Organic compound, photoelectric element including the same, and electronic device and electronic apparatus including the same
By using organic compounds of specific chemical formulas as the photoactive layer material, the evaporation stability and heat resistance of photoelectric elements are solved, the external quantum efficiency is improved, and the dark current density is reduced, and efficient photoelectric conversion is achieved.
Patent Information
- Application Number
- CN202510123799.1
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2024-02-01
- Filing Date
- 2025-01-26
- Publication Date
- 2025-08-01
AI Technical Summary
The existing photoelectric components have shortcomings in evaporation stability and heat resistance, and the external quantum efficiency and dark current density need to be improved.
Organic compounds represented by specific chemical formulas are used as the photoactive layer materials, including electron-donating groups and electron-receiving groups, absorb green or red light through the conjugated groups, improve evaporation stability and heat resistance, and optimize external quantum efficiency and dark current density.
The high evaporation stability and heat resistance of the photoelectric components are achieved, the external quantum efficiency is improved, the dark current density is reduced, and the photoelectric conversion efficiency is improved.
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Figure CN120398823A_ABST
Abstract
Description
Technical Field
[0001] Disclosed are an organic compound, an optoelectronic device including the same, and an electronic device and an electronic equipment including the optoelectronic device. Background Art
[0002] An optoelectronic device is a device that converts light energy or an optical signal into electrical energy or an electrical signal. Examples of optoelectronic devices include a photovoltaic cell or a solar cell that converts light energy into electrical energy, and a photodetector or a photosensor that detects light energy and converts it into an electrical signal.
[0003] The optoelectronic device may include an organic compound that can be excited by light. The optoelectronic device may have a structure in which a first electrode is disposed over a substrate, and an intermediate layer and a second electrode are sequentially formed over the first electrode. In addition, the intermediate layer of the optoelectronic device is referred to as a photoactive layer, and may include an electron supply layer containing an electron donor and an electron acceptor layer containing an electron acceptor. As the electron donor, a p-type semiconductor material (e.g., SubPC) may be used, and as the electron acceptor, an n-type semiconductor material (e.g., Fullerene) may be used.
[0004] When light irradiates the optoelectronic device, absorption of the light causes excitation of electrons and generation of holes, and the excited electrons and the newly generated holes may form a pair to form an exciton. The exciton moves to the interface of the intermediate layer, and is again separated into an electron and a hole according to the characteristics of the interface. The separated electron and hole move to the respective electrodes, thereby generating a current.
[0005] An electronic device including an optoelectronic device and a light-emitting device is being developed. Light emitted from the light-emitting device may be reflected from an object (e.g., a user's finger) in contact with the electronic device and incident on the optoelectronic device. The optoelectronic device may recognize contact between the object and the electronic device by detecting incident light energy and converting it into an electrical signal. The optoelectronic device may be used as a fingerprint recognition sensor or the like. Summary of the Invention
[0006] Provided are an organic compound having excellent evaporation stability and heat resistance, an optoelectronic device having excellent external quantum efficiency, a high-quality electronic device using the same, and an electronic equipment.
[0007] According to one aspect, provided is an organic compound represented by the following Chemical Formula 1:
[0008] <Chemical Formula 1>
[0009]
[0010] In Chemical Formula 1,
[0011] Ar3 is C1-C60 a heteroarylene or divalent non-aromatic heterocondensed polycyclic group,
[0012] n3 is an integer from 1 to 3,
[0013] L1 is an unsubstituted or R1-substituted C3-C 60 carbocyclic group or an unsubstituted or R1-substituted C1-C 60 heterocyclic group,
[0014] L2 is an unsubstituted or R2-substituted C3-C 60 carbocyclic group or an unsubstituted or R2-substituted C1-C 60 heterocyclic group,
[0015] n1 and n2 are each independently an integer from 1 to 3,
[0016] CY1 and CY2 are each independently a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group,
[0017] X 11 and X 12 are each independently C(R 41 )(R 42 ), Si(R 41 )(R 42 ), N(R 41 ), P(R 41 ), O, S, C(R 41 ), Si(R 41 ), N, P, C(=O), C(=S) or C=C(R 43 )(R 44 ),
[0018] X 11 and X 12 at least one of which is C(=O), C(=S) or C=C(R 43 )(R 44 ),
