Light-emitting device including heterocyclic compound, electronic device including light-emitting device, electronic device including light-emitting device, and heterocyclic compound
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-09-22
- Publication Date
- 2026-03-27
Smart Images

Figure CN121735915A_ABST
Abstract
Description
[0001] Cross-references to related applications
[0002] This application claims priority and benefit to Korean Patent Application No. 10-2024-0130209, filed on September 25, 2024, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field
[0003] The embodiments relate to light-emitting devices including heterocyclic compounds, electronic devices including light-emitting devices, electronic equipment including light-emitting devices, and heterocyclic compounds. Background Technology
[0004] The light-emitting device is a self-emitting device, which has a wide viewing angle, high contrast, short response time, and excellent characteristics in terms of brightness, driving voltage and response speed.
[0005] As an example, the light-emitting device may have a structure in which a first electrode is disposed on a substrate, and a hole transport region, an emitter layer, an electron transport region, and a second electrode are sequentially disposed on the first electrode. Holes supplied from the first electrode move toward the emitter layer through the hole transport region, and electrons supplied from the second electrode move toward the emitter layer through the electron transport region. Charge carriers (e.g., holes and electrons) recombine in the emitter layer to generate excitons. Excitons transition from an excited state to a ground state, thereby generating light.
[0006] It should be understood that this background section is intended to provide useful background for understanding the technology. However, this background section may also include ideas, concepts, or knowledge that were not known or understood by those skilled in the art prior to the effective filing date corresponding to the subject matter disclosed herein. Summary of the Invention
[0007] The embodiments include: a light-emitting device comprising a heterocyclic compound, an electronic device comprising a light-emitting device, an electronic device comprising a light-emitting device, and a heterocyclic compound.
[0008] Other 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 this disclosure.
[0009] According to the implementation method,
[0010] The light-emitting device may include:
[0011] First electrode,
[0012] The second electrode facing the first electrode.
[0013] An interlayer comprising an emission layer between the first and second electrodes, and
[0014] Heterocyclic compounds represented by Formula 1:
[0015] [Formula 1]
[0016]
[0017] In Formula 1,
[0018] Rings CY1 to CY5 can each independently be C5-C 60 carbocyclyl or C2-C 60 heterocyclyl,
[0019] n1 can be an integer selected from 1 to 5,
[0020] L1 can be unsubstituted or substituted with at least one R 10a substituted C3-C 60 carbocyclyl or unsubstituted or substituted with at least one R 10a substituted C1-C 60 heterocyclyl,
[0021] a1 to a5 can each independently be an integer selected from 0 to 10,
[0022] Ar1, Ar2, and R1 to R5 can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazone, unsubstituted or substituted with at least one R 10a substituted C1-C 60 alkyl, unsubstituted or substituted with at least one R 10a substituted C2-C 60 alkenyl, unsubstituted or substituted with at least one R 10a substituted C2-C 60 alkynyl, unsubstituted or substituted with at least one R 10a substituted C1-C 60 alkoxy, unsubstituted or substituted with at least one R 10a substituted C3-C 10 cycloalkyl, unsubstituted or substituted with at least one R 10a substituted C1-C 10 heterocycloalkyl, unsubstituted or substituted with at least one R 10a substituted C3-C 10 cycloalkenyl, unsubstituted or substituted with at least one R 10a substituted C1-C 10 heterocycloalkenyl, unsubstituted or substituted with at least one R 10a substituted C6-C 60 aryl, unsubstituted or substituted with at least one R 10a substituted C6-C 60 aryloxy, unsubstituted or substituted with at least one R 10a substituted C6-C60 arylthio, unsubstituted or substituted with at least one R 10a substituted C7-C 60 aralkyl, unsubstituted or substituted with at least one R 10a substituted C1-C 60 heteroaryl, unsubstituted or substituted with at least one R 10a substituted C1-C 60 heteroaryloxy, unsubstituted or substituted with at least one R 10a substituted C1-C 60 heteroarylthio, unsubstituted or substituted with at least one R 10a substituted monovalent non-aromatic fused polycyclic group, unsubstituted or substituted with at least one R 10a substituted monovalent non-aromatic fused heteropolycyclic group, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2),
[0023] two or more adjacent groups of Ar1, Ar2, and R1to R5may optionally be bonded to one another to form an unsubstituted or substituted C5-C 10a substituted C5-C 60 carbocyclyl, unsubstituted or substituted with at least one R 10a substituted C1-C 60 heterocyclyl,
[0024] R 10a may be:
[0025] deuterium, -F, -CI, -Br, -I, hydroxyl, cyano, or nitro;
[0026] each C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, or C1-C 60 alkoxy: deuterium, -F, -CI, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C3-C 60 carbocyclyl, C1-C 60 heterocyclyl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryloxy, C1-C 60 heteroarylthio, C7-C 60C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 60 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 11 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 12 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 13 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 11 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 12 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 11 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 12 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 11 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 11 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 11 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 12 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8
[0027] C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 60 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 60 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 60 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 60 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 60 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 60 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 60 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 60 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 60 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 60 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 60 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 60 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 60 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 60 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 60 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 60 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 60 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 60 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 60 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 60 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 21 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 22 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 23 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 21 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 22 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 21 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 22 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 21 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 21 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 21 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 22 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8 C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C4-C8
[0028] -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 ) or -P(=O)(Q 31 (Q) 32 ),and
[0029] Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each can be independently:
[0030] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, or nitro; or
[0031] Each of the unsubstituted or replaced groups (deuterium, -F, cyano, C1-C) 60 Alkyl, C1-C 60 C1-C substituted with alkoxy, phenyl, biphenyl or any combination thereof 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C7-C 60 Aryl or C2-C 60 Heteroaryl alkyl groups.
[0032] In an embodiment, the interlayer may further include a hole transport region between the first electrode and the emitter layer, and an electron transport region between the emitter layer and the second electrode; the hole transport region may include a hole injection layer, a hole transport layer, an emitter auxiliary layer, an electron blocking layer, or any combination thereof; and 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.
[0033] In an embodiment, the emitter layer may include a host and a dopant; and the host may include a heterocyclic compound.
[0034] In an embodiment, the light emitting device can 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 can include a heterocyclic compound.
[0035] In an embodiment, the emission layer can emit blue light.
[0036] According to an embodiment, an electronic device can include a light emitting device.
[0037] In an embodiment, the electronic device can further include a thin film transistor electrically connected to the light emitting device; and a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof. In an embodiment, the color conversion layer can include a quantum dot.
[0038] According to an embodiment, an electronic device can include a light emitting device.
[0039] 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 full 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 phablet computer, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro display, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall having a plurality of displays spliced together, a theater screen, a stadium screen, a light therapy device, or a signboard.
[0040] According to an embodiment, the heterocyclic compound can be represented by Formula 1 explained herein.
[0041] In embodiments, each of ring CY1to ring CY5may be independently phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, 1,2-benzo phenanthryl, acenaphthyl, perylenyl, benzopyrenyl, benzo 1,2-benzo phenanthryl, benzotriphenylenyl, fluoranthenyl, chrysenyl, cyclopentadienyl, 1,2,3,4-tetrahydronaphthyl, acridinyl, thiophenyl, furanyl, indolyl, benzoborolyl, benzo phospholyl, indenyl, benzothiazolyl, benzogermyl, benzothiophenyl, benzoselenophenyl, benzofuranyl, benzotellurophenyl, carbazolyl, dibenzoborolyl, dibenzophospholyl, fluorenyl, dibenzothiazolyl, dibenzogermyl, dibenzothiophenyl, dibenzoselenophenyl, dibenzofuranyl, dibenzotellurophenyl, dibenzothiophene-5-oxide, 9H-fluoren-9-one, dibenzothiophene-5,5-dioxide, azaindolyl, azabenzoborolyl, azabenzophospholyl, azaindenyl, azabenzothiazolyl, azabenzogermyl, azabenzothiophenyl, azabenzoselenophenyl, azabenzofuranyl, azacarbazolyl, azadibenzoborolyl, azadibenzophospholyl, azafuorenyl, azadibenzothiazolyl, azadibenzogermyl, azadibenzothiophenyl, azadibenzoselenophenyl, azadibenzofuranyl, azadibenzothiophene-5-oxide, azo-9H-fluoren-9-one, azadibenzothiophene-5,5-dioxide, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, 5,6,7,8-tetrahydroisoquinolinyl, or 5,6,7,8-tetrahydroquinolinyl.
[0042] In embodiments, each of ring CY1to ring CY5may be independently phenyl, naphthyl, or pyridyl.
[0043] In embodiments, L1may be each unsubstituted or substituted with at least one R 10aSubstituted phenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, 1,2-benzophenanthrene, cyclopentadienyl, 1,2,3,4-tetrahydronaphthyl, thiophene, furanyl, indole, benzoboranecyclopentadienyl, benzophoscyclopentadienyl, indene, benzothiophene, benzogermanium cyclopentadienyl, benzothiophene, benzoselenyl, benzofuranyl, carbazole, dibenzoboranecyclopentadienyl, dibenzophoscyclopentadienyl, fluorenyl Dibenzothiophene, dibenzogermanium heterocyclopentadienyl, dibenzothiophene, dibenzoselenyl, dibenzofuranyl, dibenzothiophene-5-oxide, 9H-fluorene-9-one, dibenzothiophene-5,5-dioxide, azaindolyl, azabenzoborone heterocyclopentadienyl, azabenzophosphacyclopentadienyl, azaindenyl, azabenzothiophene, azabenzogermanium heterocyclopentadienyl, azabenzothiophene, azabenzoselenyl Azabenzofuranyl, azacarbazolyl, azadibenzoboronecyclopentadienyl, azadibenzophosphacyclopentadienyl, azafluorenyl, azadibenzothiopheneyl, azadibenzogermanonecyclopentadienyl, azadibenzothiopheneyl, azadibenzofuranyl, azadibenzothiophene-5-oxide, aza-9H-fluoren-9-one, azadibenzothiophene-5,5-dioxide, pyridinyl, pyrimidinyl Pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolineyl, pyrroleyl, pyrazolyl, imidazoleyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiazolyl, benzopyrazolyl, benzimidazolyl, benzooxazolyl, benzothiazolyl, benzooxadiazolyl, benzothiazolyl, 5,6,7,8-tetrahydroisoquinolinyl or 5,6,7,8-tetrahydroquinolinyl; and
[0044] R 10a It can be the same as that specified in Equation 1.
[0045] In an implementation, L1 may be a group represented by one of Formulas 3-1 to 3-30 as explained below.
[0046] In the implementation method, in Equation 1, by The part represented can be the part represented by Equation 6 as explained below.
[0047] In the implementation method, in Equation 1, by The part represented can be one of the parts represented by Equations 6-1 to 6-3 as explained below.
[0048] In the implementation method, R1 to R5 can each be independently:
[0049] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl or C1-C 20Alkoxy;
[0050] Each of the following C1-C is replaced 20 Alkyl or C1-C 20 Alkyl groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, or any combination thereof;
[0051] Each of the following unsubstituted or substituted compounds: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranthyl, triphenylene, pyrene, 1,2-benzophenanthryl, tetraphenylene, pyrrolyl, thiophene, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindoleyl, indoleyl, indazoleyl, purinel, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinolinyl, carbazole, phenanthrylyl, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzyl Benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, dibenzothiophenyl, benzocarbazoleyl, dibenzocarbazoleyl, imidazopyridyl, imidazopyrimidinyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl or azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranthyl, triphenylene, pyrene, 1,2-benzophenanthryl, tetraphenylene, pyrrole, thiophene, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindole, indole, inzolyl, purine, quinolinyl, isoquinolinyl, benzoquinone Phinyl, quinoxalinyl, quinazolinyl, cyclophosphinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzothiazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzothiophene, dibenzocarbazole, imidazopyridyl, imidazopyrimidinyl, -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; or
[0052] -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2), and
[0053] Q1 to Q3 and Q 31 To Q 33 Each can be independently represented as: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkoxy groups; or each of the following unsubstituted or deuterated, -F, cyano, C1-C 60 Alkyl, C1-C 60 C1-C substituted with alkoxy, phenyl, biphenyl or any combination thereof 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C60 carbonyl group, C1-C 60 Heterocyclic group, C7-C 60 Aryl or C2-C 60 Heteroaryl alkyl groups.
[0054] In embodiments, the heterocyclic compound may be represented by one of Formulas 1-1 to 1-4 as explained below.
[0055] In embodiments, the heterocyclic compounds may be compounds 1 to 28 and compounds 30 to 100 as explained below.
[0056] It should be understood that the above embodiments are described in a general and explanatory sense only, and are not intended to be limiting, and this disclosure is not limited to the above embodiments. Attached Figure Description
[0057] The accompanying drawings are included to provide a further understanding of the embodiments, and are incorporated in and constitute a part of this specification. The drawings illustrate embodiments and principles of the present disclosure. The above and other aspects and features of the present disclosure will become more apparent from the detailed description of embodiments of the present disclosure with reference to the accompanying drawings, in which:
[0058] Figure 1 This is a schematic cross-sectional view of the light-emitting device according to an embodiment;
[0059] Figure 2 This is a schematic cross-sectional view of an electronic device according to an embodiment;
[0060] Figure 3 A schematic cross-sectional view of an electronic device according to another embodiment;
[0061] Figure 4 This is a schematic perspective view of an electronic device according to an embodiment;
[0062] Figure 5 This is a schematic perspective view of the exterior of a vehicle, which is an electronic device including a light-emitting device, according to an embodiment; and
[0063] Figures 6A to 6C Each is a schematic diagram of the interior of a vehicle according to an embodiment. Detailed Implementation
[0064] The present disclosure will now be described more fully below with reference to the accompanying drawings, in which embodiments are illustrated. However, the present disclosure may be embodied in various 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.
[0065] In the accompanying drawings, the dimensions (e.g., thickness), scale, and dimensions of the elements may be enlarged for ease of description and clarity. The same reference numerals and / or the same reference characters refer to the same elements throughout.
[0066] In this description, it will be understood that when an element (or area, layer, component, etc.) is described as being "on," "connected to," or "attached to" another element (or area, layer, component, etc.), it may be directly on, directly connected to, or directly attached to the other element (or area, layer, component, etc.), or one or more intervening elements (or areas, layers, components, etc.) may exist between them. In a similar sense, when an element (or area, layer, component, etc.) is described as "covering" another element (or area, layer, component, etc.), it may directly cover the other element (or area, layer, component, etc.), or one or more intervening elements (or areas, layers, components, etc.) may exist between them.
[0067] In the description, when an element is "directly on" another element, "directly connected to" another element, or "directly coupled to" another element, there is no intermediary element. For example, "directly on" can mean that two layers or two elements are disposed without any other element between them (e.g., an adhesive element).
[0068] As used herein, expressions used in the singular, such as “a”, “an”, and “the”, are intended to include the plural form as well, unless the context clearly indicates otherwise.
[0069] As used herein, the term “and / or” includes any and all combinations of one or more related 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 to connect or separate meanings and can be understood as equivalent to “and / or”.
[0070] In the specification and claims, the term "at least one of..." is intended to include the meaning of "at least one selected from the group consisting of..." for the purposes of its meaning and interpretation. For example, "at least one of A, B, and C" can 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 following a list of elements, the term "at least one of..." modifies the entire list of elements and does not modify any individual element in the list.
[0071] It will be understood that although the terms first, second, etc., may be used herein to describe various elements, these elements should not be limited by these terms. These terms are used only to distinguish one element from another. Therefore, without departing from the teachings of this disclosure, a first element may be referred to as a second element. Similarly, without departing from the scope of this disclosure, a second element may be referred to as a first element.
[0072] For ease of description, the spatial relative terms “below,” “under,” “down,” “above,” or “on top,” etc., may be used herein to describe the relationship between one element or component and another, as illustrated in the accompanying drawings. It will be understood that, in addition to the orientations depicted in the drawings, the spatial relative terms are also intended to encompass different orientations of the apparatus in use or operation. For example, in the case of flipping the apparatus illustrated in the drawings, the apparatus located “below” or “under” another apparatus may be placed “on top” of the other apparatus. Accordingly, the interpretative term “below” may include both a lower position and an upper position. The apparatus may also be oriented in other directions, and therefore the spatial relative terms may be interpreted differently depending on the orientation.
[0073] As used herein, the terms “about” or “approximately” include the stated value and mean within an acceptable range of deviation for the stated value, considering that a person skilled in the art would take into account the measurement in question and the errors associated with the measurement of the stated quantity (e.g., limitations of the measurement system). For example, “about” may mean within one or more standard deviations of the stated value, or within ±20%, ±10%, or ±5% of the stated value.
[0074] It should be understood that the terms “comprises,” “comprising,” “includes,” “including,” “have,” “having,” “contains,” and “containing” are intended to indicate the presence of any of the described features, integers, steps, operations, elements, components, or any combination thereof in this disclosure, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or any combination thereof.
[0075] Unless otherwise specified or implied herein, all terms used (including technical and scientific terms) shall have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. It will be further understood that terms, such as those defined in commonly used dictionaries, shall be interpreted as having a meaning consistent with their meaning in the context of the relevant field and shall not be interpreted in an ideal or overly formal sense unless clearly defined in the specification.
[0076] According to an embodiment, the light-emitting device (e.g., an organic light-emitting device) may include: a first electrode; a second electrode facing the first electrode; an interlayer between the first electrode and the second electrode and including an emission layer; and a heterocyclic compound represented by Formula 1.
[0077] The following describes heterocyclic compounds represented by Formula 1.
[0078] [Formula 1]
[0079]
[0080] In Equation 1,
[0081] Rings CY1 to CY5 can each be independently C5-C. 60 Carbocyclic group or C2-C 60 Heterocyclic group,
[0082] n1 can be an integer selected from 1 to 5.
[0083] L1 can be unsubstituted or replaced by at least one R. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,
[0084] a1 to a5 can each be an integer selected from 0 to 10 independently.
