitting device may have characteristics such as high brightness, high resolution, and low power consumption.
[0461] [ Figure 2 and Figure 3 Description]
[0462] Figure 2 is a schematic cross-sectional view of an electronic device according to an embodiment.
[0463] Figure 2The electronic device includes a substrate 100, a thin film transistor (TFT), a light emitting device, and an encapsulation portion 300 that seals the light emitting device.
[0464] The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. The buffer layer 210 may be disposed on the substrate 100. The buffer layer 210 may prevent impurities from penetrating through the substrate 100 and provide a flat surface on the substrate 100.
[0465] The TFT may be disposed on the buffer layer 210. The TFT may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
[0466] The active layer 220 may include an inorganic semiconductor (eg, silicon or polysilicon), an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.
[0467] A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be disposed on the active layer 220 , and the gate electrode 240 may be disposed on the gate insulating film 230 .
[0468] Interlayer insulating film 250 may be disposed on gate electrode 240 . Interlayer insulating film 250 may be disposed between gate electrode 240 and source electrode 260 to insulate gate electrode 240 from source electrode 260 and between gate electrode 240 and drain electrode 270 to insulate gate electrode 240 from drain electrode 270 .
[0469] Source electrode 260 and drain electrode 270 may be disposed on interlayer insulating film 250. Interlayer insulating film 250 and gate insulating film 230 may be formed to expose the source and drain regions of active layer 220, and source electrode 260 and drain electrode 270 may contact the exposed portions of the source and drain regions of active layer 220, respectively.
[0470] The TFT may be electrically connected to the light-emitting device to drive the light-emitting device and may be covered and protected by the passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. The light-emitting device may be provided on the passivation layer 280. The light-emitting device may include a first electrode 110, an intermediate layer 130, and a second electrode 150.
[0471] The first electrode 110 may be disposed on the passivation layer 280. The passivation layer 280 may not completely cover the drain electrode 270 and may expose a portion of the drain electrode 270. The first electrode 110 may be electrically connected to the exposed portion of the drain electrode 270.
[0472] A pixel defining layer 290 including an insulating material may be disposed on the first electrode 110. The pixel defining layer 290 may expose a region of the first electrode 110, and the intermediate layer 130 may be formed in the exposed region of the first electrode 110. The pixel defining layer 290 may be a polyimide-based organic film or a polyacrylic acid-based organic film. Figure 2 Although not shown in the figure, at least some layers of the intermediate layer 130 may extend beyond the upper portion of the pixel defining layer 290 to be provided in the form of a common layer.
[0473] The second electrode 150 may be disposed on the intermediate layer 130, and a capping layer 170 may be further included on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.
[0474] The encapsulation part 300 may be located on the cover layer 170. The encapsulation part 300 may be arranged on the light emitting device to protect the light emitting device from moisture and / or oxygen. The encapsulation part 300 may include an inorganic film including silicon nitride (SiN x ), silicon oxide (SiO x ), indium tin oxide, indium zinc oxide or any combination thereof; an organic film comprising polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic-based resin (e.g., polymethyl methacrylate, polyacrylic acid, etc.), an epoxy-based resin (e.g., aliphatic glycidyl ether (AGE), etc.) or any combination thereof; or any combination of an inorganic film and an organic film.
[0475] Figure 3 is a schematic cross-sectional view showing an electronic device according to another embodiment.
[0476] Figure 3 Electronic devices can be used with Figure 2 The electronic device is different from the one of the embodiment in that at least the light shielding pattern 500 and the functional area 400 are further included on the packaging portion 300. The functional area 400 can be a color filter area, a color conversion area, or a combination of a color filter area and a color conversion area. Figure 4 The light-emitting device in the electronic device may be a series light-emitting device.
[0477] [ Figure 4 Description]
[0478] Figure 4 is a schematic perspective view of an electronic appliance 1 including a light emitting device according to the embodiment.
[0479] The electronic device 1 may be a device that displays a moving image or a still image, and may be not only a portable electronic device, such as a mobile phone, a smart phone, a tablet computer, a mobile communication terminal, an electronic notepad, an e-book, a portable multimedia player (PMP), a navigation device, or an ultra-mobile PC (UMPC), but may also be various products or components thereof, such as a television, a laptop computer, a monitor, a sign, or the Internet of Things (IoT). In an embodiment, the electronic device 1 may be a wearable device or a component thereof, such as a smart watch, a watch phone, a glasses-type display, or a head-mounted display (HMD). However, the embodiment is not limited thereto.
[0480] Examples of the electronic device 1 may include a vehicle dashboard, a vehicle center panel, a central information display arranged on the vehicle dashboard, a vehicle interior mirror display that replaces a side mirror, an entertainment display for a vehicle rear seat or a display arranged on the back of a front seat, a head-up display (HUD) mounted on the front of the vehicle or projected on the front windshield, or a computer-generated holographic augmented reality head-up display (CGH ARHUD). For ease of explanation, Figure 4 An embodiment is illustrated in which the electronic equipment 1 is a smartphone.
[0481] The electronic equipment 1 may include a display area DA and a non-display area NDA outside the display area DA. The display device may realize an image through a two-dimensional array of pixels arranged in the display area DA.
[0482] The non-display area NDA may be an area where no image is displayed and may surround (e.g., completely surround) the display area DA. A driver for supplying electrical signals or power to a display device arranged in the display area DA may be arranged in the non-display area NDA. A pad may be arranged in the non-display area NDA, the pad being an area to which electronic components or a printed circuit board can be electrically connected.
[0483] In the electronic device 1, the length in the x-axis direction and the length in the y-axis direction may be different from each other. Figure 4 , the length in the x-axis direction may be shorter than the length in the y-axis direction. In an embodiment, the length in the x-axis direction may be the same as the length in the y-axis direction. In an embodiment, the length in the x-axis direction may be longer than the length in the y-axis direction.
[0484] [ Figure 5 and Figures 6A to 6C Description]
[0485] Figure 5 is a schematic perspective view of the exterior of a vehicle 1000 as an electronic appliance including a light emitting device according to the embodiment. Figures 6A to 6C Each is a schematic diagram of the interior of a vehicle 1000 according to an embodiment.
[0486] refer to Figure 5 、 Figure 6A 、 Figure 6B and Figure 6C , embodiments of vehicle 1000 may include various devices for moving a transported object, such as a person, object, or animal, from a starting point to a destination. Examples of vehicle 1000 may include vehicles that travel on roads or tracks, ships that travel on the sea or on rivers, and airplanes that fly in the air using air.
[0487] Vehicle 1000 can travel on roads or tracks. Vehicle 1000 can move in selectable directions based on the rotation of at least one wheel. In embodiments, vehicle 1000 can include three-wheeled or four-wheeled vehicles, construction machinery, two-wheeled vehicles, prime movers, bicycles, and trains traveling on tracks.
[0488] Vehicle 1000 may include a main body of vehicle 1000 having an interior and an exterior, and a chassis, which is a portion other than the main body in which mechanical equipment necessary for driving is mounted. The exterior of vehicle 1000 may include a front panel, a bonnet, a roof panel, a rear panel, a trunk, and pillars provided at the boundaries between doors. The chassis of vehicle 1000 may include a power generation device, a power transmission device, a drive device, a steering device, a brake device, a suspension device, a transmission device, a fuel system, front and rear wheels, and left and right wheels.
[0489] The vehicle 1000 may include side windows 1100 , a front window 1200 , side mirrors 1300 , a cluster piece 1400 , a center panel 1500 , a passenger seat instrument panel 1600 , and a display device 2 .
[0490] The side window glass 1100 and the front window glass 1200 may be separated by pillars disposed between the side window glass 1100 and the front window glass 1200 .