[0019] X 21 and X 22 are each independently C(R 51 )(R 52 ), Si(R 51 )(R 52 ), N(R 51 ), P(R 51 ), O, S, C(R 51 ), Si(R 51), N, P, C(=O), C(=S) or C=C(R 53 )(R 54 ),
[0020] X 21 and X 22 at least one of which is C(=O), C(=S) or C=C(R 53 )(R 54 ),
[0021] a3, a4 and a5 are each independently an integer from 0 to 10,
[0022] R1 to R5, R 41 , R 42 , R 51 and R 52 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 10a alkyl which is unsubstituted or substituted by at least one R 60 , C2-C 10a alkenyl which is unsubstituted or substituted by at least one R 60 , C2-C 10a alkynyl which is unsubstituted or substituted by at least one R 60 , C1-C 10a alkoxy which is unsubstituted or substituted by at least one R 60 , C3-C 10a carbocyclic group which is unsubstituted or substituted by at least one R 60 , C1-C 10a heterocyclic group which is unsubstituted or substituted by at least one R 60 , C6-C 10a aryloxy which is unsubstituted or substituted by at least one R 60 , C6-C 10a arylthio which is unsubstituted or substituted by at least one R 10a , C7-C 60 aralkyl which is unsubstituted or substituted by at least one R 10a , C2-C 60 heteroaralkyl, -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),
[0023] R 43 , R 44 , R 53 and R 54 and R54 Each is independently an electron-withdrawing group,
[0024] R 10a is
[0025] deuterium (-D), -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
[0026] unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl, C2-C 60 heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 ), -N(Q 11 )(Q 12 ), -B(Q 11 )(Q 12 ), -C(=O)(Q 11 ), -S(=O)2(Q 11 ), -P(=O)(Q 11 )(Q 12 ) or any combination thereof-substituted C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 alkoxy;
[0027] unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl, C2-C 60 heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 ), -N(Q 21 )(Q 22 ), -B(Q 21 )(Q 22), -C(=O)(Q 21 ), -S(=O)2(Q 21 ), -P(=O)(Q 21 )(Q 22 ), or a C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl or C2-C 60 heteroaralkyl; or
[0028] -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), or -P(=O)(Q 31 )(Q 32 ),
[0029] Q1 to Q3, Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 are each independently
[0030] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, or
[0031] unsubstituted or substituted by deuterium, -F, cyano, C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl, or any combination thereof, of C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C7-C 60 aralkyl or C2-C 60 heteroaralkyl.
[0032] According to another aspect, there is provided an optoelectronic device including: a first electrode; a second electrode facing the first electrode; and a photoactive layer disposed between the first electrode and the second electrode and including one or more of the organic compounds.
[0033] According to another aspect, there is provided an electronic device including: the optoelectronic device; a light-emitting element that does not overlap with the optoelectronic device; and a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof.
[0034] According to another aspect, there is provided an electronic device including the optoelectronic device, and the electronic device is a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, indoor or outdoor lighting and / or a signal lamp, a head-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a 3D display, a virtual reality or augmented reality display, a vehicle, a video wall including multiple displays tiled together, a theater or stadium screen, a light therapy device, a plaque, an automotive sensor, a home sensor, and a solar cell.
[0035] The organic compound represented by Chemical Formula 1 can effectively absorb green light or red light by including an electron-donating group, an electron-withdrawing group, and a conjugation group of an appropriate length between the electron-donating group and the electron-withdrawing group. In addition, the organic compound represented by Chemical Formula 1 can have excellent evaporation stability and heat resistance by including vinyl deuterium. Accordingly, the optoelectronic device employing the organic compound can have excellent external quantum efficiency and dark current density. BRIEF DESCRIPTION OF THE DRAWINGS
[0036] Figure 1 FIG. schematically shows an optoelectronic device according to an example of the present invention.
[0037] Figure 2 FIG. schematically shows a light-emitting element included in an electronic device according to an example of the present invention.
[0038] Figure 3 FIG. schematically shows an optoelectronic device according to another example of the present invention.
[0039] Figure 4 FIG. schematically shows an optoelectronic device according to still another example of the present invention.
[0040] Figure 5 FIG. is a diagram schematically showing an electronic device according to an example of the present invention.
[0041] Figure 6 FIG. is a diagram schematically showing an electronic device according to another example of the present invention.
[0042] Figure 7 FIG. is a perspective view schematically showing an electronic device including a photoelectric element according to an example of the present invention.