[0085] Ar1, Ar2, and R1 through R5 can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 Alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 10 Cycloalkyl, unsubstituted, or with at least one R 10a Replacement C1-C 10 Heterocyclic alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 10 Cycloalkenyl, unsubstituted, or with at least one R 10a Replacement C1-C 10 Heterocyclic alkenyl, unsubstituted, or with at least one R10a Replacement C6-C 60 aryl, unsubstituted, or with at least one R 10a Replacement C6-C 60 aryloxy, unsubstituted, or with at least one R 10a Replacement C6-C 60 Aryl thiols, unsubstituted or with at least one R 10a Replacement C7-C 60 Aryl, unsubstituted or with at least one R 10a Replacement C1-C 60 heteroaryl, unsubstituted or with at least one R 10a Replacement C1-C 60 Heteroaryl groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heteroaryl thiols, unsubstituted or with at least one R 10a Substituted monovalent nonaromatic fused polycyclic groups, unsubstituted or substituted with at least one R 10a Substituted monovalent non-aromatic fused heterocyclic groups, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) or -P(=S)(Q1)(Q2),
[0086] Two or more adjacent groups from Ar1, Ar2, and R1 to R5 may optionally be bonded to each other to form an unsubstituted or substituted compound. 10a Replacement C5-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,
[0087] R 10a Possible forms:
[0088] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro;
[0089] Each of the unsubstituted or substituted C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group or C1-C 60 Alkyl groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C3-C 60 carbonyl group, C1-C 60Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C7-C 60 Aryl alkyl, C2-C 60 heteroaryl, -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;
[0090] Each of the unsubstituted or substituted C3-Cs as described below 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C7-C 60 Aryl or C2-C 60 Heteroalkyl groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C7-C 60 Aryl alkyl, C2-C 60 Heteroaryl, -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; or
[0091] -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 ) or -P(=O)(Q 31 (Q) 32 ),and
[0092] Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each can be independently:
[0093] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, or nitro; or
[0094] Each of the unsubstituted or replaced groups (deuterium, -F, cyano, C1-C) 60 Alkyl, C1-C 60 C1-C substituted with alkoxy, phenyl, biphenyl or any combination thereof 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C7-C 60 Aryl or C2-C 60 Heteroaryl alkyl groups.
[0095] In embodiments, rings CY1 to CY5 can each independently be phenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, 1,2-benzophenanthrene, acenaphthene, perylene, benzopyrene, benzo-1,2-benzophenanthrene, benzotriphenylene, fluoranyl, myristyl, cyclopentadienyl, 1,2,3,4-tetrahydronaphthyl, acridine, thiophene, furanyl, indolyl, benzoboranecyclopentadienyl, benzophoscyclopentadienyl, indene, benzothiophene, benzogermanium heterocyclopentadienyl, benzothiophene alkyl, benzo[selenophenyl], benzo[furanyl], benzo[tellurphenyl], carbazole, dibenzoboranecyclopentadienyl, dibenzophosphacyclopentadienyl, fluorenyl, dibenzothiophenyl, dibenzogermanium heterocyclopentadienyl, dibenzothiophenyl, dibenzo[selenophenyl], dibenzofuranyl, dibenzotellurphenyl, dibenzothiophene-5-oxide, 9H-fluoren-9-one, dibenzothiophene-5,5-dioxide, azaindolyl, azabenzoboranecyclopentadienyl, azabenzophosphacyclopentadienyl, azaindene Azabenzothiophene, azabenzogermanium heterocyclopentadienyl, azabenzothiophene, azabenzoselenene, azabenzofuranyl, azacarbazolyl, azadibenzoborone heterocyclopentadienyl, azadibenzophosphazene, azafluorenyl, azadibenzothiophene, azadibenzogermanium heterocyclopentadienyl, azadibenzothiophene, azadibenzoselenene, azadibenzofuranyl, azadibenzothiophene-5-oxide, aza-9H-fluoren-9-one, azadibenzothiophene Fen-5,5-dioxide, pyridinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolineyl, pyrroleyl, pyrazolyl, imidazoleyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiazolyl, 5,6,7,8-tetrahydroisoquinolinyl or 5,6,7,8-tetrahydroquinolinyl.
[0096] In the embodiments, rings CY1 to CY5 can each be independently phenyl, naphthyl, or pyridyl.
[0097] In the implementation, n1 can be 1 or 2.
[0098] In the implementation, L1 can be either unsubstituted or replaced by at least one R. 10aSubstituted phenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, 1,2-benzophenanthrene, cyclopentadienyl, 1,2,3,4-tetrahydronaphthyl, thiophene, furanyl, indole, benzoboranecyclopentadienyl, benzophoscyclopentadienyl, indene, benzothiophene, benzogermanium cyclopentadienyl, benzothiophene, benzoselenyl, benzofuranyl, carbazole, dibenzoboranecyclopentadienyl, dibenzophoscyclopentadienyl, fluorenyl Dibenzothiophene, dibenzogermanium heterocyclopentadienyl, dibenzothiophene, dibenzoselenyl, dibenzofuranyl, dibenzothiophene-5-oxide, 9H-fluorene-9-one, dibenzothiophene-5,5-dioxide, azaindolyl, azabenzoborone heterocyclopentadienyl, azabenzophosphacyclopentadienyl, azaindenyl, azabenzothiophene, azabenzogermanium heterocyclopentadienyl, azabenzothiophene, azabenzoselenyl alkyl, azidobenzofuranyl, azidocarbazoyl, azidobenzoboranecyclopentadienyl, azidobenzophosphacyclopentadienyl, azidofluorenyl, azidobenzothiophenyl, azidobenzogeranecyclopentadienyl, azidobenzothiophenyl, azidobenzofuranyl, azidobenzothiophene-5-oxide, azido-9H-fluoren-9-one, azidobenzothiophene-5,5-dioxide, pyridyl, pyrimidine 5,6,7,8-tetrahydroisoquinolinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolineyl, pyrroleyl, pyrazolyl, imidazoleyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiazolyl, benzopyrazolyl, benzimidazolyl, benzooxazolyl, benzothiazolyl, benzooxadiazolyl, benzothiazolyl, 5,6,7,8-tetrahydroisoquinolinyl or 5,6,7,8-tetrahydroquinolinyl.
[0099] In an implementation, L1 may be a group represented by one of formulas 3-1 to 3-30:
[0100]
[0101]
[0102] In equations 3-1 to 3-30
[0103] R 10a It can be the same as that described in this article.
[0104] c1 can be 0 or 1.
[0105] c2 can be an integer selected from 0 to 2.
[0106] c3 can be an integer selected from 0 to 3.
[0107] c4 can be an integer selected from 0 to 4.
[0108] c6 can be an integer selected from 0 to 6, and
[0109] * and *' each indicate the bonding site with the adjacent atom.
[0110] In an embodiment, L1 may be a group represented by one of formulas 3-1 to 3-3 and 3-14 to 3-19. In an embodiment, in formula 1, L1 is represented by... The part represented can be the part represented by Equation 6: [Equation 6]
[0111]
[0112] In Equation 6,
[0113] Y2 can be *'-N(Z) 6a )-*”、*'-B(Z 6a )-*”、*'-P(Z 6a )-*”、*'-C(Z 6a (Z) 6b )-*”、*'-Si(Z 6a (Z) 6b )-*”、*'-Ge(Z 6a (Z) 6b )-*”, *'-S-*”, *’-Se-*”, *’-O-*”, *’-C(=O)-*”, *’-S(=O)-*”, *’-S(=O)2-*”, *’-C(=S)-*”, *’-N=*”, *’=N-*”, *'-C(Z 6a )=*”、*'=C(Z 6a )-*”、*'-Si(Z 6a )=*”、*'=Si(Z 6a )-*”、*'-Ge(Z 6a )=*”or*'=Ge(Z 6a )-*”
[0114] b2 can be an integer selected from 0 to 2.
[0115] When b2 is 0, *-(Y2) b2 -*' can be a single key.
[0116] When b2 is 2, the two Y2 values can be the same or different.
[0117] X 61 It can be N or C(Z) 61 ), X 62 It can be N or C(Z) 62 ), X 63 It can be N or C(Z) 63 ), X 64It can be N or C(Z) 64 ), X 65 It can be N or C(Z) 65 ), X 66 It can be N or C(Z) 66 ), X 67 It can be N or C(Z) 67 ), and X 68 It can be N or C(Z) 68 ),
[0118] Z 6a Z 6b and Z 61 To Z 68 Each can be independently compared with reference R. 10a The descriptions are the same.
[0119] Z 6a Z 6b and Z 61 To Z 68 Two or more adjacent groups may optionally be bonded to each other to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, and
[0120] *, *', and *” each indicate the bonding site with the adjacent atom.
[0121] In the implementation method, in Equation 1, by The part represented can be one of the parts represented by equations 6-1 to 6-3:
[0122]
[0123] In equations 6-1 to 6-3,
[0124] X 61 It can be N or C(Z) 61 ), X 62 It can be N or C(Z) 62 ), X 63 It can be N or C(Z) 63 ), X 64 It can be N or C(Z) 64 ), X 65 It can be N or C(Z) 65 ), X 66 It can be N or C(Z) 66 ), X 67 It can be N or C(Z) 67 ), and X 68 It can be N or C(Z)68 ),
[0125] Y 61 It can be O, S, Se, C(Z) 6a (Z) 6b ), Si(Z) 6a (Z) 6b ) or N(Z 6a ),
[0126] Z 6a Z 6b and Z 61 To Z 68 Each can be independently compared with reference R. 10a The descriptions are the same.
[0127] b4 can be an integer selected from 0 to 4.
[0128] b8 can be an integer selected from 0 to 8.
[0129] Z 6a Z 6b and Z 61 To Z 68 Two or more adjacent groups may optionally be bonded to each other to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, and
[0130] * Indicates the bonding site with adjacent atoms.
[0131] In the implementation method, R1 to R5 can each be independently:
[0132] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl or C1-C 20 Alkoxy;
[0133] Each of the following C1-C is replaced 20 Alkyl or C1-C 20 Alkyl groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, or any combination thereof;
[0134] Each of the following unsubstituted or substituted compounds: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranthyl, triphenylene, pyrene, 1,2-benzophenanthryl, tetraphenylene, pyrrolyl, thiophene, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindoleyl, indoleyl, indazoleyl, purinel, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinolinyl, carbazole, phenanthrylyl, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzyl Benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, dibenzothiophenyl, benzocarbazoleyl, dibenzocarbazoleyl, imidazopyridyl, imidazopyrimidinyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl or azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranthyl, triphenylene, pyrene, 1,2-benzophenanthryl, tetraphenylene, pyrrole, thiophene, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindole, indole, inzolyl, purine, quinolinyl, isoquinolinyl, benzoquinone Phinyl, quinoxalinyl, quinazolinyl, cyclophosphinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzothiazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzothiophene, dibenzocarbazole, imidazopyridyl, imidazopyrimidinyl, -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; or
[0135] -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2), and
[0136] Q1 to Q3 and Q 31 To Q 33 Each can be independently represented as: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkoxy groups; or each of the following unsubstituted or deuterated, -F, cyano, C1-C 60 Alkyl, C1-C 60 C1-C substituted with alkoxy, phenyl, biphenyl or any combination thereof 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C7-C 60 Aryl or C2-C 60 Heteroaryl alkyl groups.
[0137] In embodiments, the heterocyclic compound represented by Formula 1 may be represented by one of Formulas 1-1 to 1-4:
[0138] [Equation 1-1]
[0139]
[0140] [Equation 1-2]
[0141]
[0142] [Equation 1-3]
[0143]
[0144] [Equations 1-4]
[0145]
[0146] In equations 1-1 to 1-4, n1, L1, Ar1, and Ar2 can each be the same as those described herein.
[0147] X 11 It can be N or C(R) 11 ), X 12 It can be N or C(R) 12 ), X 13 It can be N or C(R) 13 ), and X 14 It can be N or C(R) 14 ),
[0148] X 21 It can be N or C(R) 21 ), X 22 It can be N or C(R) 22 ), X 23 It can be N or C(R) 23 ), and X 24 It can be N or C(R) 24 ),
[0149] X 31 It can be N or C(R) 31 ), X 32 It can be N or C(R) 32 ), X 33 It can be N or C(R) 33 ), and X 34 It can be N or C(R) 34 ),
[0150] X 41 It can be N or C(R) 41 ), X 42 It can be N or C(R) 42 ), X 43 It can be N or C(R) 43 ), and X 44 It can be N or C(R) 44 ),
[0151] X 51 It can be N or C(R) 51 ), X 52 It can be N or C(R) 52 ), X 53 It can be N or C(R) 53 ), and X 54 It can be N or C(R) 54 ),
[0152] R 11 To R 14 Each can be independently identical to the one described in reference R1.
[0153] R21 To R 24 Each can be independently identical to the one described in reference R2.
[0154] R 31 To R 34 Each can be independently identical to the description in reference R3.
[0155] R 41 To R 44 Each can be independently identical to the one described in reference R4, and
[0156] R 51 To R 54 Each can be independently identical to the one described in reference R5.
[0157] In an embodiment, the heterocyclic compound represented by Formula 1 may include at least one deuterium.
[0158] In an embodiment, the heterocyclic compound represented by Formula 1 may be one of compounds 1 to 28 and compounds 30 to 100:
[0159]
[0160]
[0161]
[0162]
[0163]
[0164]
[0165]
[0166]
[0167]
[0168]
[0169]
[0170] Heterocyclic compounds represented by Formula 1 can suppress intermolecular interactions caused by nonplanar structures with at least 7-membered N-containing heterocycles. Therefore, when heterocyclic compounds represented by Formula 1 are used in the emission layer, color purity and lifetime can be improved.
[0171] In this embodiment, the heterocyclic compound represented by Formula 1 may include at least one N-containing heterocycle, which facilitates control of hole transport characteristics. As a result, the recombination region in the emitter layer is optimized, thereby improving luminescence efficiency when the heterocyclic compound represented by Formula 1 is used in the emitter layer.
[0172] Therefore, light-emitting devices, including those containing heterocyclic compounds represented by Formula 1, can have superior characteristics in terms of driving voltage, luminous efficiency, and lifetime.
[0173] In an embodiment, the heterocyclic compound represented by Formula 1 may have a highest occupied molecular orbital (HOMO) energy level greater than or equal to about -5.8 eV.
[0174] In an embodiment, the heterocyclic compound represented by Formula 1 may have an energy level of a triplet excited state (T1) greater than or equal to about 2.6 eV.
[0175] By referring to the synthetic examples and / or embodiments described herein, those skilled in the art can readily understand the method for synthesizing heterocyclic compounds represented by Formula 1.
[0176] At least one heterocyclic compound represented by Formula 1 can be used in a light-emitting device (e.g., an organic light-emitting device). Therefore, embodiments provide a light-emitting device that may include: a first electrode; a second electrode facing the first electrode; an interlayer between the first and second electrodes and including an emission layer; and a heterocyclic compound represented by Formula 1.
[0177] In the implementation,
[0178] The first electrode of the light-emitting device can be the anode.
[0179] The second electrode of the light-emitting device can be a cathode.
[0180] The interlayer may further include a hole transport region between the first electrode and the emitter layer, and an electron transport region between the emitter layer and the second electrode.
[0181] The hole transport region may include a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer, or any combination thereof, and
[0182] 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.
[0183] The hole transport layer may include a single layer or two or more layers, and the electron transport layer may include a single layer or two or more layers.
[0184] In an embodiment, the heterocyclic compound represented by Formula 1 may be included between the first and second electrodes of the light-emitting device. Therefore, the heterocyclic compound represented by Formula 1 may be included in the interlayer of the light-emitting device, for example, in the emitting layer within the interlayer.
[0185] In an embodiment, the emitting layer in the interlayer of the light-emitting device may include a dopant and a host, wherein the host may include a heterocyclic compound represented by Formula 1. For example, a heterocyclic compound represented by Formula 1 may be used as the host. The emitting layer may emit red, green, blue, and / or white light. In an embodiment, the emitting layer may emit blue light. The blue light may have a maximum emission wavelength in, for example, the range of about 400 nm to about 490 nm. The heterocyclic compound represented by Formula 1 may emit blue light having a maximum emission wavelength in, for example, the range of about 430 nm to about 480 nm.
[0186] In an embodiment, the emitting layer in the interlayer of the light-emitting device may include a dopant and a host, wherein the host may include a heterocyclic compound represented by Formula 1, and the dopant may emit blue light. For example, the dopant may include a transition metal and m ligands, where m may be an integer selected from 1 to 6. The m ligands may be the same or different from each other, at least one of the m ligands may be linked to the transition metal via a carbon-transition metal bond, and the carbon-transition metal bond may be a coordinate bond. For example, at least one of the m ligands may be a carbene ligand (e.g., a carbene ligand in Ir(pmp)3). The transition metal may be, for example, iridium, platinum, osmium, palladium, rhodium, gold, etc. The emitting layer and dopant may be the same as described herein.
[0187]
[0188] In an embodiment, the light-emitting device may further include a capping layer outside the first electrode and / or outside the second electrode.
[0189] 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 and second capping layers may each independently comprise a heterocyclic compound represented by Formula 1. The first and / or second capping layers may be the same as those described herein.
[0190] In an 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.
[0191] In an 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.
[0192] In an embodiment, the light-emitting device may further include a first capping layer outside the first electrode and a second capping layer outside the second electrode. For example, at least one of the first capping layer and the second capping layer may each independently include a heterocyclic compound represented by Formula 1.
[0193] In the specification, the phrase "(interlayer and / or capping layer) includes a heterocyclic compound represented by Formula 1" can be understood as "(interlayer and / or capping layer) may include one heterocyclic compound represented by Formula 1 or two or more different heterocyclic compounds, each independently represented by Formula 1".