[0491] Side window glass 1100 may be mounted on the side of vehicle 1000. In an embodiment, side window glass 1100 may be mounted on a door of vehicle 1000. Multiple side window glass 1100 may be provided and may face each other. In an embodiment, side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In an embodiment, first side window glass 1110 may be positioned adjacent to cluster member 1400, and second side window glass 1120 may be positioned adjacent to passenger seat instrument panel 1600.
[0492] In an embodiment, the side window glasses 1100 may be spaced apart from each other in the x-axis direction or the -x-axis direction. In an embodiment, the first side window glass 1110 and the second side window glass 1120 may be spaced apart from each other in the x-axis direction or the -x-axis direction. For example, the virtual straight line L connecting the side window glasses 1100 may extend in the x-axis direction or the -x-axis direction. In an embodiment, the virtual straight line L connecting the first side window glass 1110 and the second side window glass 1120 may extend in the x-axis direction or the -x-axis direction.
[0493] The front window glass 1200 may be installed at the front of the vehicle 1000. The front window glass 1200 may be disposed between the side window glasses 1100 facing each other.
[0494] The side-view mirror 1300 can provide a rear view of the vehicle 1000. The side-view mirror 1300 can be mounted on the exterior of the vehicle 1000. In an embodiment, a plurality of side-view mirrors 1300 can be provided. One of the side-view mirrors 1300 can be arranged outside the first side window glass 1110, and another of the side-view mirrors 1300 can be arranged outside the second side window glass 1120.
[0495] Cluster 1400 may be arranged in front of the steering wheel and may include a tachometer, a speedometer, a coolant temperature gauge, a fuel gauge, a turn signal indicator, a high beam indicator, warning lights, a seat belt warning light, an odometer, a driving recorder, an automatic transmission selector indicator light, a door open warning light, an engine oil warning light, and / or a low fuel warning light.
[0496] The center panel 1500 may include a control panel on which buttons for adjusting an audio device, an air conditioning device, and a seat heater are provided. The center panel 1500 may be arranged on a side of the cluster piece 1400 .
[0497] The passenger-seat instrument panel 1600 may be spaced apart from the cluster piece 1400, and the center panel 1500 may be disposed between the cluster piece 1400 and the passenger-seat instrument panel 1600. In an embodiment, the cluster piece 1400 may be disposed corresponding to a driver's seat (not shown), and the passenger-seat instrument panel 1600 may be disposed corresponding to a passenger seat (not shown). In an embodiment, the cluster piece 1400 may be adjacent to the first side window glass 1110, and the passenger-seat instrument panel 1600 may be adjacent to the second side window glass 1120.
[0498] In an embodiment, the display device 2 may include a display panel 3, and the display panel 3 may display an image. The display device 2 may be arranged inside the vehicle 1000. In an embodiment, the display device 2 may be arranged between the side window glasses 1100 facing each other. The display device 2 may be arranged on at least one of the cluster member 1400, the center panel 1500, and the passenger seat instrument panel 1600.
[0499] The display device 2 may include an organic light-emitting display device, an inorganic electroluminescent display device, a quantum dot display device, etc. Hereinafter, an organic light-emitting display device including a light-emitting device according to the embodiment will be described as an example of the display device 2. However, various types of the above-mentioned display devices may be used in the embodiment.
[0500] refer to Figure 6A , the display device 2 can be arranged on the central panel 1500. In an embodiment, the display device 2 can display navigation information. In an embodiment, the display device 2 can display information about audio settings, video settings, or vehicle settings.
[0501] refer to Figure 6B Display device 2 may be disposed on clusterware 1400. In an embodiment, clusterware 1400 may display driving information, etc., via display device 2. For example, clusterware 1400 may digitally display driving information, etc. Clusterware 1400 may digitally display vehicle information and driving information as images. In an embodiment, the needle and gauge of a tachometer, as well as various warning lights or icons, may be displayed via digital signals.
[0502] refer to Figure 6C , the display device 2 may be arranged on the passenger seat instrument panel 1600. The display device 2 may be embedded in the passenger seat instrument panel 1600 or arranged on the passenger seat instrument panel 1600. In an embodiment, the display device 2 arranged on the passenger seat instrument panel 1600 may display images related to the information displayed on the cluster piece 1400 and / or the information displayed on the center panel 1500. In an embodiment, the display device 2 arranged on the passenger seat instrument panel 1600 may display information different from the information displayed on the cluster piece 1400 and / or the information displayed on the center panel 1500.
[0503] [Manufacturing method]
[0504] The layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region can be formed in a selected region by using various methods (e.g., vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, laser induced thermal imaging, etc.).
[0505] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by vacuum deposition, the deposition temperature may be about 100° C. to about 500° C. ... -8 About 10 -3 Torr vacuum and about to about Deposition is carried out at a deposition rate of .
[0506] [Definition of terms]
[0507] As used herein, the term "C3-C 60 A "carbocyclic group" may be a cyclic group consisting only of carbon atoms as ring atoms and having three to sixty (e.g., 3 to 30, 3 to 20, 3 to 15, 3 to 8, or 3 to 6) carbon atoms, and the term "C1-C 60 The "heterocyclic group" may be a cyclic group having 1 to 60 (e.g., 1 to 30, 1 to 20, 1 to 15, 1 to 10, 1 to 8, or 1 to 6) carbon atoms and further having a heteroatom other than a carbon atom as a ring-constituting atom. 60 Carbocyclic groups and C1-C 60 The heterocyclic groups may each be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are fused to each other. 60 The number of ring atoms of the heterocyclic group can be 3 to 61 (e.g., 3 to 30, 3 to 20, 3 to 15, 3 to 8, or 3 to 6).
[0508] As used herein, the term "cyclic group" may be a C3-C 60 Carbocyclic group or C1-C 60 Heterocyclic group.
[0509] As used herein, the term "π-electron-rich C3-C 60 The "cyclic group" may be a cyclic group having three to sixty (e.g., 3 to 30, 3 to 20, 3 to 15, 3 to 8, or 3 to 6) carbon atoms and may not contain *-N=*' as a ring-forming portion, and the term "π-electron-deficient nitrogen-containing C1-C 60 The "cyclic group" may be a heterocyclic group having one to sixty (e.g., 1 to 30, 1 to 20, 1 to 15, 1 to 10, 1 to 8, or 1 to 6) carbon atoms and may contain *-N=*' as a ring-forming portion.