[0043] Figure 8 FIG. is a diagram schematically showing the exterior of a vehicle as an electronic device including a photoelectric element according to an example of the present invention.
[0044] Figures 9a to 9c FIG. schematically shows Figure 8 the interior of the vehicle.
[0045] (Description of reference numerals)
[0046] 10: Light-emitting element 30, 31, 32: Photoelectric elements
[0047] 110: First electrode 150: Second electrode
[0048] 120: Hole transport region 140: Electron transport region
[0049] 130: Light-emitting layer 135: Photoactive layer
[0050] 131: First layer 132: Second layer
[0051] 133: Third layer DETAILED DESCRIPTION
[0052] According to one aspect of the present invention, an organic compound is provided.
[0053] The organic compound is represented by the following Chemical Formula 1:
[0054] <Chemical Formula 1>
[0055]
[0056] In Chemical Formula 1,
[0057] Ar3 is a C1-C 60 heteroarylene or a divalent non-aromatic heterocyclic condensed polycyclic group,
[0058] n3 is an integer from 1 to 3,
[0059] L1 is a C3-C unsubstituted or substituted with at least one R1 60A carbocyclic group which is unsubstituted or substituted by at least one R1, or a C1-C 60 heterocyclic group,
[0060] L2 is a C3-C carbocyclic group which is unsubstituted or substituted by at least one R2, or a C1-C 60 heterocyclic group which is unsubstituted or substituted by at least one R2, 60
[0061] n1 and n2 are each independently an integer from 1 to 3,
[0062] CY1 and CY2 are each independently a C3-C carbocyclic group or a C1-C 60 heterocyclic group, 60
[0063] X 11 and X 12 are each independently C(R 41 )(R 42 ), Si(R 41 )(R 42 ), N(R 41 ), P(R 41 ), O, S, C(R 41 ), Si(R 41 ), N, P, C(=O), C(=S) or C=C(R 43 )(R 44 ),
[0064] X 11 and X 12 at least one of which is C(=O), C(=S) or C=C(R 43 )(R 44 ),
[0065] X 21 and X 22 are each independently C(R 51 )(R 52 ), Si(R 51 )(R 52 ), N(R 51 ), P(R 51 ), O, S, C(R 51 ), Si(R 51 ), N, P, C(=O), C(=S) or C=C(R 53 )(R 54 ),
[0066] X 21 and X 22 at least one of which is C(=O), C(=S) or C=C(R53 )(R 54 ),
[0067] a3, a4 and a5 are each independently an integer from 0 to 10,
[0068] R1 to R5, R 41 、R 42 、R 51 and R 52 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, 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 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted by at least one R 10a Substituted C6-C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 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 C2-C 60 heteroarylalkyl, -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),
[0069] R 43 、R 44 、R 53 and R 54 are independently electron-accepting groups.
[0070] The electron-withdrawing group is -F, -Cl, -Br, -I, cyano, nitro, -C(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2) or -B(Q1)(Q2); or a first group substituted by at least one selected from -F, -Cl, -Br, -I, -CF3, -CF2H, -CFH2, cyano, nitro, -C(=O)(Q 31 ), -S(=O)2(Q 31 ), -P(=O)(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), and,
[0071] the first group is selected from the following groups:
[0072] C1-C 20 alkyl, C2-C 20 alkenyl, C2-C 20 alkynyl and C1-C 20 alkoxy;
[0073] substituted by at least one selected from deuterium, -CD3, -CD2H, -CDH2, hydroxyl, amidino, hydrazino, hydrazono, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridyl, pyrimidinyl, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), -P(=O)(Q 31 )(Q 32 ) of a C1-C 20 alkyl, C2-C 20 alkenyl, C2-C 20 alkynyl and C1-C 20 alkoxy;
[0074] cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, a radical, pyrrolyl, phenylthio, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuryl, benzophenylthio, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuryl, dibenzophenylthio, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl and imidazopyrimidinyl; and
[0075] selected from deuterium, -CD3, -CD2H, -CDH2, hydroxy, amidino, hydrazino, hydrazono, C1-C 20 alkyl, C2-C 20 alkenyl, C2-C 20 alkynyl, C1-C 20 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, a radical, pyrrolyl, phenylthio, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuryl, benzophenylthio, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuryl, dibenzophenylthio, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidinyl, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), and -P(=O)(Q 31 )(Q 32 ), a cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, at least one substituted a radical, pyrrolyl, phenylthio, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuryl, benzophenylthio, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuryl, dibenzophenylthio, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, and imidazopyrimidinyl.