[0194] In some embodiments, the interlayer and / or capping layer may comprise only compound 1 as a heterocyclic compound represented by Formula 1. For example, compound 1 may be included in the emitting layer of the light-emitting device. In some embodiments, the interlayer may include both compound 1 and compound 2 as heterocyclic compounds represented by Formula 1. For example, compound 1 and compound 2 may be included in the same layer (e.g., both compound 1 and compound 2 may be included in the emitting layer), or they may be included in different layers (e.g., compound 1 may be included in the emitting layer and compound 2 may be included in the electron transport region).
[0195] In the specification, the term "interlayer" may refer to a single layer and / or multiple layers between the first and second electrodes of the light-emitting device.
[0196] According to an embodiment, the electronic device may include a 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 comprising a source electrode and a drain electrode, wherein a first electrode of the light-emitting device is electrically connected 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 touchscreen layer, a polarizing layer, or any combination thereof. The electronic device may be the same as described herein.
[0197] According to embodiments, electronic devices may include light-emitting devices as described above. Electronic devices may be flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, indoor lights, outdoor lights, signal lights, head-up displays, fully transparent displays, partially transparent displays, flexible displays, rollable displays, foldable displays, stretchable displays, laser printers, telephones, mobile phones, tablet computers, tablet PCs, personal digital assistants (PDAs), wearable devices, laptop computers, digital cameras, camcorders, viewfinders, microdisplays, three-dimensional (3D) displays, virtual reality displays, augmented reality displays, vehicles, video walls with multiple displays spliced together, theater screens, stadium screens, light therapy devices, or signs. Electronic devices may be the same as those described herein.
[0198] [ Figure 1 [Description]
[0199] Figure 1 This is a schematic cross-sectional view of the light-emitting device 10 according to an embodiment. The light-emitting device 10 includes a first electrode 110, a sandwich layer 130, and a second electrode 150.
[0200] The following text is for reference only. Figure 1 The structure of the light-emitting device 10 according to the embodiment and the method of manufacturing the light-emitting device 10 are described.
[0201] [First Electrode 110]
[0202] exist Figure 1 In this embodiment, a substrate may be further included below the first electrode 110 or on the second electrode 150. In this embodiment, the substrate may be a glass substrate or a plastic substrate. In this embodiment, the substrate may be a flexible substrate and may include plastics with excellent heat resistance and durability (e.g., polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof).
[0203] The first electrode 110 can be formed, for example, by depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 can be a high work function material that facilitates hole injection.
[0204] The first electrode 110 may be a reflective electrode, a transmissive-reflective electrode, or a transmissive electrode. 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 embodiments, when the first electrode 110 is a 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.
[0205] The first electrode 110 may have a single-layer structure consisting of a single layer or a multi-layer structure including multiple layers. In an embodiment, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO.
[0206] [Mezzanine 130]
[0207] The interlayer 130 may be disposed on the first electrode 110. The interlayer 130 may include an emitter layer.
[0208] The interlayer 130 may further include a hole transport region between the first electrode 110 and the emitter layer, and an electron transport region between the emitter layer and the second electrode 150.
[0209] In addition to various organic materials, the interlayer 130 may further include metal-containing compounds (e.g., organometallic compounds) or inorganic materials (e.g., quantum dots).
[0210] In an embodiment, the interlayer 130 may include two or more emitting units stacked between the first electrode 110 and the second electrode 150, and at least one charge generating layer between adjacent emitting units in the two or more emitting units. When the interlayer 130 includes two or more emitting units and at least one charge generating layer as described above, the light-emitting device 10 may be a series light-emitting device.
[0211] [Hole transport region in interlayer 130]
[0212] Hole transport regions can have a single-layer structure consisting of a single layer (composed of a single material), a single-layer structure consisting of a single layer comprising different materials, or a multi-layer structure comprising multiple layers containing different materials.
[0213] The hole transport region may include a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer, or any combination thereof.
[0214] In an implementation, the hole transport region may have a multi-layer structure, such as a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission auxiliary layer structure, a hole injection layer / emission auxiliary layer structure, a hole transport layer / emission auxiliary layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure, wherein the layers of each structure may be stacked from the first electrode 110 in the order described therein, but the structure of the hole transport region is not in this way.
[0215] In an implementation, the hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
[0216] [Formula 201]
[0217]
[0218] [Formula 202]
[0219]
[0220] In equations 201 and 202,
[0221] L 201 To L 204 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10aReplacement C1-C 60 Heterocyclic group,
[0222] L 205 It can be *-O-*', *-S-*', or *-N(Q) 201 )-*', unsubstituted or by at least one R 10a Replacement C1-C 20 Alkylene, unsubstituted, or with at least one R 10a Replacement C2-C 20 alkenyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,
[0223] xa1 to xa4 can each be an integer selected from 0 to 5 independently.
[0224] xa5 can be an integer selected from 1 to 10.
[0225] R 201 To R 204 and Q 201 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,
[0226] R 201 and R 202 Optionally via a single bond, unsubstituted, or by at least one R 10a Substituted C1-C5 alkylene groups or unsubstituted or substituted with at least one R 10a The substituted C2-C5 alkenyl groups are linked together to form an unsubstituted or substituted compound with at least one R group. 10a Replacement C8-C 60 Polycyclic groups (e.g., carbazole group) (e.g., compound HT16),
[0227] R 203 and R 204 Optionally via a single bond, unsubstituted, or by at least one R 10a Substituted C1-C5 alkylene groups or unsubstituted or substituted with at least one R 10a The substituted C2-C5 alkenyl groups are linked together to form an unsubstituted or substituted compound with at least one R group. 10a Replacement C8-C 60 Polycyclic groups, and
[0228] na1 can be an integer selected from 1 to 4.
[0229] In embodiments, 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 formulas CY201 to CY217:
[0230]
[0231] In equations CY201 to CY217, R 10b and R 10c Each can be independently compared with reference R. 10a The descriptions are the same, CY ring 201 To CY 204 Each can be independently C3-C 20 Carbocyclic or C1-C 20 Heterocyclic group, and at least one hydrogen in formulas CY201 to CY217 may be unsubstituted or R as described herein. 10a replace.
[0232] In the implementation, in formulas CY201 to CY217, the ring CY 201 To CY 204 Each can be independently phenyl, naphthyl, phenanthryl or anthracene.
[0233] In embodiments, the compounds represented by formula 201 and formula 202 may include at least one of the groups represented by formulas CY201 to CY203.
[0234] In an embodiment, the compound represented by formula 201 may include at least one of the groups represented by formulas CY201 to CY203 and at least one of the groups represented by formulas CY204 to CY217.
[0235] In the implementation, in formula 201, xa1 can be 1, R 201 It can be a group represented by one of the formulas CY201 to CY203, xa2 can be 0, and R 202 It can be a group represented by one of the formulas CY204 to CY207.
[0236] In an embodiment, the compound represented by formula 201 and the compound represented by formula 202 may each not include the groups represented by formulas CY201 to CY203.
[0237] In embodiments, the compound represented by formula 201 and the compound represented by formula 202 may each not include the groups represented by formulas CY201 to CY203 and may each independently include at least one of the groups represented by formulas CY204 to CY217.
[0238] In embodiments, the compounds represented by formula 201 and the compounds represented by formula 202 may each not include the groups represented by formulas CY201 to CY217.
[0239] For example, the hole transport region may include one of compounds HT1 to HT46, m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiroTPD, spiroNPB, 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), CzSi, BCFN, SiCzCz, or any combination thereof:
[0240]
[0241]
[0242]
[0243]
[0244]
[0245] The thickness of the hole transport region can be approximately to approximately Within a certain range. For example, the thickness of the hole transport region can be approximately... to approximately Within the range. 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 can be approximately... to approximately Within this range, and the thickness of the hole transport layer can be approximately to approximately For example, the thickness of the hole injection layer can be approximately to approximately Within a certain range. For example, the thickness of the hole transport layer can be approximately... to approximately Within the above range, when the thickness of the hole transport region, the thickness of the hole injection layer, and the thickness of the hole transport layer are all within the above range, satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage.
[0246] The emission assist layer can increase luminous efficiency by compensating for the optical resonant distance according to the wavelength of the light emitted by the emission layer, and the electron blocking layer can prevent electrons from leaking from the emission layer to the hole transport region. Materials that may be included in the hole transport region may be included in both the emission assist layer and the electron blocking layer.
[0247] [p-dopant]
[0248] In addition to the materials described above, the hole transport region may further include a charge-generating material for improving conductivity. The charge-generating material may be uniformly or non-uniformly dispersed in the hole transport region (e.g., in the form of a single layer composed of the charge-generating material).
[0249] The charge-generating material can be, for example, a p-doped agent.
[0250] For example, the lowest unoccupied molecular orbital (LUMO) energy level of a p-doped agent can be less than or equal to about -3.5 eV.
[0251] In embodiments, p-dopersive agents may include quinone derivatives, cyano-containing compounds, compounds comprising elements EL1 and EL2, or any combination thereof.
[0252] Examples of quinone derivatives may include TCNQ and F4-TCNQ.
[0253] Examples of cyano-containing compounds may include HAT-CN and compounds represented by formula 221:
[0254]
[0255] [Equation 221]
[0256]
[0257] In Equation 221,
[0258] R 221 To R 223 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, and
[0259] R 221 To R 223 At least one of them can be independently replaced by C3-C as described below. 60 Carbocyclic or C1-C 60 Heterocyclic groups: cyano; -F; -Cl; -Br; -I; C1-C substituted with cyano, -F, -Cl, -Br, -I or any combination thereof20 Alkyl groups; or any combination thereof.
[0260] In a compound comprising elements EL1 and EL2, element EL1 may be a metal, a metalloid, or any combination thereof, and element EL2 may be a nonmetal, a metalloid, or any combination thereof.
[0261] 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. (Co, Rhodium (Rh), Iridium (Ir), Nickel (Ni), Palladium (Pd), Platinum (Pt), Copper (Cu), Silver (Ag), Gold (Au), etc.); Post-transition metals (e.g., Zinc (Zn), Indium (In), Tin (Sn), etc.); and Lanthanides (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.).
[0262] Examples of metalloids may include silicon (Si), antimony (Sb), and tellurium (Te).
[0263] Examples of nonmetals may include oxygen (O) and halogens (e.g., F, Cl, Br, I, etc.).
[0264] Examples of compounds including elements EL1 and EL2 may include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides, metal iodides, etc.), quasi-metal halides (e.g., quasi-metal fluorides, quasi-metal chlorides, quasi-metal bromides, quasi-metal iodides, etc.), metal tellurides, or any combination thereof.
[0265] 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.) and rhenium oxides (e.g., ReO3, etc.).
[0266] Examples of metal halides may include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, and lanthanide metal halides.
[0267] 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, and CsI.
[0268] 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, and BaI2.
[0269] 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.), and tantalum halides (e.g., TaF3, TaCl3, Ta...). Br3, 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, ReBr2). Ferrous halides (e.g., FeF2, FeCl2, FeBr2, FeI2), ruthenium halides (e.g., RuF2, RuCl2, RuBr2, RuI2), osmium halides (e.g., OsF2, OsCl2, OsBr2, OsI2), cobalt halides (e.g., CoF2, CoCl2, CoBr2, CoI2), rhodium halides (e.g., RhF2, RhCl2, RhBr2, RhI2), iridium halides (e.g., IrF2, IrCl2, IrB2). (e.g., 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.), cuprous halides (e.g., CuF, CuCl, CuBr, CuI, etc.), silver halides (e.g., AgF, AgCl, AgBr, AgI, etc.) and gold halides (e.g., AuF, AuCl, AuBr, AuI, etc.).
[0270] Examples of post-transition metal halides may include zinc halides (e.g., ZnF2, ZnCl2, ZnBr2, ZnI2, etc.), indium halides (e.g., InI3, etc.) and tin halides (e.g., SnI2, etc.).
[0271] Examples of lanthanide metal halides may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, SmI3, etc.
[0272] Examples of quasi-metal halides may include antimony halides (e.g., SbCl5, etc.).
[0273] 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.), and transition metal tellurides (e.g., TiTe₂, ZrTe₂, HfTe₂, V₂Te₃, Nb₂Te₃, Ta₂Te₃, Cr₂Te₃, Mo₂Te₃, W₂Te₃, MnTe, TcTe, ReTe, F₂Te, etc.). (eTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe, Au2Te, etc.), post-transition metal tellurides (e.g., ZnTe, etc.) and lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.).
[0274] [Emitting layer in interlayer 130]
[0275] When the light-emitting device 10 is a full-color light-emitting device, the emitting layer can be patterned into a red emitting layer, a green emitting layer, and / or a blue emitting layer according to the sub-pixels. In an embodiment, the emitting layer may have a stacked structure having two or more layers selected from red, green, and blue emitting layers, wherein the two or more layers may be in contact with each other or may be separated from each other to emit white light. In an embodiment, the emitting layer may include two or more materials selected from red, green, and blue emitting materials, wherein the two or more materials may be mixed with each other in a single layer to emit white light. In an embodiment, the emitting layer may emit blue light.
[0276] In an implementation, the emission layer may include a heterocyclic compound represented by Formula 1 as described herein.
[0277] The emitter layer may include a host and a dopant.
[0278] In embodiments, the dopant may include heterocyclic compounds represented by Formula 1 as described herein. For example, in addition to heterocyclic compounds represented by Formula 1, the dopant may further include phosphorescent dopant, fluorescent dopant, or any combination thereof. In addition to heterocyclic compounds represented by Formula 1, phosphorescent dopant and fluorescent dopant, etc., may be further included in the emission layer, and may each be the same as described below.
[0279] Based on 100 parts by weight of the host, the amount of dopant in the emitter layer can range from about 0.01 parts by weight to about 15 parts by weight.
[0280] In some implementations, the emission layer may include quantum dots.
[0281] In one embodiment, the emission layer may include a delayed fluorescence material. The delayed fluorescence material may be used as a host material in the emission layer or as a dopant material in the emission layer.
[0282] The thickness of the emission layer can be approximately to approximately Within a certain range. For example, the thickness of the emission layer can be approximately... to approximately Within the aforementioned range, excellent light-emitting properties can be obtained without significantly increasing the driving voltage when the thickness of the emitting layer is within any of the above range.
[0283] [main body]
[0284] In an implementation, the main component may be a heterocyclic compound represented by Formula 1.
[0285] In implementation, the main body may include, for example, a carbazole-containing compound, an anthracene-containing compound, or any combination thereof.
[0286] In an implementation, the main component may include a compound represented by formula 301:
[0287] [Formula 301]
[0288] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 ,
[0289] In Equation 301,
[0290] Ar 301 and L 301 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,
[0291] xb11 can be 1, 2, or 3.
[0292] xb1 can be an integer selected from 0 to 5.
[0293] R 301It can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 Alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -Si(Q) 301 (Q) 302 (Q) 303 -N(Q) 301 (Q) 302 -B(Q) 301 (Q) 302 -C(=O)(Q) 301 -S(=O)2(Q) 301 ) or -P(=O)(Q 301 (Q) 302 ),
[0294] xb21 can be an integer selected from 1 to 5, and
[0295] Q 301 To Q 303 Each can be independently identical to the description in reference Q1.
[0296] In the implementation, in formula 301, when xb11 is 2 or greater, two or more Ar 301 They can be connected to each other via a single key.
[0297] In embodiments, the main body may include a compound represented by formula 301-1, a compound represented by formula 301-2, or any combination thereof:
[0298] [Formula 301-1]
[0299]
[0300] [Formula 301-2]
[0301]
[0302] In Equations 301-1 and 301-2,
[0303] Ring A 301 To Ring A 304 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,
[0304] X 301 It can be O, S, N[(L 304 ) xb4 -R 304 ]、C(R 304 (R) 305 ) or Si(R 304 (R) 305 ),
[0305] xb22 and xb23 can each be 0, 1, or 2 independently.
[0306] L 301 xb1 and R 301 Each can be the same as described in the instruction manual.
[0307] L 302 To L 304 Each can be independently compared with reference L 301 The descriptions are the same.
[0308] xb2 to xb4 can each be independently identical to the description in reference xb1, and
[0309] R 302 To R 305 and R 311 To R 314 Each can be independently compared with reference R. 301 The descriptions are the same.
[0310] In embodiments, the host may include alkaline earth metal complexes, post-transition metal complexes, or any combination thereof. In embodiments, the host may include Be complexes (e.g., compound H55), Mg complexes, Zn complexes, or any combination thereof.
[0311] In embodiments, the main body may include one of compounds H1 to H128, 9,10-bis(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthyl-2-yl)anthracene (MADN), 9,10-bis(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-bis(9-carbazolyl)benzene (mCP), 1,3,5-tris(carbazolyl-9-yl)benzene (TCP), SiTrzCz2, or any combination thereof:
[0312]
[0313]
[0314]
[0315]
[0316]
[0317]
[0318] In an implementation, the main body may include a first main compound and a second main compound.
[0319] In an implementation, the first host compound may be a hole transport host.
[0320] In an implementation, the second host compound may be an electron transport host.
[0321] In implementation, the term "hole transport subject" may refer to a compound that includes a hole transport component.
[0322] In implementation, the term "electron transporter" may refer to a compound that includes an electron transport component or a compound that has bipolar properties.
[0323] In the specification, the terms "hole transport subject" and "electron transport subject" can be understood respectively based on the relative difference between hole mobility and electron mobility in the hole transport subject and the electron transport subject. For example, even if the electron transport subject does not include an electron transport portion, a bipolar compound exhibiting a relatively high electron mobility compared to the hole transport subject can be used as an electron transport subject.
[0324] In the implementation, the hole transport subject can be represented by any one of Equations 311-1 to 311-6, and the electron transport subject can be represented by any one of Equations 312-1 to 312-4 and Equation 313.