[0510] In an embodiment,
[0511] C3-C 60 The carbocyclic group may be a T1 group or a group in which two or more T1 groups are fused to each other (e.g., a cyclopentadiene group, an adamantane group, a norbornane group, a phenyl group, a pentalene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a phenanthrenyl group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, group, perylene group, pentaphenyl group, heptalene group, tetracene group, phenanthren group, hexacenyl group, pentacene group, rubride group, coronene group, ovaphenyl group, indene group, fluorene group, spiro-bifluorene group, benzofluorene group, indenophenanthrene group or indenoanthracene group),
[0512] C1-C 60 The heterocyclic group may be a T2 group, a group in which at least two T2 groups are fused to each other, or a group in which at least one T2 group and at least one T1 group are fused to each other (e.g., a pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzothiorrole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzothiorrole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofuranocarbazole group, a benzothiophenocarbazole group, a benzothiorrolecarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthothiorrole group, a benzofuranodibenzofuran group, a benzofuranodibenzothiophene group, a benzothiophene group, a benzothiophene group, a benzofuranodibenzofuran group, a benzofuranodibenzothiophene group, a benzothiophene group, a benzofuranodi ... dibenzothiophene group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, oxadiazole group, thiazole group, isothiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzisoxazole group, benzothiazole group, benzisothiazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzoquinolinyl group group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, etc.),
[0513] π-electron-rich C3-C 60The cyclic group may be a T1 group, a group in which two or more T1 groups are fused to each other, a T3 group, a group in which two or more T3 groups are fused to each other, or a group in which at least one T3 group and at least one T1 group are fused to each other (e.g., C3-C 60 carbocyclic group, 1H-pyrrole group, thiole group, borole group, 2H-pyrrole group, 3H-pyrrole group, thiophene group, furan group, indole group, benzindole group, naphthoindole group, isoindole group, benzisoindole group, naphthoisoindole group, benzothiole group, benzothiophene group, benzofuran group, carbazole group, dibenzothiole group, dibenzothiophene group, dibenzofuran group, indenocarbazole group, indolocarbazole group, benzofuranocarbazole group, benzothienocarbazole group, benzothioleocarbazole group, benzoindolocarbazole group, benzocarbazole group, benzonaphthofuran group, benzonaphthothiophene group, benzonaphthothiole group, benzofuranodibenzofuran group, benzofuranodibenzothiophene group, benzothienodibenzothiophene group, etc.),
[0514] π-electron-deficient nitrogen-containing C1-C 60 The cyclic group may be a T4 group, a group in which at least two T4 groups are fused to each other, a group in which at least one T4 group and at least one T1 group are fused to each other, a group in which at least one T4 group and at least one T3 group are fused to each other, or a group in which at least one T4 group, at least one T1 group, and at least one T3 group are fused to each other (e.g., a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzisoxazole group, group, benzothiazole group, benzisothiazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group, benzoisoquinoline group, quinoxaline group, benzoquinoxaline group, quinazoline group, benzoquinazoline group, phenanthroline group, cinnoline group, phthalazine group, naphthyridine group, imidazopyridine group, imidazopyrimidine group, imidazotriazine group, imidazopyrazine group, imidazopyridazine group, azacarbazole group, azafluorene group, azadibenzosilole group, azadibenzothiophene group, azadibenzofuran group, etc.),
[0515] wherein the T1 group can be a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclobutene group, a cyclopentene group, a cyclopentadiene group, a cyclohexene group, a cyclohexadiene group, a cycloheptene group, an adamantane group, a norbornane (or bicyclo[2.2.1]heptane) group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group or a phenyl group,
[0516] The T2 group can be a furan group, a thiophene group, a 1H-pyrrole group, a thiol group, a borolide group, a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azathiol group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a tetrazine group, a pyrrolidine group, an imidazolidinyl group, a dihydropyrrole group, a piperidine group, a tetrahydropyridine group, a dihydropyridine group, a hexahydropyrimidine group, a tetrahydropyrimidine group, a dihydropyrimidine group, a piperazine group, a tetrahydropyrazine group, a dihydropyrazine group, a tetrahydropyridazine group or a dihydropyridazine group,
[0517] The T3 group may be a furan group, a thiophene group, a 1H-pyrrole group, a thiol group or a borole group, and
[0518] The T4 group can be a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azathiazole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group or a tetrazine group.
[0519] As used herein, the terms "cyclic group", "C3-C 60 Carbocyclic group", "C1-C 60 Heterocyclic groups", "π-electron-rich C3-C 60 Cyclic group" or "π-electron-deficient nitrogen-containing C1-C 60 The “cyclic group” may be a group condensed with any cyclic group, a monovalent group, or a polyvalent group (e.g., a divalent group, a trivalent group, a tetravalent group, etc.) according to the structure of the formula using the corresponding term. For example, a “phenyl group” may be a benzo group, a phenyl group, a phenylene group, etc., which can be easily understood by those skilled in the art based on the structure of the formula including the “phenyl group”.
[0520] Unit price C3-C 60 Carbocyclic groups and monovalent C1-C 60Examples of heterocyclic groups may include C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups and monovalent non-aromatic fused heteropolycyclic groups, and divalent C3-C 60 Carbocyclic groups and divalent C1-C 60 Examples of heterocyclic groups may include C3-C 10 Cycloalkylene groups, C1-C 10 Heterocycloalkylene group, C3-C 10 Cycloalkenylene group, C1-C 10 Heterocycloalkenylene group, C6-C 60 Arylene group, C1-C 60 heteroarylene group, a divalent non-aromatic fused polycyclic group, and a divalent non-aromatic fused heteropolycyclic group.
[0521] As used herein, the term "C1-C 60 The “alkyl group” may be a linear or branched monovalent aliphatic hydrocarbon group having 1 to 60 (e.g., 1 to 30, 1 to 20, 1 to 15, 1 to 10, 1 to 8, or 1 to 6) carbon atoms, and examples thereof may include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, an alkyl group, an alkyl group, an alkyl group, an alkyl group, an alkyl group, an alkyl group, an alkyl group, an alkyl group, an alkyl group, an alkyl group, an alkyl group, an alkyl group, an alkyl group As used herein, the term "C1-C2" refers to a group comprising: a tert-hexyl group, a secondary pentyl group, a tert-pentyl group, a secondary isopentyl group, a n-hexyl group, an isohexyl group, a secondary hexyl group, a tert-hexyl group, a n-heptyl group, an isoheptyl group, a secondary heptyl group, a tert-heptyl group, a n-octyl group, an isooctyl group, a secondary octyl group, a tert-octyl group, a n-nonyl group, an isononyl group, a secondary nonyl group, a tert-nonyl group, a n-decyl group, an isodecyl group, a secondary decyl group, and a tert-decyl group. 60 The "alkylene group" may be a C1-C 60 A divalent group of the same structure as an alkyl group.
[0522] As used herein, the term "C2-C 60 The "alkenyl group" may be a C2-C 60 The term "C2-C4" as used herein refers to a monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminal of the alkyl group, and examples thereof may include a vinyl group, a propenyl group, a butenyl group, and the like. 60The "alkenylene group" may be a 60 Alkenyl groups are divalent groups of the same structure.
[0523] As used herein, the term "C2-C 60 The "alkynyl group" may be a C2-C 60 The term "C2-C 2-alkyl" as used herein refers to a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the terminal of the alkyl group, and examples thereof may include an ethynyl group, a propynyl group, and the like. 60 The "alkynylene group" may be a 60 Alkynyl groups are divalent groups of the same structure.
[0524] As used herein, the term "C1-C 60 The "alkoxy group" may be -O(A 101 )(where A 101 Can be C1-C 60 An alkyl group) and examples thereof may include a methoxy group, an ethoxy group, an isopropoxy group and the like.
[0525] As used herein, the term "C3-C 10 The “cycloalkyl group” may be a monovalent saturated hydrocarbon cyclic group having 3 to 10 (e.g., 3, 4, 5, 6, 7, 8, 9, or 10) carbon atoms, and examples thereof may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group (or a bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, and the like. As used herein, the term “C3-C 10 The cycloalkylene group may be a group having a C3-C 10 A divalent group of the same structure as the cycloalkyl group.
[0526] As used herein, the term "C1-C 10 The “heterocycloalkyl group” may be a monovalent cyclic group having 1 to 10 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10) carbon atoms further containing at least one heteroatom other than carbon atoms as a ring-constituting atom, and examples thereof may include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, a tetrahydrothienyl group, and the like. As used herein, the term “C1-C 10 The "heterocycloalkylene group" may be a 10 Heterocycloalkyl groups are divalent groups of the same structure.
[0527] As used herein, the term "C3-C 10 The term "cycloalkenyl group" as used herein may be a monovalent cyclic group having 3 to 10 (e.g., 3, 4, 5, 6, 7, 8, 9, or 10) carbon atoms, at least one carbon-carbon double bond, and no aromaticity in its cyclic structure, and examples thereof may include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, and the like. As used herein, the term "C3-C 10 The cycloalkenylene group may be a 10 A cycloalkenyl group is a divalent group of the same structure.