[0076] R in the chemical formula 1 10a is
[0077] deuterium (-D), -F, -Cl, -Br, -I, hydroxy, cyano, or nitro;
[0078] unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl, C2-C 60 heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 ), -N(Q 11 )(Q 12 ), -B(Q 11 )(Q 12 ), -C(=O)(Q 11 ), -S(=O)2(Q 11 ), -P(=O)(Q 11 )(Q 12 ), or any combination thereof, substituted C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, or C1-C 60 alkoxy;
[0079] unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl, C2-C 60 heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof substituted C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl or C2-C 60 heteroaralkyl; or
[0080] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ),
[0081] Q1 to Q3, Q 11 to Q 13 、Q 21 to Q 23 and Q 31 to Q 33 are each independently
[0082] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy or
[0083] unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 alkyl, C1-C60 C3-C substituted with an alkoxy group, a phenyl group, a biphenyl group, or any combination thereof 60 carbocyclic group, C1-C 60 heterocyclic group, C7-C 60 aralkyl or C2-C 60 heteroaralkyl.
[0084] According to one example, the energy level of the highest occupied molecular orbital (HOMO) of the organic compound may be from -5.8 eV to -5.0 eV, and the energy level of the lowest unoccupied molecular orbital (LUMO) of the organic compound may be from -3.9 eV to -2.7 eV.
[0085] According to one example, the organic compound may absorb visible light. For example, the organic compound may absorb green light and / or red light. For example, the maximum absorption wavelength of the organic compound may be from 490 nm to 750 nm. For example, the maximum absorption wavelength of the organic compound may be from 490 nm to 570 nm. For example, it may be from 500 nm to 560 nm. For example, it may be from 510 nm to 550 nm. For example, the maximum absorption wavelength of the organic compound may be from 570 nm to 750 nm. For example, it may be from 570 nm to 700 nm. For example, it may be from 600 nm to 680 nm.
[0086] According to one example, the organic compound may substantially not emit light. For example, the organic compound may be a substantially non-luminescent compound.
[0087] According to one example, the organic compound may be represented by the following Chemical Formula 1-1:
[0088] <Chemical Formula 1-1>
[0089]
[0090] In the Chemical Formula 1-1,
[0091] Regarding the descriptions of Ar3, n3, CY1, CY2, X 11 , X 12 , X 21 , X 22 , a3, a4, a5, and R1 to R5 are the same as those described in this specification respectively,
[0092] Y1 and Y2 are each independently C(R6)(R7), Si(R6)(R7), N(R6), P(R6), O, or S,
[0093] a1 and a2 are each independently an integer from 0 to 2,
[0094] R6 and R7 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted by at least one R 10a substituted C1-C 60 alkyl, unsubstituted or substituted by at least one R 10a substituted C2-C 60 alkenyl, unsubstituted or substituted by at least one R 10a substituted C2-C 60 alkynyl, unsubstituted or substituted by at least one R 10a substituted C1-C 60 alkoxy, unsubstituted or substituted by at least one R 10a substituted C3-C 60 carbocyclic group, unsubstituted or substituted by at least one R 10a substituted C1-C 60 heterocyclic group, unsubstituted or substituted by at least one R 10a substituted C6-C 60 aryloxy, unsubstituted or substituted by at least one R 10a substituted C6-C 60 arylthio, unsubstituted or substituted by at least one R 10a substituted C7-C 60 aralkyl, unsubstituted or substituted by at least one R 10a substituted C2-C 60 heteroaralkyl, -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).
[0095] According to one example, the organic compound can be represented by the following Chemical Formula 1-2:
[0096] <Chemical Formula 1-2>
[0097]
[0098] In the Chemical Formula 1-2,
[0099] Regarding Ar3, n3, CY1, CY2, X 11 , X 12 , X 21 , X 22 , a3, a4, a5, Y1, Y2 and R3 to R7 are the same as those described in this specification respectively,
[0100] Regarding R 11 and R 12For the descriptions of R1, please refer to the descriptions of R1 in this specification respectively.
[0101] For R 21 and R 22 For the descriptions of R2, please refer to the descriptions of R2 in this specification respectively.
[0102] According to an example, in the Chemical Formula 1, Chemical Formula 1-1 and Chemical Formula 1-2,
[0103] R 43 、R 44 、R 53 and R 54 can be, independently of each other, -F, -Cl, -Br, -I, cyano, nitro, -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2).