[0325] [Equation 311-1]
[0326]
[0327] [Equation 311-2]
[0328]
[0329] [Equation 311-3]
[0330]
[0331] [Equation 311-4]
[0332]
[0333] [Equation 311-5]
[0334]
[0335] [Equation 311-6]
[0336]
[0337] [Equation 312-1]
[0338]
[0339] [Equation 312-2]
[0340]
[0341] [Equation 312-3]
[0342]
[0343] [Equation 312-4]
[0344]
[0345] [Equation 313]
[0346]
[0347] [Formula 313A]
[0348]
[0349] In equations 311-1 to 311-6, 312-1 to 312-4, 313, and 313A
[0350] Ar 301 It can be unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group.10a Replacement C1-C 60 Heterocyclic group,
[0351] A 301 To A 304 Each can be independently C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group,
[0352] X 301 It can be O, S, N[(L 304 ) xb4 -R 304 ]、C[(L 304 ) xb4 -R 304 ][(L 305 ) xb5 -R 305 ] or Si[(L 304 ) xb4 -R 304 ][(L 305 ) xb5 -R 305 ],
[0353] X 302 Y 301 and Y 302 Each can be independently a single bond, O, S, N[(L 305 ) xb5 -R 305 ]、C[(L 304 ) xb4 -R 304 ][(L 305 ) xb5 -R 305 ]、Si[(L 304 ) xb4 -R 304 ][(L 305 ) xb5 -R 305 ] or S(=O)2,
[0354] xb1 to xb5 can each be independently 0, 1, 2, 3, 4 or 5.
[0355] xb6 can be 1, 2, 3, 4, or 5.
[0356] X 321 To X 328 Each can be independently N or C[(L 324 ) xb24 -R 324 ],
[0357] Y 321It can be *-O-*', *-S-*', *-N[(L 325 ) xb25 -R 325 ]-*'、*-C[(L 325 ) xb25 -R 325 ][(L 326 ) xb26 -R 326 ]-*'、*-C[(L 325 ) xb25 -R 325 ]=C[(L 326 ) xb26 -R 326 ]-*'、*-C[(L 325 ) xb25 -R 325 ] = N - *' or * - N = C[(L 326 ) xb26 -R 326 ]-*',
[0358] k21 can be 0, 1, or 2.
[0359] When k21 is 0, Y 321 It may not exist.
[0360] xb21 to xb26 can each be independently 0, 1, 2, 3, 4 or 5.
[0361] A 31 A 32 and A 34 Each can be independently C3-C 60 Carbocyclic or C1-C 30 Heterocyclic group,
[0362] A 33 It can be a group represented by formula 313A.
[0363] X 31 It can be N[(L) 335 ) xb35 -(R 335 )]、O、S、Se、C[(L 335 ) xb35 -(R 335 )][(L 336 ) xb36 -(R 336 )] or Si[(L 335 ) xb35 -(R 335 )][(L 336 ) xb36 -(R 336 )],
[0364] xb31 to xb36 can each be independently 0, 1, 2, 3, 4 or 5.
[0365] xb42 to xb44 can each independently be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.
[0366] L 301 To L 306 L 321 To L 326 and L 331 To L 336 Each can be independently a single bond, unsubstituted, or bonded by at least one R. 10a Replacement C1-C 20 Alkylene, unsubstituted, or with at least one R 10a Replacement C2-C 20 alkenyl, unsubstituted, or with at least one R 10a Replacement C2-C 20 alkyne group, unsubstituted or with at least one R 10a Replacement C3-C 10 Cycloalkylene, unsubstituted, or with at least one R 10a Replacement C1-C 10 Heterocyclic alkyl, unsubstituted or with at least one R 10a Replacement C3-C 10 Cycloalkenyl, unsubstituted or with at least one R 10a Replacement C1-C 10 Heterocyclic alkenyl, unsubstituted or with at least one R 10a Replacement C6-C 60 aryl, unsubstituted or with at least one R 10a Replacement C1-C 60 heteroaryl, unsubstituted or with at least one R 10a Substituted divalent nonaromatic fused polycyclic groups or unsubstituted groups or groups modified by at least one R 10a Substituted divalent non-aromatic fused heterocyclic groups,
[0367] R 301 To R 305 R 311 To R 314 R 321 To R 326 and R 331 To R 336 Each group can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 Alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 10 Cycloalkyl, unsubstituted, or with at least one R 10a Replacement C1-C 10 Heterocyclic alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 10 Cycloalkenyl, unsubstituted, or with at least one R 10a Replacement C1-C 10 Heterocyclic alkenyl, unsubstituted, or with at least one R 10a Replacement C6-C 60 aryl, unsubstituted, or with at least one R 10a Replacement C6-C 60 aryloxy, unsubstituted, or with at least one R 10a Replacement C6-C 60 Aryl thiols, unsubstituted or with at least one R 10a Replacement C1-C 60 heteroaryl, unsubstituted or with at least one R 10a Replacement C1-C 60 Heteroaryl groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heteroaryl thiols, unsubstituted or with at least one R 10a Substituted monovalent nonaromatic fused polycyclic groups, unsubstituted or substituted with at least one R 10a Substituted monovalent non-aromatic fused heterocyclic groups, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) or -P(=S)(Q1)(Q2),
[0368] R 321 To R 326 Two or more adjacent groups may optionally be bonded to each other to form an unsubstituted or R-shaped structure. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C60 Heterocyclic group,
[0369] R 10a Possible forms:
[0370] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro;
[0371] Each of the unsubstituted or substituted C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group or C1-C 60 Alkyl groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C7-C 60 Aryl alkyl, C2-C 60 Heteroaryl, -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;
[0372] Each of the unsubstituted or substituted C3-Cs as described below 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C7-C 60 Aryl or C2-C 60 Heteroalkyl groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60alkynyl group, C1-C 60 Alkoxy, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C7-C 60 Aryl alkyl, C2-C 60 Heteroaryl, -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; or
[0373] -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 ) or -P(=O)(Q 31 (Q) 32 ),and
[0374] Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; or each unsubstituted or replaced by deuterium, -F, cyano, C1-C. 60 Alkyl, C1-C 60 C1-C substituted with alkoxy, phenyl, biphenyl or any combination thereof 60 Alkyl, C2-C 60 alkenyl, C2-C60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group.
[0375] In the embodiments, the first host compound and the second host compound can form an excited-state complex.
[0376] [Phosphorescent dopant]
[0377] Phosphorescent dopants may include at least one transition metal as the center metal.
[0378] Phosphorescent dopants may include monodentate ligands, dipentate ligands, tridentate ligands, tetradentate ligands, pentadentate ligands, hexadentate ligands, or any combination thereof.
[0379] Phosphorescent dopants can be electrically neutral.
[0380] In an embodiment, the phosphorescent dopant may include an organometallic compound represented by formula 401:
[0381] [Formula 401]
[0382] M(L 401 ) xc1 (L 402 ) xc2 ,
[0383] [Formula 402]
[0384]
[0385] In Equations 401 and 402,
[0386] M can be a transition metal (e.g., iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)).
[0387] L 401 The ligand can be represented by Equation 402, and xc1 can be 1, 2, or 3, wherein when xc1 is 2 or greater, two or more L... 401 They can be the same or different from each other.
[0388] L 402 It can be an organic ligand, and xc2 can be 0, 1, 2, 3, or 4, wherein when xc2 is 2 or greater, two or more L... 402 They can be the same or different from each other.
[0389] X 401 and X 402 They can be nitrogen or carbon independently.
[0390] Ring A 401 And Ring A 402 Each can be independently C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group,
[0391] 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 = *',
[0392] X 403 and X 404 Each can be an independent chemical bond (e.g., covalent or coordinate), O, S, N (Q) 413 ), B(Q) 413 ), P(Q 413 ), C(Q 413 (Q) 414 ) or Si(Q 413 (Q) 414 ),
[0393] Q 411 To Q 414 Each can be independently identical to the description in reference Q1.
[0394] R 401 and R 402 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 20 Alkyl, unsubstituted, or with at least one R 10a Replacement C1-C 20 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -Si(Q) 401 (Q) 402 (Q) 403 -N(Q) 401 (Q) 402 -B(Q) 401 (Q) 402 -C(=O)(Q)401 -S(=O)2(Q) 401 ) or -P(=O)(Q 401 (Q) 402 ),
[0395] Q 401 To Q 403 Each can be independently identical to the description in reference Q1.
[0396] xc11 and xc12 can each be an integer selected from 0 to 10 independently, and
[0397] In Equation 402, * and *' each indicate the binding site with M in Equation 401.
[0398] For example, in equation 402, X 401 It can be nitrogen and X 402 It can be carbon, or X 401 and X 402 Each can be nitrogen.
[0399] In the implementation, in formula 401, when xc1 is 2 or greater, two or more L 401 The two rings A 401 Optionally via T as a linking group 402 Connected together, and the two rings A 402 Optionally via T as a linking group 403 Connected together (see compounds PD1 through PD4 and PD7). T 402 and T 403 Each can be independently compared with reference T 401 The descriptions are the same.
[0400] In Equation 401, L 402 It can be an organic ligand. For example, L... 402 It may include halogen groups, diketone groups (e.g., acetylacetone groups), carboxylic acid groups (e.g., pyridine carboxyl groups), -C (=O), isonitrile groups, -CN groups, phosphorus-containing groups (e.g., phosphin groups, phosphite groups, etc.) or any combination thereof.
[0401] In this embodiment, the phosphorescent dopant may include, for example, one of compounds PD1 to PD39, PtON-TBBI, or any combination thereof:
[0402]
[0403]
[0404]
[0405] [Fluorescent dopant]
[0406] Fluorescent dopants may include amine-containing compounds, styrene-containing compounds, or any combination thereof.
[0407] In an embodiment, the fluorescent dopant may include a compound represented by formula 501:
[0408] [Formula 501]
[0409]
[0410] In Equation 501,
[0411] Ar 501 L 501 To L 503 R 501 and R 502 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,
[0412] xd1 to xd3 can each be independently 0, 1, 2, or 3, and
[0413] xd4 can be 1, 2, 3, 4, 5 or 6.
[0414] In the implementation, in formula 501, Ar 501 It can be a fused ring group in which three or more monocyclic groups are fused together (e.g., anthracene, 1,2-benzophenanthrene, pyrene, etc.).
[0415] In the implementation, xd4 can be 2 in Equation 501.
[0416] In this embodiment, the fluorescent dopant may include one of compounds FD1 to FD36, DPVBi, DPAVBi, or any combination thereof:
[0417]
[0418]
[0419]
[0420] [Delayed fluorescence materials]
[0421] In some embodiments, the emitting layer may further include a delayed fluorescence material.
[0422] In the specification, the delayed fluorescence material can be selected from compounds that can emit delayed fluorescence based on the delayed fluorescence emission mechanism.
[0423] Depending on the type of other materials included in the emission layer, the delayed fluorescence material included in the emission layer can be used as a host or as a dopant.
[0424] In this embodiment, the energy difference between the triplet level (eV) and the singlet level (eV) of the delayed fluorescent material can be in the range of about 0 eV to about 0.5 eV. When the energy difference between the triplet level (eV) and the singlet level (eV) of the delayed fluorescent material satisfies the above range, an upconversion from the triplet to the singlet state of the delayed fluorescent material can occur effectively, and therefore, the light-emitting device 10 can have improved luminous efficiency.
[0425] In embodiments, delayed fluorescence materials may include: materials comprising at least one electron donor (e.g., π-electron-rich C3-C). 60 Cyclic groups such as carbazole and at least one electron acceptor (e.g., sulfoxide, cyano, and π-electron-deficient nitrogen-containing C1-C groups). 60 Materials containing cyclic groups, etc.; or including C8-C 60 Polycyclic aromatic compounds, C8-C 60 Polycyclic groups include at least two cyclic groups that are fused together while sharing boron (B).
[0426] In this embodiment, the delayed fluorescence material may include, for example, at least one of compounds DF1 to DF9:
[0427]
[0428] [Quantum dot]
[0429] The emission layer may include quantum dots.
[0430] The specification states that quantum dots can be crystals of semiconductor compounds. Depending on the size of the crystal, quantum dots can emit light of various wavelengths. By adjusting the elemental ratios in the quantum dot compound, quantum dots can emit light of various wavelengths.
[0431] The diameter of quantum dots can be, for example, in the range of about 1 nm to about 10 nm.
[0432] Quantum dots can be synthesized using wet chemical processes, metal-organic chemical vapor deposition (MOCVD), molecular beam epitaxy (MBE), or any similar process.
[0433] Wet chemistry processes involve mixing precursor materials with organic solvents and growing quantum dot crystals. During quantum dot crystal growth, the organic solvent naturally acts as a dispersant coordinating on the surface of the quantum dot crystals and allows for control of the crystal growth. Therefore, wet chemistry processes are easier to perform than vapor deposition methods (such as metal-organic chemical vapor deposition or molecular beam epitaxy) and allow for low-cost control of quantum dot crystal growth.
[0434] Quantum dots may include group III-VI semiconductor compounds, group II-VI semiconductor compounds, group III-V semiconductor compounds, group I-III-VI semiconductor compounds, group IV-VI semiconductor compounds, group IV elements or compounds, or any combination thereof.
[0435] Examples of group II-VI semiconductor compounds may include: binary compounds (e.g., CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, or MgS); ternary compounds (e.g., CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, C... dZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe or MgZnS); quaternary compounds (e.g., CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe or HgZnSTe); and any combination thereof.
[0436] Examples of Group III-V semiconductor compounds may include: binary compounds (e.g., GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, or InSb); ternary compounds (e.g., GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, or InPSb); quaternary compounds (e.g., GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, or InAlPSb); and any combination thereof. In embodiments, the Group III-V semiconductor compounds may further include Group II elements. Examples of group III-V semiconductor compounds that further include group II elements may include InZnP, InGaZnP, and InAlZnP.
[0437] Examples of group III-VI semiconductor compounds may include: binary compounds (e.g., GaS, Ga2S3, GaSe, Ga2Se3, GaTe, InS, InSe, In2Se3, or InTe); ternary compounds (e.g., InGaS3 or InGaSe3); and any combination thereof.
[0438] Examples of group I-III-VI semiconductor compounds may include: ternary compounds (e.g., AgInS, AgInS2, AgInSe2, AgGaS, AgGaS2, AgGaSe2, CuInS, CuInS2, CuInSe2, CuGaS2, CuGaSe2, CuGaO2, AgGaO2, or AgAlO2, etc.); quaternary compounds (e.g., AgInGaS, AgInGaS2, AgInGaSe, AgInGaSe2, CuInGaS, or CuInGaS2, etc.); and any combination thereof.
[0439] Examples of group IV-VI semiconductor compounds may include: binary compounds (e.g., SnS, SnSe, SnTe, PbS, PbSe, or PbTe); ternary compounds (e.g., SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, or SnPbTe); quaternary compounds (e.g., SnPbSSe, SnPbSeTe, or SnPbSTe); and any combination thereof.
[0440] Examples of Group IV elements or compounds may include: single-element materials (such as Si or Ge); binary compounds (such as SiC or SiGe); and any combination thereof.
[0441] Each element included in a compound (such as a binary compound, a ternary compound, or a quaternary compound) may be present in the particles at a uniform concentration or a non-uniform concentration. The formulas for quantum dot compounds as described above may each refer to the type of elements included in the compound, where the elemental ratio of the compound may vary. For example, AgInGaS2 may indicate AgIn x Ga 1-x S2 (where x is a real number satisfying 0 < x < 1).
[0442] In an embodiment, the quantum dots may have a single structure in which the concentration of each element in the quantum dots is uniform, or the quantum dots may have a core-shell structure. In an embodiment, in the case where the quantum dots have a core-shell structure, the material included in the core and the material included in the shell may be different from each other.
[0443] The shell of the quantum dots may be used as a protective layer to prevent chemical denaturation of the core to maintain semiconductor characteristics and / or may be used as a charging layer to impart electrophoretic characteristics to the quantum dots. The shell may be a single layer or multiple layers. The interface between the core and the shell may have a concentration gradient in which the concentration of the material present in the shell decreases toward the center of the core.
[0444] Examples of the shell of the quantum dots may include metal oxides, non-metal oxides, semiconductor compounds, and any combination thereof. Examples of metal oxides or non-metal oxides may include: binary compounds (such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, or NiO); ternary compounds (such as MgAl2O4, CoFe2O4, NiFe2O4, or CoMn2O4); and any combination thereof.
[0445] Examples of semiconductor compounds may include Group III-VI semiconductor compounds, Group II-VI semiconductor compounds, Group III-V semiconductor compounds, Group I-III-VI semiconductor compounds, Group IV-VI semiconductor compounds, and any combination thereof as described herein. For example, semiconductor compounds may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnSTe, GaAs, GaP, GaS, GaSe, AgGaS, AgGaS2, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, and any combination thereof.
[0446] Quantum dots can have a full width at half maximum (FWHM) of an emission wavelength spectrum less than or equal to about 45 nm. For example, quantum dots can have an FWHM of an emission wavelength spectrum less than or equal to about 40 nm. For example, quantum dots can have an FWHM of an emission wavelength spectrum less than or equal to about 30 nm. When the FWHM of a quantum dot is in any of these ranges, the quantum dot can have improved color purity and / or improved color reproducibility. Light emitted through a quantum dot can be emitted in all directions, thus improving the wide viewing angle.
[0447] In the implementation, quantum dots can be spherical, conical, multi-armed, or cubic in shape, or they can be in the form of nanoparticles, nanotubes, nanowires, nanofibers, or nanoplates.
[0448] Because the band gap can be controlled by adjusting the size of the quantum dots or the elemental ratio in the quantum dot compound, light of various wavelengths can be obtained from the quantum dot-containing emission layer. Therefore, by using the aforementioned quantum dots (using quantum dots of different sizes or quantum dots with different elemental ratios in the quantum dot compound), a light-emitting device 10 that emits light of various wavelengths can be implemented. In an embodiment, the size of the quantum dots or the elemental ratio in the quantum dot compound can be selected to emit red, green, and / or blue light. In an embodiment, the quantum dots can be configured to emit white light by combining various colors of light.