[0528] As used herein, the term "C1-C 10 The "heterocycloalkenyl group" may be a monovalent cyclic group having 1 to 10 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10) carbon atoms, further containing at least one heteroatom other than carbon atoms as a ring-forming atom and at least one double bond in its cyclic structure. 10 Examples of heterocycloalkenyl groups may include 4,5-dihydro-1,2,3,4-oxatriazolyl groups, 2,3-dihydrofuranyl groups, 2,3-dihydrothienyl groups, and the like. As used herein, the term "C1-C 10 The "heterocycloalkenylene group" may be a 10 Heterocycloalkenyl group is a divalent group of the same structure.
[0529] As used herein, the term "C6-C 60 An "aryl group" may be a monovalent group having a carbocyclic aromatic system containing six to sixty (e.g., 6 to 30, 6 to 20, 6 to 15, or 6 to 10) carbon atoms, and the term "C6-C 60 The "arylene group" may be a divalent group having a carbocyclic aromatic system containing 6 to 60 (e.g., 6 to 30, 6 to 20, 6 to 15, or 6 to 10) carbon atoms. 60 Examples of the aryl group may include a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, phenyl group, peryl group, pentaphenyl group, heptaphenyl group, tetraphenyl group, peryl group, hexyl group, pentacene group, rubinyl group, coronenyl group, ovophenyl group, etc. 60 Aryl groups and C6-C 60 When the arylene groups each contain two or more rings, the corresponding two or more rings may be fused to each other.
[0530] As used herein, the term "C1-C 60 The "heteroaryl group" may be a monovalent group having a heterocyclic aromatic system having 1 to 60 (e.g., 1 to 30, 1 to 20, 1 to 15, 1 to 10, 1 to 8, or 1 to 6) carbon atoms further containing at least one heteroatom other than carbon atoms as a ring-forming atom. As used herein, the term "C1-C 60 The "heteroarylene group" may be a divalent group having a heterocyclic aromatic system having 1 to 60 (e.g., 1 to 30, 1 to 20, 1 to 15, 1 to 10, 1 to 8, or 1 to 6) carbon atoms further containing at least one heteroatom other than carbon atoms as a ring-forming atom. C1-C 60 Examples of heteroaryl groups may include pyridyl groups, pyrimidinyl groups, pyrazinyl groups, pyridazinyl groups, triazinyl groups, quinolyl groups, benzoquinolyl groups, isoquinolyl groups, benzoisoquinolyl groups, quinoxalinyl groups, benzoquinoxalinyl groups, quinazolinyl groups, benzoquinazolinyl groups, cinnolinyl groups, phenanthrolinyl groups, phthalazinyl groups, naphthyridinyl groups, and the like. 60 Heteroaryl groups and C1-C 60 When the heteroarylene groups each contain two or more rings, the corresponding two or more rings may be fused to each other.
[0531] As used herein, the term "monovalent non-aromatic fused polycyclic group" may be a monovalent group (e.g., having 8 to 60 (e.g., 8 to 30, 8 to 20, 8 to 15, or 8 to 10) carbon atoms) having two or more rings fused to each other, only carbon atoms as ring atoms, and no aromaticity in the entire molecular structure. Examples of monovalent non-aromatic fused polycyclic groups may include indenyl groups, fluorenyl groups, spiro-bifluorenyl groups, benzofluorenyl groups, indenophenanthryl groups, indenoanthryl groups, and the like. As used herein, the term "divalent non-aromatic fused polycyclic group" may be a divalent group having the same structure as the monovalent non-aromatic fused polycyclic group described above.
[0532] The term “monovalent non-aromatic hetero-condensed polycyclic group” as used herein may be a monovalent group (for example, having 1 to 60 (for example, 1 to 30, 1 to 20, 1 to 15, 1 to 10, 1 to 8, or 1 to 6) carbon atoms) having two or more rings fused to each other, further containing at least one heteroatom other than a carbon atom as a ring-constituting atom and not having aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic hetero-condensed polycyclic group may include a pyrrolyl group, a thienyl group, a furyl group, an indolyl group, a benzindolyl group, a naphthoindolyl group, an isoindolyl group, a benzisoindolyl group, a naphthoisoindolyl group, a benzothiorolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzothiorolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzothiorolyl group, an azadibenzothiophenyl group, an azadibenzofuranyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group
[0045] The present invention also includes but is not limited to: a benzothiazolyl group, a benzopyrazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzoxadiazolyl group, a benzothiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazotriazinyl group, an imidazopyrazinyl group, an imidazopyridazinyl group, an indenocarbazolyl group, an indolocarbazolyl group, a benzofuranocarbazolyl group, a benzothienocarbazolyl group, a benzothiorrolocarbazolyl group, a benzoindolocarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a benzonaphthothiophenyl group, a benzofuranodibenzofuranyl group, a benzofuranodibenzothiophenyl group, and a benzothienodibenzothiophenyl group. The term "divalent non-aromatic condensed heteropolycyclic group" as used herein may be a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
[0533] As used herein, the term "C6-C 60 The "aryloxy group" may be -O(A 102 )(where A 102 Can be C6-C 60 aryl group), and as used herein, the term "C6-C 60 The "arylthio group" may be a -S(A 103 )(where A 103 Can be C6-C 60 A group represented by an aryl group).
[0534] As used herein, the term "C7-C 60 The "arylalkyl group" may be composed of -(A104 )(A 105 )(where A 104 Can be C1-C 54 an alkylene group, and A 105 Can be C6-C 59 aryl group), and as used herein, the term "C2-C 60 A "heteroarylalkyl group" may be composed of -(A 106 )(A 107 )(where A 106 Can be C1-C 59 an alkylene group, and A 107 Can be C1-C 59 A group represented by a heteroaryl group).
[0535] In the specification, the term "R 10a ” can be:
[0536] deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, or a nitro group;
[0537] Each unsubstituted or deuterated, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, C2-C 60 Heteroarylalkyl group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 ),-C(=O)(Q 11 )、-S(=O)2(Q 11 ),-P(=O)(Q 11 )(Q 12 ) or any combination thereof substituted C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group or C1-C 60 alkoxy groups;
[0538] Each unsubstituted or deuterated, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 60 Alkyl groups, C2-C60 Alkenyl groups, C2-C 60 Alkynyl group, C1-C 60 Alkoxy groups, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, C2-C 60 Heteroarylalkyl group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 ),-C(=O)(Q 21 )、-S(=O)2(Q 21 ),-P(=O)(Q 21 )(Q 22 ) or any combination thereof substituted C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, or C2-C 60 a heteroarylalkyl group; or
[0539] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 ),-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ).
[0540] In this specification, groups Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; each unsubstituted or substituted by deuterium, -F, a cyano group, a C1-C 60Alkyl groups, C1-C 60 C1-C12 substituted by an alkoxy group, a phenyl group, a biphenyl group or any combination thereof 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group, C1-C 60 Alkoxy groups, C3-C 60 Carbocyclic group or C1-C 60 Heterocyclic group; C7-C 60 Arylalkyl group; or C2-C 60 Heteroarylalkyl group.
[0541] As used herein, the term "heteroatom" may be any atom other than a carbon atom or a hydrogen atom. Examples of heteroatoms may include O, S, N, P, Si, B, Ge, Se, and any combination thereof, wherein the number of heteroatoms may be 1 to 15, 1 to 10, 1 to 5, or 1 to 3, such as 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.
[0542] The term "transition metal" as used herein may include Hf, Ta, W, Re, Os, Ir, Pt, Au, and the like.
[0543] In the specification, the term "Ph" refers to a phenyl group, the term "Me" refers to a methyl group, the term "Et" refers to an ethyl group, the term "tert-Bu" or "Bu t ” each refers to a tert-butyl group, and the term “OMe” refers to a methoxy group.