[0104] According to an example, in the Chemical Formula 1, Chemical Formula 1-1 and Chemical Formula 1-2,
[0105] The group represented by can be a group selected from the following Chemical Formula 1A to Chemical Formula 1K:
[0106]
[0107] In the Chemical Formula 1A to 1K,
[0108] Ar 11 and Ar 12 are, independently of each other, a C3-C 30 carbocyclic group or a C1-C 30 heterocyclic group.
[0109] X 13 、X 14 and X 15 are, independently of each other, C(R 45 )(R 46 ), Si(R 45 )(R 46 ), N(R 45 ), P(R 45 ), O, S, C(R 45 ), Si(R 45 ), N, P, C(=O), C(=S) or C=C(R 43 )(R 44 ).
[0110] For X 11 、X 12 、R4, a4, R 43 and R 44The descriptions are the same as those described in this specification respectively,
[0111] For R 45 and R 46 The descriptions are respectively referred to the description of R4 in this specification.
[0112] * is the bonding position with the adjacent atom.
[0113] According to one example, Ar in the chemical formula 1A to the chemical formula 1K 11 and Ar 12 can be independently of each other a benzene group, a pyridine group, a pyrimidine group, a triazine group, a naphthalene group, an anthracene group, a phenanthrene group, a phenalenyl group, a thiophene group, a furan group, a benzothiophene group, a benzofuran group, a dibenzothiophene group or a dibenzofuran group.
[0114] According to one example, when the group represented by in the chemical formula 1, the chemical formula 1-1 and the chemical formula 1-2 is the chemical formula 1E, the chemical formula 1E can be selected from the following chemical formula 1E-1 to the chemical formula 1E-16:
[0115]
[0116] Among the chemical formula 1E-1 to 1E-16,
[0117] For X 11 and X 12 The descriptions are the same as those described in this specification respectively.
[0118] For R 401 to R 404 and R 411 to R 418 The descriptions are respectively referred to the description of R4 in this specification.
[0119] * is the bonding position with the adjacent atom.
[0120] According to one example, when the group represented by in the chemical formula 1, the chemical formula 1-1 and the chemical formula 1-2 is the chemical formula 1F to 1J, two or more of X 11 , X 12 and X 15 can be C(=O), C(=S) or C=C(R 43 )(R 44 ).
[0121] According to one example, the one represented by The group represented can be a group selected from the following chemical formulas 2A to 2K:
[0122]
[0123] Among the said chemical formulas 2A to 2K,
[0124] Ar 21 and Ar 22 are each independently a C3-C 30 carbocyclic group or a C1-C 30 heterocyclic group,
[0125] X 23 、X 24 and X 25 are each independently C(R 55 )(R 56 ), Si(R 55 )(R 56 ), N(R 55 ), P(R 55 ), O, S, C(R 55 ), Si(R 55 ), N, P, C(=O), C(=S) or C=C(R 53 )(R 54 ),
[0126] For X 21 、X 22 、R5, a5, R 53 and R 54 the descriptions are the same as those described in this specification respectively,
[0127] For R 55 and R 56 the descriptions refer to the descriptions of R5 in this specification respectively,
[0128] * is the bonding site with the adjacent atom.
[0129] According to an example, Ar 21 and Ar 22 in the said chemical formulas 1A to 1K can each independently be a benzene group, a pyridine group, a pyrimidine group, a triazine group, a naphthalene group, an anthracene group, a phenanthrene group, a phenalene group, a thiophene group, a furan group, a benzothiophene group, a benzofuran group, a dibenzothiophene group or a dibenzofuran group.
[0130] According to an example, when the group represented by in the said chemical formulas 1, 1-1 and 1-2 is the said chemical formula 2E, the chemical formula 2E can be selected from the following chemical formulas 2E-1 to 2E-16:
[0131]
[0132] In the chemical formulas 2E-1 to 2E-16,
[0133] Regarding X 21 and X 22 the descriptions are the same as those described in this specification,
[0134] Regarding R 501 to R 504 and R 511 to R 518 the descriptions respectively refer to the description of R5 in this specification,
[0135] * is the bonding site with an adjacent atom.
[0136] According to an example, when the group represented by in the chemical formulas 1, 1-1, and 1-2 is the chemical formulas 2F to 2J, X 21 , X 22 and X 25 more than two of them can be C(=O), C(=S), or C=C(R 53 )(R 54 ).