[0449] [Electron transport region in interlayer 130]
[0450] The electron transport region may have a single-layer structure consisting of a single layer (composed of a single material), a single-layer structure consisting of a single layer comprising different materials, or a multi-layer structure comprising multiple layers containing different materials.
[0451] 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.
[0452] In an implementation, 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 emitter layer in the order described herein, but the structure of the electron transport region is not limited thereto.
[0453] Electron transport regions (e.g., buffer layers, hole blocking layers, electron control layers, or electron transport layers within electron transport regions) may include metal-free compounds comprising at least one π-electron-deficient nitrogen-containing C1-C group. 60 Cyclic groups.
[0454] In an embodiment, the electron transport region may include a compound represented by Formula 601.
[0455] [Formula 601]
[0456] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21
[0457] In Equation 601,
[0458] Ar 601 and L 601 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,
[0459] xe11 can be 1, 2, or 3.
[0460] xe1 can be 0, 1, 2, 3, 4, or 5.
[0461] R 601 It can be unsubstituted or by at least one R 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -Si(Q) 601 (Q) 602 (Q) 603 -C(=O)(Q) 601 -S(=O)2(Q) 601 ) or -P(=O)(Q 601 (Q) 602 ),
[0462] Q 601 To Q 603 Each can be independently identical to the description in reference Q1.
[0463] xe21 can be 1, 2, 3, 4, or 5, and
[0464] Ar 601 L 601 and R 601 At least one of them can be independently unsubstituted or by at least one R. 10a Substituted π-electron-deficient nitrogen-containing C1-C 60 Cyclic groups.
[0465] In an implementation, in formula 601, when xe11 is 2 or greater, two or more Ar 601 They can be connected together with a single key.
[0466] In the implementation, in formula 601, Ar 601 It can be unsubstituted or by at least one R 10a Substituted anthracene group.
[0467] In an embodiment, the electron transport region may include a compound represented by formula 601-1:
[0468] [Formula 601-1]
[0469]
[0470] In Equation 601-1,
[0471] X 614 It can be N or C(R) 614 ), X 615 It can be N or C(R) 615 ), X 616 It can be N or C(R) 616 ), and X 614 To X 616 At least one of them can be N,
[0472] L 611 To L 613 Each can be independently compared with reference L 601 The descriptions are the same.
[0473] xe611 to xe613 can each be independently identical to the description in reference xe1.
[0474] R 611 To R 613 Each can be independently compared with reference R. 601 The descriptions are the same, and
[0475] R 614 To R 616 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group.
[0476] In the implementation, in formulas 601 and 601-1, xe1 and xe611 to xe613 can each be 0, 1 or 2 independently.
[0477] In embodiments, 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, TSPO1, TPBI, mSiTrz, or any combination thereof:
[0478]
[0479]
[0480]
[0481]
[0482] The thickness of the electron transport region can be approximately to approximately Within a certain range. For example, the thickness of the electron transport region can be approximately... to approximately Within the range. 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 thickness of the hole blocking layer, or the thickness of the electron control layer can each independently be within approximately [a certain range]. to approximately Within a certain range, and the thickness of the electron transport layer can be approximately [missing information]. to approximately For example, the thickness of the buffer layer, the thickness of the hole blocking layer, or the thickness of the electronic control layer can each be independently set to approximately [value missing]. to approximately Within a certain range. For example, the thickness of the electron transport layer can be approximately... to approximately Within these ranges, satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage when the thickness of the buffer layer, hole blocking layer, electronic control layer, electron transport layer, and / or electron transport region are within these ranges.
[0483] In addition to the materials mentioned above, the electron transport region (e.g., the electron transport layer in the electron transport region) may further include a metallic material.
[0484] Metal-containing materials may include alkali metal complexes, alkaline earth metal complexes, or any combination thereof. The metal ion in an alkali metal complex may be Li, Na, K, Rb, or Cs ions, and the metal ion in an alkaline earth metal complex may be Be, Mg, Ca, Sr, or Ba ions. The ligands coordinated to the metal ions of the alkali metal complex or alkaline earth metal complex may independently include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthrene, cyclopentadiene, or any combination thereof.
[0485] In this embodiment, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (Liq) or compound ET-D2:
[0486]
[0487] The electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer may contact (e.g., directly contact) the second electrode 150.
[0488] The electron injection layer can have a single-layer structure consisting of a single layer (composed of a single material), a single-layer structure consisting of a single layer comprising different materials, or a multi-layer structure comprising multiple layers containing different materials.
[0489] The electron injection layer may include alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof.
[0490] Alkali metals may include Li, Na, K, Rb, Cs, or any combination thereof. Alkali earth metals may include Mg, Ca, Sr, Ba, or any combination thereof. Rare earth metals may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
[0491] Alkali metal compounds, alkaline earth metal compounds, and rare earth metal compounds may include oxides, halides (e.g., fluorides, chlorides, bromides, iodides, etc.) or tellurides of alkali metals, alkaline earth metals, and rare earth metals, or any combination thereof.
[0492] Alkali metal compounds may include: alkali metal oxides (e.g., Li₂O, Cs₂O, or K₂O); alkali metal halides (e.g., LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI); or any combination thereof. Alkali earth metal compounds may include alkaline earth metal oxides (e.g., BaO, SrO, CaO, Ba...).x Sr 1-x O (where x is a real number satisfying 0 < x < 1) or Ba x Ca 1-x O (where x is a real number satisfying 0 < x < 1)). The rare earth metal compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof. In an embodiment, the rare earth metal compound may include lanthanide metal telluride. Examples of lanthanide metal telluride may 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, and Lu2Te3.
[0493] The alkali metal complex, alkaline earth metal complex, and rare earth metal complex may include: an alkali metal ion, an alkaline earth metal ion, or a rare earth metal ion; and a ligand bonded to the metal ion (e.g., 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.
[0494] In an embodiment, the electron injection layer may be composed of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof as described above. In an embodiment, the electron injection layer may further include an organic material (e.g., a compound represented by Formula 601).
[0495] In an embodiment, the electron injection layer may be composed of an alkali metal compound (e.g., an alkali metal halide); or the electron injection layer may be composed of an alkali metal 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-deposited layer or a RbI:Yb co-deposited layer, etc.
[0496] When the electron injection layer further includes an organic material, the alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or any combination thereof may be uniformly or non-uniformly dispersed in a matrix including the organic material.
[0497] The thickness of the electron injection layer can be approximately to approximately Within a certain range. For example, the thickness of the electron-injected layer can be approximately... to approximately Within the range described above, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage when the thickness of the electron injection layer is within any of these ranges.
[0498] [Second electrode 150]
[0499] The second electrode 150 may be disposed on the interlayer 130. 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 150 may include a material having a low work function (e.g., a metal, an alloy, a conductive compound, or any combination thereof).
[0500] The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO, or any combination thereof. The second electrode 150 may be a transmission electrode, a transmission-reflection electrode, or a reflection electrode.
[0501] The second electrode 150 may have a single-layer structure or a multi-layer structure.
[0502] [Capping layer]
[0503] The light-emitting device 10 may include a first capping layer outside the first electrode 110 and / or a second capping layer outside the second electrode 150. In embodiments, the light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are stacked in the order described; or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are stacked in the order described; or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are stacked in the order described.
[0504] Light generated in the emitting layer of the interlayer 130 of the light-emitting device 10 can pass through the first electrode 110, which may be a reflective electrode or a transmission electrode, and through the first capping layer to the outside. Light generated in the emitting layer of the interlayer 130 of the light-emitting device 10 can pass through the second electrode 150, which may be a reflective electrode or a transmission electrode, and through the second capping layer to the outside.
[0505] The first and second capping layers can increase the external emission efficiency based on the principle of constructive interference. Correspondingly, the light extraction efficiency of the light-emitting device 10 is increased, thereby increasing the luminous efficiency of the light-emitting device 10.
[0506] The first capping layer and the second capping layer may each comprise a material having a refractive index greater than or equal to about 1.6 (relative to a wavelength of about 589 nm).
[0507] The first capping layer and the second capping layer can each be independently an organic capping layer including organic materials, an inorganic capping layer including inorganic materials, or an organic-inorganic composite capping layer including both organic and inorganic materials.
[0508] At least one of the first and second capping layers may independently comprise a carbocyclic compound, a heterocyclic compound, an amino-containing compound, a porphyrin derivative, a phthalocyanine derivative, a naphthyl phthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, heterocyclic compound, and amino-containing compound may each optionally be substituted with substituents comprising O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In embodiments, at least one of the first and second capping layers may independently comprise an amino-containing compound.
[0509] In an embodiment, at least one of the first capping layer and the second capping layer may each independently comprise a compound represented by formula 201, a compound represented by formula 202, or any combination thereof.
[0510] In an embodiment, at least one of the first capping layer and the second capping layer may each independently comprise one of compounds HT28 to HT33, one of compounds CP1 to CP6, β-NPB, or any combination thereof:
[0511]
[0512]
[0513] [membrane]
[0514] Heterocyclic compounds represented by Formula 1 can be included in various membranes.
[0515] Therefore, according to the embodiments, the film may include a heterocyclic compound represented by Formula 1. The film may be, for example, an optical component (or light control device) (e.g., a color filter, a color conversion component, a capping layer, a light extraction efficiency enhancement layer, a selective light absorption layer, a polarizing layer, or a quantum dot layer, etc.), a light blocking component (e.g., a light reflecting layer or a light absorbing layer, etc.), or a protective component (e.g., an insulating layer or a dielectric layer, etc.).
[0516] [Electronic Devices]
[0517] Light-emitting devices can be included in various electronic devices. For example, electronic devices that include light-emitting devices can be light-emitting devices or authentication devices, etc.
[0518] In addition to the light-emitting device, the electronic device (e.g., the light-emitting device) may further include: a color filter, a color conversion layer, or a color filter and a color conversion layer. The color filter and / or the color conversion layer may be arranged in at least one direction of travel of the light emitted from the light-emitting device. For example, the light emitted from the light-emitting device may be blue light or white light. The light-emitting device may be the same as described above. In embodiments, the color conversion layer may include quantum dots. Quantum dots may be, for example, as described herein.
[0519] An electronic device may include a substrate. The substrate may include a plurality of sub-pixels, a color filter may include a plurality of color filter regions corresponding to the plurality of sub-pixels, and a color conversion layer may include a plurality of color conversion regions corresponding to the plurality of sub-pixels.
[0520] Pixel-defining films can be arranged between multiple subpixels to define each subpixel.
[0521] The color filter may further include a plurality of color filter areas and a light-blocking pattern arranged between the plurality of color filter areas, and the color conversion layer may further include a plurality of color conversion areas and a plurality of light-blocking patterns arranged between the plurality of color conversion areas.
[0522] A color filter region (or color conversion region) may include a first region emitting a first color light, a second region emitting a second color light, and / or a third region emitting a third color light, wherein the first color light, the second color light, and / or the third color light may have different maximum emission wavelengths from each other. In an embodiment, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. In an embodiment, the color filter region (or color conversion region) may include quantum dots. In an embodiment, 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 those described herein. The first, second, and / or third regions may each further include a scatterer.
[0523] In one embodiment, the light-emitting device can emit first light, a first region can absorb the first light to emit first-first-color light, a second region can absorb the first light to emit second-first-color light, and a third region can absorb the first light to emit third-first-color light. In another embodiment, the first-first-color light, the second-first-color light, and the third-first-color light can have different maximum emission wavelengths. For example, the first light can be blue light, the first-first-color light can be red light, the second-first-color light can be green light, and the third-first-color light can be blue light.
[0524] In addition to the light-emitting device as described above, 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 either the source electrode or the drain electrode may be electrically connected to either the first electrode or the second electrode of the light-emitting device.
[0525] Thin-film transistors may further include gate electrodes and gate insulating films, etc.
[0526] The active layer may include crystalline silicon, amorphous silicon, organic semiconductors, and oxide semiconductors, etc.
[0527] The electronic device may further include a sealing portion for sealing the light-emitting device. The sealing portion may be disposed between the color filter and / or color conversion layer and the light-emitting device. The sealing portion allows light from the light-emitting device to be extracted to the outside and prevents ambient air and moisture from penetrating into the light-emitting device. The sealing portion may be a sealing substrate comprising a transparent glass substrate or a plastic substrate. The sealing portion may be a thin-film encapsulation layer comprising at least one layer selected from organic and inorganic layers. When the sealing portion is a thin-film encapsulation layer, the electronic device may be flexible.
[0528] Depending on the intended use of the electronic device, various functional layers may be further included on the sealed portion in addition to color filters and / or color conversion layers. Examples of functional layers may include a touchscreen layer and a polarizing layer. The touchscreen layer may be a pressure-sensitive touchscreen layer, a capacitive touchscreen layer, or an infrared touchscreen layer. The authentication device may be, for example, a biometric authentication device that authenticates an individual using biometric information from a living body (e.g., fingertip, pupil, etc.).
[0529] In addition to the light-emitting device described above, the authentication device may further include a biometric information collector.
[0530] Electronic devices can be applied to a variety of displays, light sources, lighting devices, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, video game consoles, medical tools (e.g., electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram displays, ultrasound diagnostic devices, or endoscope displays), fish finders, various measuring tools, instruments (e.g., instruments for vehicles, aircraft, and ships), and projectors, etc.
[0531] [Electronic Equipment]
[0532] Light-emitting devices can be included in various electronic devices.
[0533] In implementations, electronic devices including light-emitting devices may be flat panel displays, curved displays, computer monitors, medical monitors, televisions, billboards, indoor lights, outdoor lights, signal lights, head-up displays, fully transparent displays, partially transparent displays, flexible displays, rollable displays, foldable displays, stretchable displays, laser printers, telephones, mobile phones, tablet computers, tablet PCs, personal digital assistants (PDAs), wearable devices, laptop computers, digital cameras, camcorders, viewfinders, microdisplays, three-dimensional (3D) displays, virtual reality displays, augmented reality displays, vehicles, video walls with multiple displays spliced together, theater screens, stadium screens, phototherapy devices, or signs.
[0534] Because light-emitting devices excel in luminous efficiency and long lifespan, electronic devices that include light-emitting devices can possess characteristics such as high brightness, high resolution, and low power consumption.
[0535] [ Figure 2 and Figure 3 [Description]
[0536] Figure 2 This is a schematic cross-sectional view of an electronic device according to an embodiment.
[0537] Figure 2 The electronic device includes a substrate 100, a thin-film transistor (TFT), a light-emitting device, and a sealing portion 300 that seals the light-emitting device.
[0538] The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be disposed on the substrate 100. The buffer layer 210 can prevent the penetration of impurities through the substrate 100 and can provide a flat surface on the substrate 100.
[0539] The TFT can 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.
[0540] The active layer 220 may include inorganic semiconductors (e.g., silicon or polysilicon), organic semiconductors or oxide semiconductors, and the active layer 220 may include a source region, a drain region and a channel region.
[0541] 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.
[0542] The interlayer insulating film 250 may be disposed on the gate electrode 240. The interlayer insulating film 250 may be disposed between the gate electrode 240 and the source electrode 260 to insulate the gate electrode 240 from the source electrode 260, and may be disposed between the gate electrode 240 and the drain electrode 270 to insulate the gate electrode 240 from the drain electrode 270.
[0543] The source electrode 260 and the drain electrode 270 may be arranged on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source region and drain region of the active layer 220, and the source electrode 260 and the drain electrode 270 may respectively contact the exposed portions of the source region and drain region of the active layer 220.
[0544] The TFT can be electrically connected to a light-emitting device to drive the light-emitting device, and can be covered and protected by a 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 includes a first electrode 110, a sandwich layer 130, and a second electrode 150.
[0545] 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 connected (e.g., electrically connected) to the exposed portion of the drain electrode 270.
[0546] A pixel defining film 290, including insulating material, may be disposed on the first electrode 110. The pixel defining film 290 may expose an area of the first electrode 110, and an interlayer 130 may be formed in the exposed area of the first electrode 110. The pixel defining film 290 may be a polyimide-based organic film or a polyacrylic acid-based organic film. Although not explicitly stated... Figure 2 As shown, however, at least some layers of the interlayer 130 may extend beyond the upper portion of the pixel-defining film 290 and be provided as a common layer.
[0547] The second electrode 150 may be disposed on the interlayer 130, and the 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.
[0548] The sealing portion 300 may be located on the capping layer 170. The sealing portion 300 may be disposed on the light-emitting device to protect it from moisture and / or oxygen. The sealing portion 300 may include: silicon nitride (SiN) x ), silicon oxide (SiO) xInorganic membranes including indium tin oxide, indium zinc oxide, or any combination thereof; organic membranes including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resins (e.g., polymethyl methacrylate or polyacrylic acid), epoxy resins (e.g., aliphatic glycidyl ether (AGE)), or any combination thereof; or any combination of inorganic and organic membranes.
[0549] Figure 3 This is a schematic cross-sectional view of an electronic device according to another embodiment.
[0550] Figure 3 electronic devices and Figure 2 The difference in the electronic device may lie at least in that the light-shielding pattern 500 and the functional area 400 are further included on the sealing portion 300. The functional area 400 may be a color filter area, a color conversion area, or a combination of a color filter area and a color conversion area. In an embodiment, Figure 3 The light-emitting device included in the electronic device may be a series light-emitting device.
[0551] [ Figure 4 [Description]
[0552] Figure 4 This is a schematic perspective view of an electronic device 1 including a light-emitting device according to an embodiment.
[0553] Electronic device 1, which can be a device for displaying moving or still images, can be not only a portable electronic device (e.g., mobile phone, smartphone, tablet computer, mobile communication terminal, e-notebook computer, e-reader, portable multimedia player (PMP), navigation device, or ultra-mobile personal computer (UMPC)), but also a variety of products (e.g., television, laptop computer, monitor, billboard, or Internet of Things (IoT) device). Electronic device 1 can be any of these products or a part thereof as described above.