[0544] As used herein, the term "biphenyl group" may be a "phenyl group substituted by a phenyl group". For example, a "biphenyl group" may be a C6-C 60 Aryl groups are substituted phenyl groups as substituents.
[0545] The term "terphenyl group" as used herein may be a "phenyl group substituted by a biphenyl group". For example, a "terphenyl group" may be a phenyl group substituted by a C6-C 60 C6-C substituted with aryl groups 60 Aryl groups are substituted phenyl groups as substituents.
[0546] Unless otherwise defined, the symbols * and *' as used herein each refer to a binding site to the adjacent atom in the corresponding formula or moiety.
[0547] In the specification, the terms "x-axis", "y-axis", and "z-axis" are not limited to the three axes in a rectangular coordinate system (e.g., a Cartesian coordinate system), and can be interpreted in a broader sense than the three axes in the aforementioned rectangular coordinate system. For example, the x-axis, y-axis, and z-axis can describe axes that are orthogonal to each other, or can describe axes in different directions that are not orthogonal to each other.
[0548] Hereinafter, the compound according to the embodiment and the light-emitting device according to the embodiment will be described in detail with reference to the following synthesis examples and examples. The phrase "using B instead of A" used to describe the synthesis examples means using an equimolar equivalent of B instead of A.
[0549] [Synthesis Examples and Examples]
[0550] The method of synthesizing the compound according to the embodiment will be described by exemplifying the synthesis methods of Compound 1, Compound 12, Compound 21, Compound 34, Compound 51, and Compound 63. The synthesis methods of the compounds described below are merely examples, and the synthesis methods of the compounds according to the embodiment are not limited thereto.
[0551] [Synthesis Example 1: Synthesis of Compound 1]
[0552]
[0553] Synthesis of intermediate 1-1
[0554] 1-Bromo-3-(triphenylsilyl)benzene (CAS No.: 185626-73-7) and 9H-carbazole (CAS No.: 86-74-8) were reacted in the presence of a Pd catalyst to obtain Intermediate 1-1. Intermediate 1-1 was identified by LC-MS.
[0555] C 36 H 27 NSi M+1:502.19
[0556] Synthesis of intermediate 1-2
[0557] Intermediate 1-1 was reacted with N-bromosuccinimide (CAS No. 128-08-5) to obtain Intermediate 1-2. Intermediate 1-2 was identified by LC-MS.
[0558] C 36 H 26 BrNSi M+1: 582.11
[0559] Synthesis of intermediates 1-3
[0560] 1-Bromo-2-fluorobenzene (CAS No. 1072-85-1) and 9H-carbazole (CAS No. 86-74-8) were reacted in the presence of K 3 PO 4 and DMF solvent to obtain Intermediate 1-3. Intermediate 1-3 was identified by LC-MS.
[0561] C 18 H 12 BrN M+1: 323.01
[0562] Synthesis of intermediates 1-4
[0563] After reacting Intermediate 1-3 with n-BuLi, trimethyl borate (CAS No. 121-43-7) was added thereto, and the reaction product was stirred at room temperature overnight, and H 2 O was added thereto to obtain Intermediate 1-4. Intermediate 1-4 was identified by LC-MS.
[0564] C 18 H 14 BNO2 M+1:288.12
[0565] Synthesis of intermediates 1-5
[0566] Intermediate 1-4 was reacted with 3-bromocarbazole (CAS No. 1592-95-6) in the presence of a Pd catalyst to obtain Intermediate 1-5. Intermediate 1-5 was identified by LC-MS.
[0567] C 30 H 20 N2 M+1: 409.17
[0568] Synthesis of compound 1
[0569] 3.0 g of intermediate 1-2, 2.1 g of intermediate 1-5, 0.19 g of Pd2(dba)3, 0.17 mL of P( t Bu)3 (50 wt.%, in xylene), 1.49 g NaO t Bu and 26mL toluene were added to RBF, and the mixture was stirred at 120°C overnight. After the reaction was complete, an extraction process was performed using ethyl acetate, and the organic layer collected therefrom was dried using magnesium sulfate. The residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography to obtain 3.3g (yield: 71%) of compound 1. Compound 1 was identified by LC-MS.
[0570] C 66 H 45 N3Si M+1:908.34
[0571] [Synthesis Example 2: Synthesis of Compound 12]
[0572]
[0573] Synthesis of intermediate 12-1
[0574] 3-Bromo-1,1′-biphenyl (CAS No. 2113-57-7) and 9H-carbazole (CAS No. 86-74-8) were reacted in the presence of a Pd catalyst to obtain Intermediate 12-1. Intermediate 12-1 was identified by LC-MS.
[0575] C 24 H 17 N M+1:320.15
[0576] Synthesis of intermediate 12-2
[0577] Intermediate 12-1 was reacted with N-bromosuccinimide (CAS No. 128-08-5) to obtain Intermediate 12-2, which was identified by LC-MS.
[0578] C 24 H 16 BrN M+1: 398.17
[0579] Synthesis of compound 12
[0580] 2.8 g of intermediate 12-2, 2.87 g of intermediate 1-5, 0.26 g of Pd2(dba)3, 0.23 mL of P( t Bu)3 (50 wt.%, in xylene), 2.03 g NaO t Bu and 35mL toluene were added to RBF, and the mixture was stirred at 120 ° C overnight. After the reaction was completed, an extraction process was performed using ethyl acetate, and the organic layer collected therefrom was dried using magnesium sulfate. The residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography to obtain 3.65g (yield: 72%) of compound 12. Compound 12 was identified by LC-MS.
[0581] C 54 H 35 N3 M+1:726.29
[0582] [Synthesis Example 3: Synthesis of Compound 21]
[0583]
[0584] Synthesis of Intermediate 21-1
[0585] Phenylboronic acid (CAS No. 98-80-6) and 9H-carbazole (CAS No. 86-74-8) were reacted in the presence of a Pd catalyst to obtain Intermediate 21-1. Intermediate 21-1 was identified by LC-MS.
[0586] C 18 H 13 N M+1:244.11
[0587] Synthesis of Intermediate 21-2
[0588] Intermediate 21-1 was reacted with N-bromosuccinimide (CAS No. 128-08-5) to obtain Intermediate 21-2, which was identified by LC-MS.
[0589] C 18 H 12 BrN M+1: 323.01
[0590] Synthesis of Intermediate 21-3
[0591] 1-Bromo-2-fluorobenzene (CAS No. 1072-85-1) and 9H-carbazole (CAS No. 86-74-8) were reacted with stirring at 100° C. in the presence of K 3 PO 4 overnight to obtain Intermediate 21-3. Intermediate 21-3 was identified by LC-MS.
[0592] C 18 H 12 BrN M+1: 323.01
[0593] Synthesis of Intermediate 21-4
[0594] After reacting Intermediate 21-3 with n-BuLi, trimethyl borate (CAS#: 121-43-7) was added thereto, and the reaction product was stirred at room temperature overnight, and H 2 O was added thereto to obtain Intermediate 21-4. Intermediate 21-4 was identified by LC-MS.
[0595] C 18 H 14 BNO2 M+1:288.12
[0596] Synthesis of Intermediate 21-5
[0597] Intermediate 21-4 was reacted with 2-bromocarbazole (CAS No. 3652-90-2) in the presence of a Pd catalyst to obtain Intermediate 21-5. Intermediate 21-5 was identified by LC-MS.