[0137] According to an example, in the chemical formulas 1-1 and 1-2, Y1 and Y2 can each independently be N(R6), P(R6), O, or S.
[0138] According to an example, the group represented by in the chemical formulas 1, 1-1, and 1-2 can be a group selected from the following chemical formulas 3A to 3D:
[0139]
[0140] In the chemical formulas 3A to 3D,
[0141] Ar 31 is a C3-C 30 carbocyclic group or a C1-C 30 heterocyclic group,
[0142] Y 31 and Y 32 each independently are N(R 31 ), P(R 31 ), O, or S,
[0143] X 31 is C(R 31 )(R32 )), Si(R 31 )(R 32 ), N(R 31 ), P(R 31 ), O or S,
[0144] a3’ is an integer from 0 to 8,
[0145] The description for R3 is the same as that described in this specification,
[0146] For R 31 to R 34 , the descriptions respectively refer to the description for R3 in this specification,
[0147] * and *’ are bonding positions with adjacent atoms.
[0148] According to an example, Ar in the chemical formulas 3A to 3D 31 can be a benzene group, a pyridine group, a pyrimidine group, a triazine group, a naphthalene group, an anthracene group, a phenanthrene group, a phenalene group, a thiophene group, a furan group, a benzothiophene group, a benzofuran group, a dibenzothiophene group or a dibenzofuran group.
[0149] According to an example, the chemical formula 3D can be the following chemical formula 3D-1:
[0150]
[0151] In the chemical formula 3D-1,
[0152] For Y 31 , Y 32 , R 33 and R 34 , the descriptions are respectively the same as those described in this specification,
[0153] For R 35 and R 36 , the descriptions respectively refer to the description for R3 in this specification,
[0154] * and *’ are bonding positions with adjacent atoms.
[0155] According to an example, Y in the chemical formulas 3A to 3D 31 and Y 32 can be independently O or S from each other.
[0156] According to an example, in the chemical formula 1, the chemical formula 1-1 and the chemical formula 1-2, n3 can be 1 or 2.
[0157] According to an example, in the chemical formula 1,
[0158] R1 to R5, R 41 , R 42 , R 51 and R 52 can each independently be
[0159] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted by at least one R 10a substituted C1-C 20 alkyl, unsubstituted or substituted by at least one R 10a substituted C1-C 20 alkenyl, unsubstituted or substituted by at least one R 10a substituted C1-C 20 alkynyl, unsubstituted or substituted by at least one R 10a substituted C3-C 30 carbocyclic group, unsubstituted or substituted by at least one R 10a substituted C1-C 30 heterocyclic group, -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).
[0160] According to one example, the group represented by in Formula 1; and the group represented by in Formula 1 can be the same as each other.
[0161] According to one example, the organic compound can be any one of the following compounds P1 to P55:
[0162]
[0163]
[0164]
[0165]
[0166]
[0167]
[0168]
[0169] The organic compound represented by Formula 1 can be obtained by including an electron-donating group represented by , an electron-donating group represented by and It has a highest occupied molecular orbital (HOMO) energy level of -5.0 eV to -5.8 eV and a lowest unoccupied molecular orbital (LUMO) energy level of -3.9 eV to -2.7 eV by means of an electron-withdrawing group represented, and a conjugation group of an appropriate length between the electron-donating group and the electron-withdrawing group, so as to effectively absorb green light and / or red light. Therefore, it can be applied as a p-type semiconductor compound for optoelectronic devices.
[0170] In addition, the organic compound represented by Chemical Formula 1 can reduce the vibrational energy of the organic compound itself by including deuterium in the vinyl group. According to the reduction of the vibrational energy of the molecule, intermolecular reactions can be minimized, and it has excellent evaporation stability and heat resistance.
[0171] Since the purity of the photoactive layer (for example, the first layer) formed by evaporating the organic compound is excellent, the optoelectronic device including the organic compound can have excellent external quantum efficiency and excellent dark current density. For example, an optoelectronic device with high external quantum efficiency and low dark current density can be achieved by including the organic compound represented by Chemical Formula 1 as a p-type semiconductor compound in the photoactive layer.
[0172] Those skilled in the art can understand the synthesis method of the organic compound represented by Chemical Formula 1 by referring to the examples described below.