[0554] In this embodiment, electronic device 1 may be a wearable device (e.g., a smartwatch, a smart phone, glasses-type display, or head-mounted display (HMD)) or part of a wearable device. However, the embodiment is not limited to this.
[0555] In implementations, examples of electronic device 1 may include a vehicle's dashboard, a center information display (CID) arranged on the vehicle's center console or dashboard, an interior mirror display replacing the vehicle's side mirrors, an entertainment display for the vehicle's rear seats, a display arranged on the back of the front seats, a head-up display (HUD) mounted on the front of the vehicle or projected onto the windshield, or a computer-generated holographic augmented reality head-up display (CGH AR HUD). For ease of explanation,Figure 4 The implementation method of electronic device 1 being a smartphone is explained.
[0556] Electronic device 1 may include a display area DA and a non-display area NDA outside the display area DA. The display device can display images through pixels of a two-dimensional array arranged in the display area DA.
[0557] The non-display area NDA can be an area that does not display an image and may surround (e.g., completely surround) the display area DA. Drivers for providing electrical signals or power to display elements arranged in the display area DA may be arranged in the non-display area NDA. Pads that can be electrically connected to electronic components or printed circuit boards may be arranged in the non-display area NDA.
[0558] In electronic device 1, the length in the x-axis direction and the length in the y-axis direction may be different from each other. In the implementation, such as Figure 4 As shown, the length in the x-axis direction may be less 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 greater than the length in the y-axis direction.
[0559] [ Figure 5 and Figures 6A to 6C [Description]
[0560] Figure 5 This is a schematic perspective view of the exterior of a vehicle 1000, which is an electronic device including a light-emitting device, according to an embodiment. Figures 6A to 6C Each is a schematic diagram of the interior of a vehicle 1000 according to an embodiment.
[0561] refer to Figure 5 , Figure 6A , Figure 6B and Figure 6C Implementations of vehicle 1000 may include various devices for moving objects (e.g., people, objects, or animals) from a point of origin to a destination. Examples of vehicle 1000 in implementations may include vehicles that travel on roads or tracks, boats that move on seas or rivers, and aircraft that fly in the air using the action of air.
[0562] Vehicle 1000 can travel on roads or tracks. Depending on the rotation of at least one wheel, vehicle 1000 can move in a selected or given direction. In embodiments, vehicle 1000 may include three-wheeled or four-wheeled vehicles, construction machinery, two-wheeled vehicles, prime movers, bicycles, and trains traveling on tracks.
[0563] Vehicle 1000 may include a body having an interior and an exterior, and a chassis, which is an external part of the body, on which mechanical equipment necessary for driving is mounted. The body of vehicle 1000 may include a front panel, hood, roof panel, rear panel, trunk, and pillars provided at the boundaries between the doors, etc. The chassis of vehicle 1000 may include a power generation unit, a power transmission unit, a drive unit, a steering unit, a braking unit, a suspension unit, a transmission unit, a fuel unit, front and rear wheels, and left and right wheels, etc.
[0564] Vehicle 1000 may include side window glass 1100, front window glass 1200, side mirror 1300, instrument panel 1400, center console 1500, passenger seat instrument panel 1600 and display device 2.
[0565] The side window 1100 and the front window 1200 can be separated by a pillar arranged between the side window 1100 and the front window 1200.
[0566] Side window 1100 may be mounted on the side of vehicle 1000. In one embodiment, side window 1100 may be mounted on a door of vehicle 1000. Multiple side windows 1100 may be provided and may face each other. In one embodiment, side window 1100 may include a first side window 1110 and a second side window 1120. In one embodiment, the first side window 1110 may be arranged adjacent to instrument panel 1400, and the second side window 1120 may be arranged adjacent to passenger seat dashboard 1600.
[0567] In one embodiment, the side window glass 1100 may be spaced apart from each other in the x-axis direction or in a direction opposite to the x-axis direction. In another 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 in a direction opposite to the x-axis direction. For example, an imaginary straight line L connecting the side window glass 1100 may extend in the x-axis direction or in a direction opposite to the x-axis direction. In another embodiment, an imaginary 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 in a direction opposite to the x-axis direction.
[0568] The front windshield 1200 can be installed at the front of the vehicle 1000. The front windshield 1200 can be arranged between the side windows 1100 facing each other.
[0569] The side mirror 1300 provides a rearward view of the vehicle 1000. The side mirror 1300 can be mounted on the body of the vehicle 1000. In some embodiments, multiple side mirrors 1300 may be provided. For example, one of the multiple side mirrors 1300 may be disposed outside the first side window 1110, and another of the multiple side mirrors 1300 may be disposed outside the second side window 1120.
[0570] The instrument panel 1400 may be positioned in front of the steering wheel. The instrument panel 1400 may include a tachometer, speedometer, coolant temperature gauge, fuel gauge, turn signal indicator, high beam indicator, warning lights, seat belt warning lights, odometer, driving recorder, automatic gear selector indicator, door opening warning light, oil warning light, and / or low fuel warning light.
[0571] The center console 1500 may include a control panel with buttons for adjusting audio devices, air conditioning devices, and seat heaters. The center console 1500 may be located to one side of the instrument panel 1400.
[0572] The passenger seat instrument panel 1600 may be spaced apart from the instrument cluster 1400, and the center console 1500 may be arranged between the instrument cluster 1400 and the passenger seat instrument panel 1600. In one embodiment, the instrument cluster 1400 may be arranged corresponding to a driver's seat (not shown), and the passenger seat instrument panel 1600 may be arranged corresponding to a passenger seat (not shown). In one embodiment, the instrument cluster 1400 may be adjacent to a first side window 1110, and the passenger seat instrument panel 1600 may be adjacent to a second side window 1120.
[0573] In one embodiment, the display device 2 may include a display panel 3, and the display panel 3 may display images. The display device 2 may be arranged inside the vehicle 1000. In another embodiment, the display device 2 may be arranged between side windows 1100 facing each other. The display device 2 may be arranged on at least one of the instrument panel 1400, the center console 1500, and the passenger seat instrument panel 1600.
[0574] Display device 2 may include organic light-emitting display devices, inorganic electroluminescent display devices, and quantum dot display devices, etc. Hereinafter, organic light-emitting display devices including light-emitting devices will be described as examples of display device 2. However, various types of display devices as described above can be used in embodiments.
[0575] refer to Figure 6A The display device 2 can be mounted on the center console 1500. In one embodiment, the display device 2 can display navigation information. In another embodiment, the display device 2 can display information about audio settings, video settings, or vehicle settings.
[0576] refer to Figure 6B The display device 2 can be arranged on the instrument panel 1400. In this embodiment, the instrument panel 1400 can display driving information, etc., via the display device 2. For example, the instrument panel 1400 can digitally display driving information, etc. The instrument panel 1400 can digitally display vehicle information and driving information as images. In this embodiment, the tachometer pointer and gauges, as well as various warning lights or icons, can be displayed via digital signals.
[0577] 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 or arranged on the passenger seat instrument panel 1600. In one embodiment, the display device 2 arranged on the passenger seat instrument panel 1600 may display images related to the information displayed on the instrument panel 1400 and / or the center console 1500. In another embodiment, the display device 2 arranged on the passenger seat instrument panel 1600 may display information different from the information displayed on the instrument panel 1400 and / or the center console 1500.
[0578] [Manufacturing Method]
[0579] The layers constituting the hole transport region, the emission layer, and the electron transport region can be formed in selected regions using various methods (e.g., vacuum deposition, spin coating, casting, Langmuir-Brookett (LB) deposition, inkjet printing, laser printing, and laser-induced thermal imaging).
[0580] When forming layers constituting hole transport regions, emission regions, and electron transport regions by vacuum deposition, the deposition temperature can be in the range of about 100°C to about 500°C, depending on the materials included in the layers to be formed and the structure of the layers to be formed. -8 To about 10 -3 Vacuum levels within the range of Torr and at approximately to approximately Deposition is carried out at deposition rates within a certain range.
[0581] [Terminology limitations]
[0582] As used in this article, the term "C3-C" 60 "Carbocyclic group" can be a cyclic group consisting only of carbon atoms as cyclic atoms and having 3 to 60 carbon atoms, and as used herein, the term "C1-C" is used in conjunction with "C1-C". 60 A "heterocyclic group" can be a cyclic group having 1 to 60 carbon atoms and further including at least one heteroatom as a cyclic atom in addition to carbon atoms. (C3-C) 60 Carbocyclic groups and C1-C 60 The heterocyclic group can be a monocyclic group consisting of a single ring or a polycyclic group in which two or more rings are fused together. In the embodiments, C1-C 60 Heterocyclic groups can have 3 to 61 cyclic atoms.
[0583] As used herein, the term "cyclic group" may include C3-C 60 Carbocyclic or C1-C 60Heterocyclic group.
[0584] As used in this article, the term "π-electron-rich C3-C" 60 A "cyclic group" can be a cyclic group having 3 to 60 carbon atoms and may not include *-N=*' as a cyclic moiety, and as used herein, the term "π-electron-deficient nitrogen-containing C1-C" is used. 60 The "cyclic group" may be a heterocyclic group having 1 to 60 carbon atoms and may include *-N=*' as the cyclic part.
[0585] In the implementation,
[0586] C3-C 60 The carbocyclic group can be a T1 group or a group in which two or more T1 groups are fused together (e.g., cyclopentadienyl, adamantyl, norbornel, phenyl, pentabenyl, naphthyl, azulel, indarabenyl, acenaphthel, phenanthyl, anthracene, fluoranyl, triphenylene, pyrene, 1,2-benzophenantyl, perylene, penfenyl, heptabenyl, tetraphenyl, framyl, hexaphenyl, pentaphenyl, rubiginyl, keratyl, ovoleyl, indyl, fluorenyl, spirodifluorenyl, benzofluorenyl, indophenantyl, or indoanthrayl).
[0587] C1-C 60 The heterocyclic group can be a T2 group, wherein two or more T2 groups are fused together, or wherein at least one T2 group and at least one T1 group are fused together (e.g., pyrrole, thiophene, furanyl, indole, benzoindole, naphthoindole, isoindole, benzoisoindole, naphthoisoindole, benzothiophene, benzofuranyl, carbazole, dibenzothiophene, dibenzofuranyl, dibenzofuranyl, indocarbazole, indolecarbazole, benzofuranyl, benzothiophenecarbazole, benzothiophenecarbazole, benzoindocarbazole, benzocarbazole, benzonaphthofuranyl, benzonaphthophene, benzonaphthothiophene, benzofuranyl, benzofuranyl, dibenzofuranyl, benzofuranyl, dibenzothiophenecarbazole). Fenyl, benzothiophene, dibenzothiophene, pyrazolyl, imidazole, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiazolyl, benzopyrazolyl, benzimidazolyl, benzooxazolyl, benzoisooxazolyl, benzothiazolyl, benzoisothiazolyl, pyridyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinoline Phinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cenolinyl, phthalazinyl, naphthidyl, imidazopyridyl, imidazopyrimidyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazoyl, azafluorenyl, azadibenzothiophenyl, azadibenzofuranyl, etc.
[0588] C3-C rich in π electrons 60 The cyclic group may be a T1 group, a group in which two or more T1 groups are fused together, a T3 group, a group in which two or more T3 groups are fused together, or a group in which at least one T3 group and at least one T1 group are fused together (e.g., C3-C). 60 Carbocyclic, 1H-pyrrole, thiorrole, borocyclopentadienyl, 2H-pyrrole, 3H-pyrrole, thiophene, furanyl, indole, benzoindole, naphthoindole, isoindole, benzoisoindole, naphthoisoindole, benzothiorrole, benzothiophene, benzofuranyl, carbazole, dibenzothiorrole, dibenzothiophene, dibenzofuranyl, indole-carbazole, indole-carbazole, benzofuran-carbazole, benzothiophene-carbazole, benzothiorrole-carbazole, benzoindole-carbazole, benzocarbazole, benzonaphthofuranyl, benzonaphthophene, benzonaphthorrole, benzofuran-dibenzofuranyl, benzofuran-dibenzothiophene or benzothiophene-dibenzothiophene, etc.
[0589] Nitrogen-containing C1-C lacking π electrons 60 The cyclic group may be a T4 group, a group in which two or more T4 groups are fused together, a group in which at least one T4 group and at least one T1 group are fused together, a group in which at least one T4 group and at least one T3 group are fused together, or a group in which at least one T4 group, at least one T1 group and at least one T3 group are fused together (e.g., pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl). Benzisoxazolyl, benzothiazolyl, benzoisothiazolyl, pyridinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinel, cenolinyl, phthalazinyl, naphthinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzothiophene, azadibenzothiophene, and azadibenzofuranyl, etc.
[0590] The T1 group can be cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, cycloheptenyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptane), norbornyl, bicyclo[1.1.1]pentane, bicyclo[2.1.1]hexane, bicyclo[2.2.2]octane, or phenyl.
[0591] The T2 group can be furanyl, thiophene, 1H-pyrrolyl, thiophene, borocyclopentadienyl, 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azathiazolyl, azaboracyclopentadienyl, pyridinyl, pyrimidinyl, pyrazinyl, pyrazinyl, triazinyl, tetraazinyl, pyrrolylalkyl, imidazolylalkyl, dihydropyrrolyl, piperidinyl, tetrahydropyridinyl, dihydropyridinyl, hexahydropyrimidinyl, tetrahydropyrimidinyl, dihydropyrimidinyl, piperazinyl, tetrahydropyrazinyl, dihydropyrazinyl, tetrahydropyrazinyl, or dihydropyrazinyl.
[0592] The T3 group can be furanyl, thiophene, 1H-pyrrole, thiophene, or borocyclopentadienyl, and
[0593] The T4 group can be 2H-pyrrole, 3H-pyrrole, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiazolyl, azirthiolyl, aziboranecyclopentadienyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, or tetraazinyl.
[0594] As used herein, the terms "cyclic group", "C3-C" 60 "Carbocyclic group", "C1-C" 60 Heterocyclic groups, π-electron-rich C3-C 60 "Cyclic groups" or "nitrogen-containing C1-C groups lacking π electrons" 60 "Cyclic group" can be a monovalent or polyvalent group (e.g., divalent, trivalent, or tetravalent group, etc.) fused (e.g., bonded together) with a cyclic group according to the structure of the formula using the corresponding term. For example, "phenyl" can be benzo[a], phenyl, or phenylene, etc., which can be readily understood by those skilled in the art based on the structure of the formula including "phenyl".
[0595] Unit price C3-C 60 Carbocyclic groups and monovalent C1-C 60 Examples of heterocyclic groups may include C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups.
[0596] Divalent C3-C 60 Carbocyclic groups and divalent C1-C 60 Examples of heterocyclic groups may include C3-C 10 Cycloalkylene, C1-C10 Heterocyclic alkyl, C3-C 10 Cycloalkylene, C1-C 10 Heterocyclic alkenyl, C6-C 60 aryl, C1-C 60 Hypoaryl, divalent non-aromatic fused polycyclic groups and divalent non-aromatic fused heterocyclic groups.
[0597] As used in this article, the term "C1-C" 60 "Alkyl" can be a straight-chain or branched monovalent aliphatic hydrocarbon group having 1 to 60 carbon atoms, and examples may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl, and tert-decyl. As used herein, the term "C1-C" refers to... 60 "alkylene" can be C1-C 60 Alkyl groups have the same structure as divalent groups.
[0598] As used in this article, the term "C2-C" 60 "Alkenyl" can be in C2-C 60 The alkyl group has at least one carbon-carbon double bond at its middle or end, and examples may include vinyl, propenyl, and butenyl groups. As used herein, the term "C2-C" refers to... 60 "Alkenyl" can be C2-C 60 Alkenes are divalent groups with the same structure.
[0599] As used in this article, the term "C2-C" 60 "Alkyne group" can be at C2-C 60 The alkyl group has at least one monovalent hydrocarbon group with a carbon-carbon triple bond in the middle or at the end, and examples may include ethynyl and propynyl. As used herein, the term "C2-C" refers to... 60 "Isynyl group" can be related to C2-C 60 Alkynes are divalent groups with the same structure.
[0600] As used in this article, the term "C1-C" 60 "Alkoxy" can be composed of -O(A 101 (where A) 101 Can be C1-C 60 Alkyl groups are monovalent groups, and examples of them may include methoxy, ethoxy, and isopropoxy.
[0601] As used in this article, the term "C3-C"10 "Cycloalkyl" can be a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and examples of it may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, and bicyclo[2.2.2]octyl. As used herein, the term "C3-C" refers to... 10 "Cycloalkylene" can be C3-C 10 Cycloalkyl groups have the same divalent structure.
[0602] As used in this article, the term "C1-C" 10 "Heterocyclic alkyl" can be a monovalent cyclic group having 1 to 10 carbon atoms and further including at least one heteroatom as a cyclic atom in addition to the carbon atoms, and examples may include 1,2,3,4-oxatriazolyl, tetrahydrofuranyl, and tetrahydrothiopheneyl. As used herein, the term "C1-C" refers to... 10 "Heterocyclic alkyl" can be C1-C 10 Heterocyclic alkyl groups have the same divalent structure.
[0603] As used in this article, the term "C3-C" 10 "Cycloalkenyl" can be a monovalent cyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring structure and being non-aromatic, and examples may include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C3-C" refers to... 10 "Iridylene" can be related to C3-C 10 Cycloalkenyl groups are divalent groups with the same structure.
[0604] As used in this article, the term "C1-C" 10 A "heterocyclic alkenyl" group can be a monovalent cyclic group having 1 to 10 carbon atoms in its ring structure, further including at least one heteroatom as a cyclic atom in addition to carbon atoms, and having at least one double bond. C1-C 10 Examples of heterocyclic alkenyl groups may include 4,5-dihydro-1,2,3,4-oxarizolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothiophenyl. As used herein, the term "C1-C" refers to... 10 "Heterocyclic alkenyl" can be C1-C 10 Heterocyclic alkenyl groups are divalent groups with the same structure.