[0598] C 30 H 20N2 M+1: 409.16
[0599] Synthesis of compound 21
[0600] 2.5 g of intermediate 21-2, 3.17 g of intermediate 21-5, 0.28 g of Pd2(dba)3, 0.25 mL of P( t Bu)3 (50 wt.%, in xylene), 2.24 g NaO t Bu and 38mL toluene were added to RBF, and the mixture was stirred at 120°C overnight. After the reaction was complete, an extraction process was performed using ethyl acetate, and the organic layer collected therefrom was dried using magnesium sulfate. The residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography to obtain 3.4g (yield: 67%) of compound 21. Compound 21 was identified by LC-MS.
[0601] C 48 H 31 N3 M+1:650.26
[0602] [Synthesis Example 4: Synthesis of Compound 34]
[0603]
[0604] Synthesis of Intermediate 34-1
[0605] (4-Bromophenyl)triphenylsilane (CAS No. 18737-40-1) and bis(pinacolato)diboron (CAS No. 73183-34-3) were reacted in the presence of a Pd catalyst to obtain Intermediate 34-1. Intermediate 34-1 was identified by LC-MS.
[0606] C 30 H 31 BO2Si M+1:463.23
[0607] Synthesis of intermediate 34-2
[0608] Intermediate 34-1 was reacted with 1-iodo-2-nitrobenzene (CAS No. 609-73-4) in the presence of a Pd catalyst to obtain Intermediate 34-2. Intermediate 34-2 was identified by LC-MS.
[0609] C 30 H 23 NO2Si M+1:458.16
[0610] Synthesis of intermediate 34-3
[0611] Intermediate 34-2 was reacted with triphenylphosphine (CAS No. 603-35-0) to obtain Intermediate 34-3. Intermediate 34-3 was identified by LC-MS.
[0612] C 30 H 23 NSi M+1:426.17
[0613] Synthesis of intermediate 34-4
[0614] Intermediate 34-3 and 1-bromo-2-fluorobenzene (CAS No. 1072-85-1) were reacted at 100° C. in the presence of K 3 PO 4 with stirring overnight to obtain Intermediate 34-4. Intermediate 34-4 was identified by LC-MS.
[0615] C 36 H 26 BrNSi M+1: 582.10
[0616] Synthesis of intermediate 34-5
[0617] After reacting Intermediate 34-4 with n-BuLi, trimethyl borate (CAS No. 121-43-7) was added thereto, and the reaction product was stirred at room temperature overnight, and H 2 O was added thereto to obtain Intermediate 34-5. Intermediate 34-5 was identified by LC-MS.
[0618] C 36 H 28 BNO2Si M+1:546.20
[0619] Synthesis of Intermediate 34-6
[0620] Intermediate 34-5 was reacted with 3-bromocarbazole (CAS No. 1592-95-6) in the presence of a Pd catalyst to obtain Intermediate 34-6. Intermediate 34-6 was identified by LC-MS.
[0621] C 48 H 34 N2Si M+1:667.25
[0622] Synthesis of Intermediate 34-7
[0623] 4-Bromobiphenyl (CAS No. 92-66-0) and 9H-carbazole (CAS No. 86-74-8) were reacted in the presence of a Pd catalyst to obtain Intermediate 34-7, which was identified by LC-MS.
[0624] C 24 H 17 N M+1:320.14
[0625] Synthesis of Intermediate 34-8
[0626] Intermediate 34-7 was reacted with N-bromosuccinimide (CAS No. 128-08-5) to obtain Intermediate 34-8. Intermediate 34-8 was identified by LC-MS.
[0627] C 24 H 16 BrN M+1: 399.04
[0628] Synthesis of compound 34
[0629] 2.0 g of intermediate 34-8, 3.35 g of intermediate 34-6, 0.18 g of Pd2(dba)3, 0.16 mL of P( t Bu)3 (50 wt.%, in xylene), 1.45 g NaO t Bu and 25mL toluene were added to RBF, and the mixture was stirred at 120°C overnight. After the reaction was complete, an extraction process was performed using ethyl acetate, and the organic layer collected therefrom was dried using magnesium sulfate. The residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography to obtain 3.2g (yield: 66%) of compound 34. Compound 34 was identified by LC-MS.
[0630] C 72 H 49 N3Si M+1:985.38
[0631] [Synthesis Example 5: Synthesis of Compound 51]
[0632]
[0633] Synthesis of Intermediate 51-1
[0634] 2-Bromocarbazole (CAS No. 3652-90-2) and p-toluenesulfonyl chloride (CAS No. 98-59-9) were reacted to obtain Intermediate 51-1, which was identified by LC-MS.
[0635] C 19 H 14 BrNO2S M+1:401.99
[0636] Synthesis of Intermediate 51-2
[0637] Intermediate 51-1 and Intermediate 1-5 were reacted in the presence of a Pd catalyst to obtain Intermediate 51-2. Intermediate 51-2 was identified by LC-MS.
[0638] C 49 H 33 N3O2S M+1:729.24
[0639] Synthesis of Intermediate 51-3
[0640] Intermediate 51-2 was reacted with tetrabutylammonium fluoride (CAS No. 429-41-4) to obtain Intermediate 51-3, which was identified by LC-MS.
[0641] C 42 H 27 N3 M+1:575.23
[0642] Synthesis of compound 51
[0643] 2.0 g 1-bromo-3-(triphenylsilyl)benzene (CAS No.: 185626-73-7), 2.76 g intermediate 51-3, 0.18 g Pd2(dba)3, 0.16 mL P( t Bu)3 (50 wt.%, in xylene), 1.45 g NaO t Bu and 24mL toluene were added to RBF, and the mixture was stirred at 120°C overnight. After the reaction was complete, an extraction process was performed using ethyl acetate, and the organic layer collected therefrom was dried using magnesium sulfate. The residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography to obtain 3.2g (yield: 73%) of compound 51. Compound 51 was identified by LC-MS.
[0644] C 66 H 45 N3Si M+1:909.34
[0645] [Synthesis Example 6: Synthesis of Compound 63]
[0646]
[0647] Synthesis of Intermediate 63-1
[0648] After reacting 3-bromo-1,1'-biphenyl (CAS No. 2113-57-7) and n-BuLi, trimethyl borate (CAS No. 121-43-7) was added, and the reaction product was stirred at room temperature overnight. H2O was added to obtain Intermediate 63-1. Intermediate 63-1 was identified by LC-MS.
[0649] C 12 H 11 BO2 M+1:199.09
[0650] Synthesis of Intermediate 63-2
[0651] Intermediate 63-1 was reacted with 1-bromo-3-fluorobenzene (CAS No. 1073-06-9) in the presence of a Pd catalyst to obtain Intermediate 63-2. Intermediate 63-2 was identified by LC-MS.
[0652] C 18 H 13 F M+1:249.1
[0653] Synthesis of Intermediate 63-3
[0654] Intermediate 63-2 and 2-bromocarbazole (CAS No. 3652-90-2) were reacted at 100° C. in the presence of K 3 PO 4 with stirring overnight to obtain Intermediate 63-3. Intermediate 63-3 was identified by LC-MS.
[0655] C 30 H 20 BrN M+1:476.08
[0656] Synthesis of compound 63
[0657] 2.5 g of intermediate 63-3, 2.15 g of intermediate 1-5, 0.19 g of Pd2(dba)3, 0.17 mL of P( t Bu)3 (50 wt.%, in xylene), 1.52 g NaO t Bu and 26mL toluene are added to RBF, and the mixture is stirred at 120 ℃ and spend the night.After the reaction is completed, an extraction process is carried out using ethyl acetate, and the organic layer collected therefrom is dried using magnesium sulfate. The residue obtained by evaporating the solvent is separated and purified by silica gel column chromatography to obtain 3.0g (yield: 71%) of compound 63. Compound 63 is identified by LC-MS.