[0605] As used in this article, the term "C6-C" 60 "Aryl" can be a monovalent group in a carbocyclic aromatic system having 6 to 60 carbon atoms, and as used herein, the term "C6-C" refers to... 60"Arylene" can be a divalent group in a carbocyclic aromatic system with 6 to 60 carbon atoms. (C6-C) 60 Examples of aryl groups may include phenyl, pentanenyl, naphthyl, azulel, indole, acenaphthel, phenanthyl, anthrayl, fluoranthyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentanenyl, heptanenyl, tetraphenyl, framyl, hexaphenyl, pentaphenyl, rubiginyl, myristyl, and ovoleyl. When C6-C 60 Aryl and C6-C 60 When each of the aryl groups comprises two or more rings, the individual rings of the two or more rings can fused together.
[0606] As used in this article, the term "C1-C" 60 "Heteroaryl" can be a monovalent group having a heterocyclic aromatic system having 1 to 60 carbon atoms and further including at least one heteroatom as a cyclic atom in addition to carbon atoms. As used herein, the term "C1-C" is used in this context. 60 "Hypo-heteroaryl" can be a divalent group having a heterocyclic aromatic system having 1 to 60 carbon atoms and further including at least one heteroatom as a cyclic atom in addition to carbon atoms. C1-C 60 Examples of heteroaryl groups may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, benzo[a]quinolinyl, isoquinolinyl, benzo[a]isoquinolinyl, quinoxalinyl, benzo[a]quinoxalinyl, quinazolinyl, benzo[a]quinazolinyl, cyclolinyl, phenanthrolinel, phthalazinyl, and naphthidyl. When C1-C 60 heteroaryl and C1-C 60 When each heteroaryl group comprises two or more rings, the individual rings of the two or more rings can fused together.
[0607] As used herein, the term "monovalent nonaromatic fused polycyclic group" can be a monovalent group having two or more rings fused together, with only carbon atoms (e.g., 8 to 60 carbon atoms) as cyclic atoms, and having no aromaticity in its molecular structure when considered as a whole. Examples of monovalent nonaromatic fused polycyclic groups may include indenyl, fluorenyl, spirodifluorenyl, benzo[a]fluorenyl, indeno[a]phenanthryl, and indeno[a]anthrayl. As used herein, the term "divalent nonaromatic fused polycyclic group" can be a divalent group having the same structure as a monovalent nonaromatic fused polycyclic group.
[0608] As used herein, the term “monovalent nonaromatic fused heterocyclic group” can be a monovalent group having two or more rings fused together, further including at least one heteroatom as a cyclic atom in addition to carbon atoms (e.g., 1 to 60 carbon atoms), and having no aromaticity in its molecular structure when considered as a whole. Examples of monovalent non-aromatic fused heterocyclic groups may include pyrrole, thiophene, furanyl, indole, benzoindole, naphthoindole, isoindole, benzoisoindole, naphthoisoindole, benzothiophene, benzofuranyl, carbazole, dibenzothiophene, dibenzofuranyl, azacarbazole, azafluorenyl, azadibenzothiophene, azadibenzothiophene, azadibenzofuranyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, isothiazolyl, oxadiazolyl, thiazolyl Benzopyrazolyl, benzoimidazolyl, benzooxazolyl, benzothiazolyl, benzooxadiazolyl, benzothiadiazolyl, imidazopyridyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, indolecarbazolyl, indolocarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, benzothiophenocarbazolyl, benzoindolocarbazolyl, benzocarbazolyl, benzonaphthiophenyl, benzonaphthiophenyl, benzofuranodibenzofuranyl, benzofuranodibenzothiophenyl, and benzothiophenodibenzothiophenyl. As used herein, the term "divalent nonaromatic fused heteropolycyclic group" can refer to a divalent group having the same structure as a monovalent nonaromatic fused heteropolycyclic group.
[0609] As used in this article, the term "C6-C" 60 "Aryloxy group" can be composed of -O(A 102 (where A) 102 It can be C6-C 60 The aryl group is used to indicate a group, and as used herein, the term "C6-C" is used to refer to a group. 60 "Arylthio" can be formed by -S(A 103 (where A) 103 It can be C6-C 60 (aryl) represents a group.
[0610] As used in this document, the term "C7-C" 60 "Aryl" can be composed of -(A 104 (A) 105 (where A) 104 Can be C1-C 54 Alkylene and A 105 It can be C6-C 59 The aryl group is used to indicate a group, and as used herein, the term "C2-C" is used to refer to a group. 60 "Heteroarylene" can be composed of -(A 106 (A)107 (where A) 106 Can be C1-C 59 Alkylene and A 107 Can be C1-C 59 (Heteroaryl) group. As used herein, the term "C1-C" refers to a group that is not aryl. 60 "Heteroaryloxy" can be composed of -O(A 108 (where A) 108 Can be C1-C 60 (Heteroaryl) groups, and as used herein, the term "C1-C" 60 "Heteroary sulfhydryl" can be composed of -S(A 109 (where A) 109 Can be C1-C 60 (Heteroaryl) represents a group.
[0611] As used in this article, the term "C3-C" 60 "Carbocyclic group" includes C3-C 50 carbonyl group, C3-C 40 carbonyl group, C3-C 30 carbonyl group, C3-C 20 carbonyl group or C3-C 10 carbon cyclo group;
[0612] The term "C1-C" 60 "Heterocyclic groups" include C1-C 50 Heterocyclic groups, C1-C 40 Heterocyclic groups, C1-C 30 Heterocyclic groups, C1-C 20 Heterocyclic groups or C1-C 10 Heterocyclic groups;
[0613] The term "C1-C" 60 "alkyl" includes C1-C 50 Alkyl, C1-C 30 Alkyl, C1-C 20 Alkyl or C1-C 10 alkyl;
[0614] The term "C2-C" 60 "Alkenyl" includes C2-C 30 alkenyl, C2-C 20 alkenyl or C2-C 10 alkenyl;
[0615] The term "C2-C" 60 "Alkyne group" includes C2-C 30 alkynyl group, C2-C 20 Alkyne group or C2-C 10 alkynyl group;
[0616] The term "C1-C" 60 "Alkoxy" includes C1-C 30 Alkoxy, C1-C 20 Alkoxy or C1-C 10 Alkoxy;
[0617] The term "C6-C" 60 "Aryl" includes C6-C 50 Aryl, C6-C 40 Aryl, C6-C 30 Aryl, C6-C 20 Aryl or C6-C 15 Aryl;
[0618] The term "C1-C" 60 "Heteroary aryl" includes C1-C 50 heteroaryl, C1-C 40 heteroaryl, C1-C 30 heteroaryl, C1-C 20 heteroaryl or C1-C 10 Mixed aromatics;
[0619] The term "monovalent non-aromatic fused polycyclic group" includes C8-C 60 Monovalent non-aromatic fused polycyclic groups, C8-C 50 Monovalent non-aromatic fused polycyclic groups, C8-C 40 Monovalent non-aromatic fused polycyclic groups, C8-C 30 Monovalent non-aromatic fused polycyclic groups or C8-C 20 Monovalent non-aromatic fused polycyclic groups;
[0620] The term "monovalent non-aromatic fused heterocyclic group" includes C1-C 60 Monovalent non-aromatic fused heterocyclic groups, C1-C 50 Monovalent non-aromatic fused heterocyclic groups, C1-C 40 Monovalent non-aromatic fused heterocyclic groups, C1-C 30 Monovalent non-aromatic fused heterocyclic groups or C1-C 20 Monovalent non-aromatic fused heterocyclic groups;
[0621] The term "C6-C" 60 "Aryloxy groups" include C6-C 50 Aryloxy group, C6-C 40 Aryloxy group, C6-C 30 Aryloxy group, C6-C 20 aryloxy or C6-C 15 aryloxy;
[0622] The term "C6-C" 60 "Arylthio" includes C6-C50 Arylthio, C6-C 40 Arylthio, C6-C 30 Arylthio, C6-C 20 Aryl thiols or C6-C 15 Arylthio;
[0623] The term "C1-C" 60 "Heteroaryloxyl" includes C1-C 50 Heteroaryloxy, C1-C 40 Heteroaryloxy, C1-C 30 Heteroaryloxy, C1-C 20 Heteroaryloxy or C1-C 15 heteroaryloxy groups;
[0624] The term "C1-C" 60 "Heteroary sulfhydryl" includes C1-C 50 heteroaryl thiols, C1-C 40 heteroaryl thiols, C1-C 30 heteroaryl thiols, C1-C 20 heteroaryl thiols or C1-C 15 heteroaryl thiols;
[0625] The term "C7-C" 60 "Aryl" includes C7-C 50 Aryl group, C7-C 40 Aryl group, C7-C 30 Aryl group, C7-C 20 Aryl or C7-C 15 Aryl alkyl groups; and
[0626] The term "C2-C" 60 "Heteroarylene" includes C2-C 50 Heteroalkyl, C2-C 40 Heteroaryl, C2-C 30 Heteroaryl, C2-C 20 Heteroaryl or C2-C 15 Heteroaryl alkyl groups.
[0627] In the specification, the group "R" 10a "Can be:
[0628] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro;
[0629] Each of the unsubstituted or substituted C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group or C1-C 60Alkyl groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C7-C 60 Aryl alkyl, C2-C 60 Heteroaryl, -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;
[0630] Each of the unsubstituted or substituted C3-Cs as described below 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C7-C 60 Aryl or C2-C 60 Heteroalkyl groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C7-C 60 Aryl alkyl, C2-C 60 Heteroaryl, -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; or
[0631] -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 ) or -P(=O)(Q 31 (Q) 32 ).
[0632] In the instruction manual, Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; or each unsubstituted or replaced by deuterium, -F, cyano, C1-C. 60 Alkyl, C1-C 60 C1-C substituted with alkoxy, phenyl, biphenyl or any combination thereof 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C7-C 60 Aryl or C2-C 60 Heteroaryl alkyl groups.
[0633] As used herein, the term "heteroatom" can refer to any atom other than carbon and hydrogen. Examples of heteroatoms may include O, S, N, P, Si, B, Ge, Se, and any combination thereof.
[0634] The term "transition metals" may include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), and gold (Au).
[0635] In the specification, the terms "Ph" and "PH" each refer to phenyl, the term "Me" refers to methyl, the term "Et" refers to ethyl, and the terms "tert-Bu" and "Bu" refer to ethyl. t Each refers to tert-butyl, and the term "OMe" refers to methyl methacrylate (MMA).
[0636] As used herein, the term "biphenyl" may mean "phenyl substituted with a phenyl group". For example, "biphenyl" may be a phenyl group having a C6-C ratio. 60 Aryl groups are substituted phenyl groups.
[0637] As used herein, the term "terphenyl" may mean "phenyl substituted with biphenyl". For example, "terphenyl" may be a phenyl group having a C6-C substituted molecule. 60 Aryl-substituted C6-C 60 Aryl groups are substituted phenyl groups.
[0638] Unless otherwise specified, as used herein, the symbols *, *' and *” each refer to the bonding site of an adjacent atom in the corresponding formula or part.
[0639] In this specification, the terms "x-axis," "y-axis," and "z-axis" are not limited to the three axes in an orthogonal coordinate system (e.g., a Cartesian coordinate system) and can be interpreted in a broader sense than the three axes in an orthogonal coordinate system. For example, the x-axis, y-axis, and z-axis can describe axes that are orthogonal to each other, or they can describe axes in different directions that are not orthogonal to each other.
[0640] In this specification, "integers selected from 0 to 10" refers to integers selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10. The above description of numerical ranges also applies to any other numerical ranges appearing in this specification, such as integers selected from 0 and 1, integers selected from 0 to 2, integers selected from 0 to 3, integers selected from 0 to 4, integers selected from 0 to 5, integers selected from 0 to 6, integers selected from 0 to 7, integers selected from 0 to 8, and integers selected from 0 to 9, etc.
[0641] The compounds according to the embodiments and the light-emitting devices according to the embodiments will be described in detail below with reference to the following synthesis examples and embodiments. The phrase "using B instead of A" used in describing the synthesis examples means using the same molar equivalent of B instead of A.
[0642] [Synthesis Examples and Embodiments]
[0643] Synthesis Example 1: Synthesis of Compound 1
[0644]
[0645] 1) Synthesis of intermediate [1-A]
[0646] 850 mg (3.0 mmol) of 1-bromo-3-iodobenzene and 730 mg (3.0 mmol) of 9H-tribenzo[b,d,f]aza 290 mg (1.5 mmol) of cuprous iodide, 340 mg (3.0 mmol) of 1,2-diaminocyclohexane, and 1.59 g (7.5 mmol) of tripotassium phosphate were placed in a reaction vessel and suspended in 30 mL of dimethylformamide (DMF). The reaction temperature was raised to 160 °C, and the reaction mixture was stirred under reflux for 12 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and extracted with ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution and dried over sodium sulfate. The residue obtained by solvent removal was separated by column chromatography to obtain 900 mg (2.25 mmol) of the target compound.
[0647] 2) Synthesis of Compound 1
[0648] 900 mg (2.25 mmol) of intermediate [1-A], 750 mg (2.25 mmol) of 9H-3,9'-bicarbazole, 100 mg (0.11 mmol) of tris(dibenzylacetone)dipalladium (Pd2(dba)3), 70 mg (0.18 mmol) of S-Phos, and 430 mg (4.50 mmol) of sodium tert-butoxide (NaOtBu) were placed in a reaction vessel and suspended in 200 mL of toluene. The reaction temperature was raised to 110 °C, and the reaction mixture was stirred under reflux for 12 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and extracted with ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution and dried with sodium sulfate. The residue obtained by solvent removal was separated by column chromatography to obtain 1.08 g (1.67 mmol) of the target compound.
[0649] Synthesis Example 2: Synthesis of Compound 11
[0650]
[0651] Compound 11 was obtained in essentially the same manner as in Synthetic Example 1, except that 1-bromo-3-iodobenzene-2,4,5,6-d4 was used instead of 1-bromo-3-iodobenzene, and 9H-tribenzo[b,d,f]aza- -1,2,3,4,5,6,7,8,10,11,12,13-d12 replaces 9H-tribenzo[b,d,f]aza And 9H-3,9'-bicarbazole-1,1',2,2',3',4,4',5,5',6,6',7,7',8,8'-d15 was used instead of 9H-3,9'-bicarbazole.
[0652] Synthesis Example 3: Synthesis of Compound 31
[0653]
[0654] Compound 31 was obtained in essentially the same manner as in Synthesis Example 1, except that 1-bromo-3-iodo-1,1'-biphenyl was used instead of 1-bromo-3-iodobenzene.
[0655] Synthesis Example 4: Synthesis of Compound 33
[0656]
[0657] Compound 33, 1.01 g (1.33 mmol), was obtained in essentially the same manner as in Synthetic Example 1, except that 1-bromo-3-iodobenzene was replaced with 4'-bromo-3-iodobenzene, and 9H-tribenzo[b,d,f]aza- -1,2,3,4,5,6,7,8,10,11,12,13-d12 replaces 9H-tribenzo[b,d,f]aza And 9H-3,9'-bicarbazole-1,1',2,2',3',4,4',5,5',6,6',7,7',8,8'-d15 was used instead of 9H-3,9'-bicarbazole.
[0658] Synthesis Example 5: Synthesis of Compound 51
[0659]
[0660] Compound 51 was obtained in essentially the same manner as in Synthesis Example 1, except that 3'-phenyl-9H-3,9'-bicarbazole was used instead of 9H-3,9'-bicarbazole.
[0661] Synthesis Example 6: Synthesis of Compound 57
[0662]
[0663] Compound 57 was obtained in essentially the same manner as in Synthesis Example 1, except that 3'-phenyl-9H-2,9'-bicarbazole was used instead of 9H-3,9'-bicarbazole.
[0664] Table 1
[0665]
[0666] [Example 1]
[0667] Corning 15Ω / cm 2 ITO glass substrates were cut to dimensions of 50mm × 50mm × 0.5mm, ultrasonicated with isopropanol and pure water for 5 minutes each, and cleaned by irradiating them with ultraviolet light and exposing them to ozone for 30 minutes. The resulting glass substrates were then mounted on a vacuum deposition apparatus.
[0668] HAT-CN is deposited on a glass substrate to form a structure with... A hole injection layer of a certain thickness is formed, and BCFN as the first hole transport material is vacuum deposited on the hole injection layer. The thickness is such that SiCzCz is vacuum deposited on it as a second hole transport material. The thickness of the hole transport layer is increased to complete its formation.
[0669] Compound 1, SiTrzCz2 as the host, and PtON-TBBI as a phosphorescent dopant were co-deposited on the hole transport layer in a weight ratio of 60:27:13 to form a structure with... The thickness of the emission layer.
[0670] mSiTrz is deposited on the emitter layer to form a structure with... A first electron transport layer of a certain thickness is formed, and mSiTrz and Liq are co-deposited on the first electron transport layer in a 1:1 weight ratio to form a second electron transport layer, thereby completing the process. Formation of an electron transport layer of a certain thickness. LiF, as a metal halide, is deposited on the electron transport layer to form an electron transport layer with... An electron-injected layer of a certain thickness is formed, and Al is vacuum-deposited onto the electron-injected layer to form a layer with [missing information]. The thick LiF / Al electrode is used to complete the fabrication of the organic light-emitting device.
[0671] The materials used in organic light-emitting devices can be represented by the following formula.
[0672]
[0673] [Examples 2 to 6 and Comparative Examples 1 to 6]
[0674] The organic light-emitting device was manufactured in essentially 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.
[0675] Evaluation Example 1
[0676] Using a Keithley MU 236 and a PR650 luminance meter, measurements were taken at 1,000 cd / m² for the organic light-emitting devices according to Examples 1 to 6 and Comparative Examples 1 to 6. 2 The driving voltage (V), color conversion efficiency (luminous efficiency), and lifetime were calculated. The color conversion efficiency ratio and lifetime ratio were calculated relative to the values in Comparative Example 1, where the color conversion efficiency ratio and lifetime ratio of Comparative Example 1 were each set to 100. The results for the driving voltage (V), color conversion efficiency ratio, and lifetime ratio are shown in Table 2.
[0677] Table 2
[0678]
[0679]
[0680]
[0681]
[0682] Referring to the results in Table 2, it can be confirmed that compared with the organic light-emitting devices of Comparative Examples 1 to 6, the organic light-emitting devices of Examples 1 to 6 have lower driving voltage, superior color conversion efficiency, and superior lifespan.
[0683] Light-emitting devices comprising cyclic compounds represented by Formula 1 can have low driving voltage, high luminous efficiency, and long lifespan. In embodiments, high-quality electronic devices and high-quality consumer products can be manufactured by using light-emitting devices.
[0684] Embodiments have been disclosed herein, and although terminology has been used, it is used and interpreted in a general and descriptive sense only and is not intended to be limiting. In some instances, as will be apparent to those skilled in the art, features, characteristics, and / or elements described in connection with embodiments may be used alone or in combination with features, characteristics, and / or elements described in connection with other embodiments, unless otherwise specifically indicated. Accordingly, those skilled in the art will understand that various changes in form and detail may be made without departing from the spirit and scope of this disclosure.
Claims
1. A light-emitting device, comprising: First electrode; The second electrode facing the first electrode; An interlayer comprising an emission layer between the first electrode and the second electrode; as well as Heterocyclic compounds represented by Formula 1: Formula 1 In Equation 1, Rings CY1 to CY5 are each independently C5-C 60 Carbocyclic group or C2-C 60 Heterocyclic group, n1 is an integer selected from 1 to 5. L1 is unsubstituted or replaced by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group, a1 to a5 are each an independent integer selected from 0 to 10. Ar1, Ar2, and R1 through R5 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 Alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 10 Cycloalkyl, unsubstituted, or with at least one R 10a Replacement C1-C 10 Heterocyclic alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 10 Cycloalkenyl, unsubstituted, or with at least one R 10a Replacement C1-C 10 Heterocyclic alkenyl, unsubstituted, or with at least one R 10a Replacement C6-C 60 aryl, unsubstituted, or with at least one R 10a Replacement C6-C 60 aryloxy, unsubstituted, or with at least one R 10a Replacement C6-C 60 Aryl thiols, unsubstituted or with at least one R 10a Replacement C7-C 60 Aryl, unsubstituted or with at least one R 10a Replacement C1-C 60 heteroaryl, unsubstituted or with at least one R 10a Replacement C1-C 60 Heteroaryl groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heteroaryl thiols, unsubstituted or with at least one R 10a Substituted monovalent nonaromatic fused polycyclic groups, unsubstituted or substituted with at least one R 10a Substituted monovalent non-aromatic fused heterocyclic groups, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) or -P(=S)(Q1)(Q2), Ar1, Ar2, and two or more adjacent groups from R1 to R5 are optionally bonded to each other to form an unsubstituted or substituted compound. 10a Replacement C5-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group, R 10a for: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro; Each of the unsubstituted or substituted C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group or C1-C 60 Alkyl groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C7-C 60 Aryl alkyl, C2-C 60 Heteroaryl, -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; Each of the unsubstituted or substituted C3-Cs as described below 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C7-C 60 Aryl or C2-C 60 Heteroalkyl groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C7-C 60 Aryl alkyl, C2-C 60 Heteroaryl, -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; or -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 )或-P(=O)(Q 31 )(Q 32 ), and 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, cyano, or nitro; or Each of the unsubstituted or replaced groups (deuterium, -F, cyano, C1-C) 60 Alkyl, C1-C 60 C1-C substituted with alkoxy, phenyl, biphenyl or any combination thereof 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C7-C 60 Aryl or C2-C 60 Heteroaryl alkyl groups.
2. The light-emitting device according to claim 1, wherein... The interlayer further includes: Hole transport region between the first electrode and the emitter layer; as well as In the electron transport region between the emitter layer and the second electrode, The hole transport region includes a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer, or any combination thereof, and The electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
3. The light-emitting device according to claim 1, wherein... The emission layer includes: main body; and Dopant, and The main body includes the heterocyclic compound.
4. The light-emitting device according to claim 1, further comprising: 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 includes the heterocyclic compound.
5. The light-emitting device according to claim 1, wherein the emitting layer emits blue light.
6. An electronic device comprising a light-emitting device according to any one of claims 1 to 5.
7. The electronic device according to claim 6, further comprising: Thin-film transistors electrically connected to the light-emitting device; as well as Color filters, color conversion layers, touchscreen layers, polarizing layers, or any combination thereof.
8. The electronic device of claim 7, wherein the color conversion layer comprises quantum dots.
9. An electronic device comprising a light-emitting device according to any one of claims 1 to 5.
10. The electronic device according to claim 9, 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 retractable display, a laser printer, a telephone, a mobile phone, a tablet computer, a tablet PC, a personal digital assistant, a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay, a 3D display, a virtual reality display, an augmented reality display, a vehicle, a video wall having multiple displays spliced together, a theater screen, a stadium screen, a phototherapy device, or a sign.
11. A heterocyclic compound represented by Formula 1: Formula 1 In Equation 1, Rings CY1 to CY5 are each independently C5-C 60 Carbocyclic group or C2-C 60 Heterocyclic group, n1 is an integer selected from 1 to 5. L1 is unsubstituted or replaced by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group, a1 to a5 are each an independent integer selected from 0 to 10. Ar1, Ar2, and R1 through R5 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 Alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 10 Cycloalkyl, unsubstituted, or with at least one R 10a Replacement C1-C 10 Heterocyclic alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 10 Cycloalkenyl, unsubstituted, or with at least one R 10a Replacement C1-C 10 Heterocyclic alkenyl, unsubstituted, or with at least one R 10a Replacement C6-C 60 aryl, unsubstituted, or with at least one R 10a Replacement C6-C 60 aryloxy, unsubstituted, or with at least one R 10a Replacement C6-C 60 Aryl thiols, unsubstituted or with at least one R 10a Replacement C7-C 60 Aryl, unsubstituted or with at least one R 10a Replacement C1-C 60 heteroaryl, unsubstituted or with at least one R 10a Replacement C1-C 60 Heteroaryl groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heteroaryl thiols, unsubstituted or with at least one R 10a Substituted monovalent nonaromatic fused polycyclic groups, unsubstituted or substituted with at least one R 10a Substituted monovalent non-aromatic fused heterocyclic groups, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) or -P(=S)(Q1)(Q2), Ar1, Ar2, and two or more adjacent groups from R1 to R5 are optionally bonded to each other to form an unsubstituted or substituted compound. 10a Replacement C5-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group, R 10a for: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro; Each of the unsubstituted or substituted C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group or C1-C 60 Alkyl groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C7-C 60 Aryl alkyl, C2-C 60 Heteroaryl, -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; Each of the unsubstituted or substituted C3-Cs as described below 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C7-C 60 Aryl or C2-C 60 Heteroalkyl groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryloxy, C1-C 60 heteroaryl thiols, C7-C 60 Aryl alkyl, C2-C 60 Heteroaryl, -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; or -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 )或-P(=O)(Q 31 )(Q 32 ), and 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, cyano, or nitro; or Each of the unsubstituted or replaced groups (deuterium, -F, cyano, C1-C) 60 Alkyl, C1-C 60 C1-C substituted with alkoxy, phenyl, biphenyl or any combination thereof 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C7-C 60 Aryl or C2-C 60 Heteroaryl alkyl groups.
12. The heterocyclic compound according to claim 11, wherein rings CY1 to CY5 are each independently phenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyrene, 1,2-benzophenanthrene, acenaphthene, perylene, benzo[pyrene], benzo[1,2-benzo[1,2-benzophenanthrene], benzo[1,2- ... Cyclopentadienyl, benzothiophene, benzoselenophene, benzofuranyl, benzotellurenyl, carbazole, dibenzoborone-cyclopentadienyl, dibenzophosphanecyclopentadienyl, fluorenyl, dibenzothiophene, dibenzogermanone-cyclopentadienyl, dibenzothiophene, dibenzoselenophene, dibenzofuranyl, dibenzotellurenyl, dibenzothiophene-5-oxide, 9H-fluoren-9-one, dibenzothiophene-5,5-dioxide, azaindolyl, azabenzoborone-cyclopentadienyl, azabenzophosphanecyclopentadienyl Dienyl, azaindenyl, azabenzothiophene, azabenzogermanium heterocyclopentadienyl, azabenzothiophene, azabenzoselenyl, azabenzofuranyl, azacarbazoyl, azadibenzoborone heterocyclopentadienyl, azadibenzophosphazenyl, azafluorenyl, azadibenzothiophene, azadibenzogermanium heterocyclopentadienyl, azadibenzothiophene, azadibenzoselenyl, azadibenzofuranyl, azadibenzothiophene-5-oxide, aza-9H-fluoren-9-one, azadi... Benzothiophene-5,5-dioxide, pyridinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinel, pyrroleyl, pyrazolyl, imidazoleyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiazolyl, benzopyrazolyl, benzimidazolyl, benzooxazolyl, benzothiazolyl, benzooxadiazolyl, benzothiazolyl, 5,6,7,8-tetrahydroisoquinolinyl or 5,6,7,8-tetrahydroquinolinyl.
13. The heterocyclic compound according to claim 11, wherein rings CY1 to CY5 are each independently phenyl, naphthyl, or pyridyl.
14. The heterocyclic compound of claim 11, wherein L1 is each unsubstituted or substituted by at least one R 10a Substituted phenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, 1,2-benzophenanthrene, cyclopentadienyl, 1,2,3,4-tetrahydronaphthyl, thiophene, furanyl, indole, benzoboranecyclopentadienyl, benzophoscyclopentadienyl, indene, benzothiophene, benzogermanium cyclopentadienyl, benzothiophene, benzoselenyl, benzofuranyl, carbazole, dibenzoboranecyclopentadienyl, dibenzophoscyclopentadienyl, fluorenyl Dibenzothiophene, dibenzogermanium heterocyclopentadienyl, dibenzothiophene, dibenzoselenyl, dibenzofuranyl, dibenzothiophene-5-oxide, 9H-fluorene-9-one, dibenzothiophene-5,5-dioxide, azaindolyl, azabenzoborone heterocyclopentadienyl, azabenzophosphacyclopentadienyl, azaindenyl, azabenzothiophene, azabenzogermanium heterocyclopentadienyl, azabenzothiophene, azabenzoselenyl Azabenzofuranyl, azacarbazolyl, azadibenzoboronecyclopentadienyl, azadibenzophosphacyclopentadienyl, azafluorenyl, azadibenzothiopheneyl, azadibenzogermanonecyclopentadienyl, azadibenzothiopheneyl, azadibenzofuranyl, azadibenzothiophene-5-oxide, aza-9H-fluoren-9-one, azadibenzothiophene-5,5-dioxide, pyridinyl, pyrimidinyl Pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolineyl, pyrroleyl, pyrazolyl, imidazoleyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiazolyl, 5,6,7,8-tetrahydroisoquinolinyl or 5,6,7,8-tetrahydroquinolinyl, and R 10a Same as that defined in Equation 1.
15. The heterocyclic compound according to claim 11, wherein L1 is a group represented by one of formulas 3-1 to 3-30: In equations 3-1 to 3-30, R 10a Same as that defined in Equation 1, c1 is either 0 or 1. c2 is an integer selected from 0 to 2. c3 is an integer selected from 0 to 3. c4 is an integer selected from 0 to 4. c6 is an integer selected from 0 to 6, and * and *' each indicate the bonding site with the adjacent atom.
16. The heterocyclic compound according to claim 11, wherein in formula 1, by The part represented is the part represented by Equation 6: Formula 6 In Equation 6, Y2 is *'-N(Z 6a )-*", *'-B(Z 6a )-*", *'-P(Z 6a )-*", *'-C(Z 6a )(Z 6b )-*", *'-Si(Z 6a )(Z 6b )-*", *'-Ge(Z 6a )(Z 6b )-*", *'-S-*", *'-Se-*", *'-O-*", *'-C(=O)-*", *'-S(=O)-*", *'-S(=O)2-*", *'-C(=S)-*", *'-N=*", *'=N-*", *'-C(Z 6a )=*", *'=C(Z 6a )-*", *'-Si(Z 6a )=*", *'=Si(Z 6a )-*", *'-Ge(Z 6a )=*" or *'=Ge(Z 6a )-*", b2 is an integer selected from 0 to 2. When b2 is 0, *-(Y2) b2 -*' represents a single key. When b2 is 2, the two Y2 values are either the same or different. X 61 For N or C(Z) 61 ), X 62 For N or C(Z) 62 ), X 63 For N or C(Z) 63 ), X 64 For N or C(Z) 64 ), X 65 For N or C(Z) 65 ), X 66 For N or C(Z) 66 ), X 67 For N or C(Z) 67 ), X 68 For N or C(Z) 68 ), Z 6a Z 6b and Z 61 To Z 68 Each independently represents R in reference equation 1. 10a The same restrictions apply. Z 6a Z 6b and Z 61 To Z 68 Two or more adjacent groups in a compound are optionally bonded to each other to form an unsubstituted compound or a compound with at least one R group. 10a Replacement C5-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, and *, *', and *” each indicate the bonding site with the adjacent atom.
17. The heterocyclic compound according to claim 11, wherein in formula 1, by The part represented is one of the parts represented by equations 6-1 to 6-3: Among them, in equations 6-1 to 6-3, X 61 For N or C(Z) 61 ), X 62 For N or C(Z) 62 ), X 63 For N or C(Z) 63 ), X 64 For N or C(Z) 64 ), X 65 For N or C(Z) 65 ), X 66 For N or C(Z) 66 ), X 67 For N or C(Z) 67 ), X 68 For N or C(Z) 68 ), Y 61 For O, S, Se, C(Z) 6a (Z) 6b ), Si(Z) 6a (Z) 6b ) or N(Z 6a Z 6a Z 6b and Z 61 To Z 68 Each independently of R in reference equation 1 10a With the same constraints, b4 is an integer selected from 0 to 4. b8 is an integer selected from 0 to 8. Z 6a Z 6b and Z 61 To Z 68 Two or more adjacent groups in a compound are optionally bonded to each other to form an unsubstituted compound or a compound with at least one R group. 10a Replacement C5-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, and * Indicates the bonding site with adjacent atoms.
18. The heterocyclic compound according to claim 11, wherein R1 to R5 are each independently: Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl or C1-C 20 Alkoxy; Each of the following C1-C is replaced 20 Alkyl or C1-C 20 Alkyl groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, or any combination thereof; Each of the following unsubstituted or substituted compounds: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranthyl, triphenylene, pyrene, 1,2-benzophenanthryl, tetraphenylene, pyrrolyl, thiophene, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindoleyl, indoleyl, indazoleyl, purinel, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinolinyl, carbazole, phenanthrylyl, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzyl Benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, dibenzothiophenyl, benzocarbazoleyl, dibenzocarbazoleyl, imidazopyridyl, imidazopyrimidinyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiophenyl, azafluorenyl or azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, C1-C 10 Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranthyl, triphenylene, pyrene, 1,2-benzophenanthryl, tetraphenylene, pyrrole, thiophene, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindole, indole, inzolyl, purine, quinolinyl, isoquinolinyl, benzoquinone Phinyl, quinoxalinyl, quinazolinyl, cyclophosphinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzothiazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophene, benzocarbazole, dibenzothiophene, dibenzocarbazole, imidazopyridyl, imidazopyrimidinyl, -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; or -C(Q1)(Q2)(Q3), -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 of the following is independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; or each of the following unsubstituted or substituted groups: deuterium, -F, cyano, C1-C. 60 Alkyl, C1-C 60 C1-C substituted with alkoxy, phenyl, biphenyl or any combination thereof 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 60 carbonyl group, C1-C 60 Heterocyclic group, C7-C 60 Aryl or C2-C 60 Heteroaryl alkyl groups.
19. The heterocyclic compound according to claim 11, wherein the heterocyclic compound is represented by one of formulas 1-1 to 1-4: Formula 1-1 Formula 1-2 Formula 1-3 Formula 1-4 In equations 1-1 to 1-4, n1, L1, Ar1, and Ar2 are each the same as those defined in equation 1, and X 11 For N or C(R) 11 ), X 12 For N or C(R) 12 ), X 13 For N or C(R) 13 ), X 14 For N or C(R) 14 ), X 21 For N or C(R) 21 ), X 22 For N or C(R) 22 ), X 23 For N or C(R) 23 ), X 24 For N or C(R) 24 ), X 31 For N or C(R) 31 ), X 32 For N or C(R) 32 ), X 33 For N or C(R) 33 ), X 34 For N or C(R) 34 ), X 41 For N or C(R) 41 ), X 42 For N or C(R) 42 ), X 43 For N or C(R) 43 ), X 44 For N or C(R) 44 ), X 51 For N or C(R) 51 ), X 52 For N or C(R) 52 ), X 53 For N or C(R) 53 ), X 54 For N or C(R) 54 ), R 11 To R 14 Each is independently identical to R1 defined in Reference Equation 1. R 21 To R 24 Each is independently identical to R2 in reference equation 1. R 31 To R 34 Each is independently identical to R3 in reference equation 1. R 41 To R 44 Each is independently identical to R4 in Reference Equation 1, and R 51 To R 54 Each is independently identical to R5 in Reference Equation 1.
20. The heterocyclic compound of claim 11, wherein the heterocyclic compound is one of compounds 1 to 28 and compounds 30 to 100:
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