[0658] C 60 H 39 N3 M+1: 802.31
[0659] [Example 1]
[0660] Corning 15Ω / cm 2 The ITO glass substrate was cut into a size of 50 mm×50 mm×0.5 mm, ultrasonicated with isopropyl alcohol and pure water for 5 minutes each, and cleaned by exposing to ultraviolet rays and ozone for 30 minutes.The ITO glass substrate was provided to a vacuum deposition apparatus.
[0661] On an ITO glass substrate, HAT-CN was deposited to form A hole injection layer having a thickness of 1000 nm was formed, and a hole transport layer was formed on the hole injection layer, wherein BCFN as a first hole transport material was vacuum deposited onto the hole injection layer. and then vacuum depositing SiCzCz as a second hole transport material thereon to a thickness of thickness.
[0662] On the hole transport layer, compound 1 and SiTrzCz2 as the host and PtON-TBBI as the phosphorescent dopant were co-deposited in a weight ratio of 60:27:13 to form a hole transport layer having The thickness of the emission layer.
[0663] In having An electron transport layer is formed on the emission layer having a thickness of A first electron transport layer having a thickness of , and mSiTrz and LiQ are co-deposited thereon in a weight ratio of 1:1 to form a second electron transport layer. Alkali metal halide LiF is deposited on the electron transport layer to form a An electron injection layer of a thickness of 1000 nm was formed, and Al was vacuum-deposited on the electron injection layer to A thickness of , thereby forming a LiF / Al electrode, thereby manufacturing a light-emitting device.
[0664] The material used in the above-mentioned light-emitting device can be represented by the following formula.
[0665]
[0666] [Examples 2 to 6 and Comparative Examples 1 to 5]
[0667] Light-emitting devices were manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 were used instead of Compound 1 to form the emission layer.
[0668] [Evaluation Example 1]
[0669] In order to evaluate the characteristics of the light emitting devices of Examples 1 to 6 and Comparative Examples 1 to 5, the 2The driving voltage, current density and maximum quantum efficiency at the current density of 200 nm were measured. The driving voltage and current density of the light-emitting device were measured using a source meter (Keithley Instrument Inc., 2400 series), and the maximum quantum efficiency was measured by using an external quantum efficiency measurement device C9920-2-12 of Hamamatsu Photonics Inc. In evaluating the maximum quantum efficiency, brightness / current density was measured by using a luminance meter with calibrated wavelength sensitivity, and the maximum quantum efficiency was converted by assuming that an angular brightness distribution (Lambertian) of a completely reflecting diffuser was introduced. The evaluation results of the properties of the light-emitting device are shown in Table 1.
[0670] [Table 1]
[0671]
[0672]
[0673] Referring to the results of Table 1, it was confirmed that the light-emitting devices of Examples 1 to 6 had low driving voltages and excellent maximum quantum efficiencies compared to the light-emitting devices of Comparative Examples 1 to 5.
[0674] According to the embodiment, when the heterocyclic compound provided herein is used, a light-emitting device having reduced driving voltage and improved efficiency characteristics and a high-quality electronic device including the light-emitting device may be manufactured.
[0675] Embodiments have been disclosed herein, and although terms are used, they are used and to be interpreted in a generic and descriptive sense only and not for purposes of limitation. In some cases, as will be apparent to one of ordinary skill in the art, features, characteristics, and / or elements described with respect to an embodiment may be used alone or in combination with features, characteristics, and / or elements described with respect to other embodiments, unless specifically noted otherwise. Accordingly, one of ordinary skill in the art will understand that various changes in form and detail may be made without departing from the spirit and scope of the present disclosure.
Claims
1. A light-emitting device comprising: a first electrode; a second electrode facing the first electrode; an intermediate layer between the first electrode and the second electrode and including an emission layer; as well as Heterocyclic compound represented by Formula 1: [Formula 1] [Formula 2] In formula 1 and formula 2, b1, b6 and b7 are each independently an integer from 0 to 3, b5 is an integer from 0 to 4, Ar1, R1, R 21 to R 24 、R 31 to R 34 and R 41 to R 44 Each is independently a group represented by Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted by at least one R 10a Substituted C6-C 60 Aryloxy groups, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Arylthio group, unsubstituted or substituted with at least one R 10a Substituted C7-C 60 Arylalkyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 heteroarylalkyl group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(═O)(Q1), -S(═O)2(Q1), or -P(═O)(Q1)(Q2), R 31 to R 34 and R 41 to R 44 At least one of them is independently a group represented by Formula 2, Ar2, Ar3 and R5 to R7 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted by at least one R 10a Substituted C6-C 60 Aryloxy groups, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Arylthio group, unsubstituted or substituted with at least one R 10a Substituted C7-C 60 Arylalkyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 heteroarylalkyl group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(═O)(Q1), -S(═O)2(Q1), or -P(═O)(Q1)(Q2), R1, R 21 to R 24 、R 31 to R 34 、R 41 to R 44 and two or more of R5 to R7 are optionally bonded together to form an unsubstituted or substituted group. 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, L1 to L3 are each independently a single bond, unsubstituted or replaced by at least one R 10a Substituted divalent C3-C 60 Carbocyclic groups, either unsubstituted or substituted with at least one R 10a Substituted divalent C1-C 60 Heterocyclic groups, a1 to a3 are each independently an integer from 1 to 5, R 10a yes: deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, or a nitro group; Each unsubstituted or deuterated, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, C2-C 60 Heteroarylalkyl group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 ),-C(=O)(Q 11 )、-S(=O)2(Q 11 ),-P(=O)(Q 11 )(Q 12 ) or a combination thereof substituted C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group or C1-C 60 alkoxy groups; Each unsubstituted or deuterated, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group, C1-C 60 Alkoxy groups, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, C2-C 60 Heteroarylalkyl group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 ),-C(=O)(Q 21 )、-S(=O)2(Q 21 ),-P(=O)(Q 21 )(Q 22 ) or a combination thereof substituted C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group or C2-C 60 a heteroarylalkyl group; or -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 Each independently is: Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group or C1-C 60 an alkoxy group; or Each unsubstituted or deuterated, -F, cyano group, C1-C 60 Alkyl groups, C1-C 60 C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C7-C 60 Arylalkyl group or C2-C 60 heteroarylalkyl groups, and * indicates the binding site with the adjacent atom. The light-emitting device of claim 1 , wherein the emission layer comprises the heterocyclic compound.
3. The light emitting device according to claim 1, wherein The emissive layer comprises a host and a dopant, and The host includes the heterocyclic compound. The light-emitting device according to claim 1 , wherein the light-emitting device has a triplet energy level greater than or equal to 2.75 eV.
5. The light emitting device of claim 1 , wherein the light emitting device further comprises at least one of the following: a first covering layer outside the first electrode; and a second covering layer outside the second electrode, wherein At least one of the first cover layer and the second cover layer contains the heterocyclic compound.
6. An electronic device comprising the light emitting device according to any one of claims 1 to 5.
7. The electronic device of claim 6, wherein the electronic device further comprises: Thin film transistors, where The thin film transistor includes a source electrode and a drain electrode, and The first electrode of the light emitting device is electrically connected to at least one of the source electrode and the drain electrode.
8. The electronic device according to claim 7, further comprising: Color filters, color conversion layers, touch screen layers, polarizing layers, or combinations thereof.
9. Electronic equipment comprising the light emitting device according to any one of claims 1 to 5.
10. The electronic device of claim 8, wherein the electronic device is a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a phone, a portable phone, a tablet computer, a tablet phone, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall with multiple displays stitched together, a theater screen, a stadium screen, a light therapy device, or a sign.
11. A heterocyclic compound represented by Formula 1: [Formula 1] [Formula 2] In formula 1 and formula 2, b1, b6 and b7 are each independently an integer from 0 to 3, b5 is an integer from 0 to 4, Ar1, R1, R 21 to R 24 、R 31 to R 34 and R 41 to R 44 Each is independently a group represented by Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted by at least one R 10a Substituted C6-C 60 Aryloxy groups, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Arylthio group, unsubstituted or substituted with at least one R 10a Substituted C7-C 60 Arylalkyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 heteroarylalkyl group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(═O)(Q1), -S(═O)2(Q1), or -P(═O)(Q1)(Q2), R 31 to R 34 and R 41 to R 44 At least one of them is independently a group represented by Formula 2, Ar2, Ar3 and R5 to R7 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted by at least one R 10a Substituted C6-C 60 Aryloxy groups, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Arylthio group, unsubstituted or substituted with at least one R 10a Substituted C7-C 60 Arylalkyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 heteroarylalkyl group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(═O)(Q1), -S(═O)2(Q1), or -P(═O)(Q1)(Q2), R1, R 21 to R 24 、R 31 to R 34 、R 41 to R 44 and two or more of R5 to R7 are optionally bonded together to form an unsubstituted or substituted group. 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic groups, L1 to L3 are each independently a single bond, unsubstituted or replaced by at least one R 10a Substituted divalent C3-C 60 Carbocyclic groups, either unsubstituted or substituted with at least one R 10a Substituted divalent C1-C 60 Heterocyclic groups, a1 to a3 are each independently an integer from 1 to 5, R 10a yes: deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, or a nitro group; Each unsubstituted or deuterated, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, C2-C 60 Heteroarylalkyl group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 ),-C(=O)(Q 11 )、-S(=O)2(Q 11 ),-P(=O)(Q 11 )(Q 12 ) or a combination thereof substituted C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group or C1-C 60 alkoxy groups; Each unsubstituted or deuterated, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group, C1-C 60 Alkoxy groups, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, C2-C 60 Heteroarylalkyl group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 ),-C(=O)(Q 21 )、-S(=O)2(Q 21 ),-P(=O)(Q 21 )(Q 22 ) or a combination thereof substituted C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group or C2-C 60 a heteroarylalkyl group; or -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 Each independently is: Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group or C1-C 60 an alkoxy group; or Each unsubstituted or deuterated, -F, cyano group, C1-C 60 Alkyl groups, C1-C 60 C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C7-C 60 Arylalkyl group or C2-C 60 heteroarylalkyl groups, and * indicates the binding site with the adjacent atom.
12. The heterocyclic compound according to claim 11, wherein L1 to L3 are each independently: a single key; or Each is unsubstituted or substituted with at least one R 10a Substituted phenyl group, naphthalene group, anthracene group, phenanthrene group, triphenylene group, pyrene group, group, cyclopentadiene group, 1,2,3,4-tetrahydronaphthalene group, thiophene group, furan group, indole group, benzoborole group, benzophosphole group, indene group, benzothiophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzoborole group, dibenzophosphole group, fluorene group, dibenzothiophene group, dibenzogermanol group, dibenzothiophene ... Thiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azaindole group, azabenzoborole group, azabenzophosphole group, azaindene group, azabenzothiorrole group, azabenzogermanium pentadiene group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azadiphenyl a borole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermanol group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, and a quinoline group , a divalent group selected from the group consisting of an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group, and R 10a Same as defined in Formula 1 and Formula 2.
13. The heterocyclic compound according to claim 11, wherein L1 to L3 are each independently: a single key; or A group represented by one of Formula 3-1 to Formula 3-28: In formula 3-1 to formula 3-28, R 10a Same as defined in Equation 1 and Equation 2, c1 is 0 or 1, c2 is an integer from 0 to 2, c3 is an integer from 0 to 3, c4 is an integer from 0 to 4, c6 is an integer from 0 to 6, and * and *' each represent a binding site with an adjacent atom. The heterocyclic compound according to claim 11 , wherein a1 to a3 are each independently an integer of 1 to 3.
15. The heterocyclic compound according to claim 11, wherein Ar1, R1, R 21 to R 24 、R 31 to R 34 and R 41 to R 44 Each independently is: The group represented by Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 20 Alkyl group or C1-C 20 alkoxy groups; Each is deuterated, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, C1-C 10 C1-C12 substituted with an alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group, a pyrimidinyl group, or a combination thereof 20 Alkyl group or C1-C 20 alkoxy groups; Each unsubstituted or deuterated, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, C1-C 10 Alkylphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, yl group, pyrrolyl group, thienyl group, furyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolyl group, isoquinolyl group, benzoquinolyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazole group, a benzothiophene group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophene group, a benzocarbazolyl group, a dibenzothioyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidinyl group, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 ),-P(Q 31 )(Q 32 ),-C(=O)(Q 31 )、-S(=O)2(Q 31 ),-P(=O)(Q 31 )(Q 32 ) or a combination thereof substituted cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, C1-C 10 Alkylphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, yl group, pyrrolyl group, thienyl group, furyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolyl group, isoquinolyl group, benzoquinolyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, a benzothiophenyl group, a benzothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzothiorolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, or an azadibenzothiorolyl group; or -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2), and Q1 to Q3 and Q 31 To Q 33 Each is independently: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; C1-C 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 Alkynyl group; C1-C 60 Alkoxy group; or each unsubstituted or deuterated, -F, cyano group, C1-C 60 Alkyl groups, C1-C 60 C3-C 60 Carbocyclic group or C1-C 60 Heterocyclic group.
16. The heterocyclic compound according to claim 11, wherein Ar2, Ar3 and R5 to R7 are each independently: Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 20 Alkyl group or C1-C 20 alkoxy groups; Each is deuterated, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, C1-C 10 C1-C12 substituted with an alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group, a pyrimidinyl group, or a combination thereof 20 Alkyl group or C1-C 20 alkoxy groups; Each unsubstituted or deuterated, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, C1-C 10 Alkylphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, yl group, pyrrolyl group, thienyl group, furyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolyl group, isoquinolyl group, benzoquinolyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazole group, a benzothiophene group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophene group, a benzocarbazolyl group, a dibenzothioyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidinyl group, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 ),-P(Q 31 )(Q 32 ),-C(=O)(Q 31 )、-S(=O)2(Q 31 ),-P(=O)(Q 31 )(Q 32 ) or a combination thereof substituted cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, C1-C 10 Alkylphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, yl group, pyrrolyl group, thienyl group, furyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolyl group, isoquinolyl group, benzoquinolyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, a benzothiophenyl group, a benzothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzothiorolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, or an azadibenzothiorolyl group; or -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2), and Q1 to Q3 and Q 31 To Q 33 Each is independently: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; C1-C 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 Alkynyl group; C1-C 60 Alkoxy group; or each unsubstituted or deuterated, -F, cyano group, C1-C 60 Alkyl groups, C1-C 60 C3-C 60 Carbocyclic group or C1-C 60 Heterocyclic group.
17. The heterocyclic compound according to claim 11, wherein R 32 to R 34 and R 42 to R 44 At least one of them is each independently a group represented by Formula 2.
18. The heterocyclic compound according to claim 11, wherein R 41 to R 44 At least one of them is each independently a group represented by Formula 2, and R 31 to R 34 are each independently hydrogen or deuterium.
19. The heterocyclic compound according to claim 11, wherein the heterocyclic compound is represented by one of Formula 1-1 to Formula 1-4: In Formulas 1-1 to 1-4, L1, a1, Ar1, R 21 to R 24 、R 31 to R 34 and R 41 to R 44 are each the same as defined in Formula 1, and R 11 to R 14 are each independently the same as defined with respect to R1 in Formula 1.
20. The heterocyclic compound according to claim 11, wherein the heterocyclic compound is one of Compound 1 to Compound 70:
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