[0173] According to another aspect, there is provided an optoelectronic device, including: a first electrode; a second electrode facing the first electrode; and a photoactive layer disposed between the first electrode and the second electrode, including one or more of the above organic compounds (hereinafter, the same as the first compound).
[0174] According to an example, the optoelectronic device may further include a hole transport region disposed between the first electrode and the photoactive layer and an electron transport region disposed between the photoactive layer and the second electrode. The hole transport region may include a hole injection layer, a hole transport layer, a light emission assisting layer, an electron blocking layer, or any combination thereof. The electron transport region may include a buffer layer, a hole blocking layer, an electron adjusting layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0175] According to an example, the optoelectronic device may further include a second compound represented by any one of the following Chemical Formulas 2-1 to 2-6:
[0176]
[0177] Among Chemical Formulas 2-1 to 2-6,
[0178] Y 41 and Y42 Each independently is C(Z 51 )(Z 52 ), Si(Z 51 )(Z 52 ), N(Z 51 ), P(Z 51 ), O, S, C(=O), C(=S) or C=C(Z 51 )(Z 52 ),
[0179] Z 41 to Z 48 , Z 51 and Z 52 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted by at least one R 10a substituted C1-C 60 alkyl, unsubstituted or substituted by at least one R 10a substituted C2-C 60 alkenyl, unsubstituted or substituted by at least one R 10a substituted C2-C 60 alkynyl, unsubstituted or substituted by at least one R 10a substituted C1-C 60 alkoxy, unsubstituted or substituted by at least one R 10a substituted C3-C 60 carbocyclic group, unsubstituted or substituted by at least one R 10a substituted C1-C 60 heterocyclic group, unsubstituted or substituted by at least one R 10a substituted C6-C 60 aryloxy, unsubstituted or substituted by at least one R 10a substituted C6-C 60 arylthio, unsubstituted or substituted by at least one R 10a substituted C7-C 60 aralkyl, unsubstituted or substituted by at least one R 10a substituted C2-C 60 heteroaralkyl, -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),
[0180] R 10a , Q1 to Q3, Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q33 The same as those described in this specification respectively.
[0181] According to one example, the photoactive layer may not include fullerene-based compounds and subphthalocyanine-based compounds. For example, the photoactive layer may not include the following fullerene 60, fullerene 70, SubPC, and SubNC:
[0182]
[0183] That is, the first compound may not be the fullerene 60 and the fullerene 70. The second compound may not be the SubPC and the SubNC.
[0184] According to one example, in Chemical Formulas 2-1 to 2-6,
[0185] Z 51 and Z 52 may each independently be an unsubstituted or deuterium, -F, -Cl, -Br, -I, cyano, C1-C 60 alkyl, C1-C 60 alkoxy, or any combination thereof-substituted C1-C 60 alkyl, C3-C 10 cycloalkyl, C6-C 60 aryl, or C1-C 60 heteroaryl.
[0186] According to one example, the second compound may be any one of the following compounds N1 to N43:
[0187]
[0188]
[0189]
[0190]
[0191] According to one example, the photoactive layer may include the first compound. The photoactive layer may further include the second compound. For example, the photoactive layer may include the first compound and the second compound. The photoactive layer may include a mixture of the first compound and the second compound.
[0192] The photoactive layer may be a single layer. That is, the first compound and the second compound may exist in a mixed state in the photoactive layer.
[0193] According to an example, the photoactive layer may include a first layer adjacent to the first electrode and a second layer adjacent to the second electrode. For example, the first layer may be disposed between the first electrode and the second layer. The first layer may be disposed between the hole transport region and the second layer. The second layer may be disposed between the first layer and the second electrode. The second layer may be disposed between the first layer and the electron transport region.
[0194] According to an example, the first layer may include the first compound. The first layer may not include the second compound.
[0195] According to an example, the second layer may include the second compound. The second layer may not include the first compound.
[0196] That is, the photoactive layer may have a two-layer structure divided into the first layer including the first compound and the second layer including the second compound. That is, the first compound and the second compound may exist in an unmixed state in the photoactive layer.
[0197] According to yet another example, the photoactive layer may further include a third layer disposed between the first layer and the second layer. The third layer may include the first compound and the second compound. The third layer may include a mixture of the first compound and the second compound. That is, the first compound and the second compound may exist in a mixed state in the third layer. For example, the photoactive layer may have a three-layer structure divided into i) the first layer including the first compound and not including the second compound, ii) the third layer including all of the first compound and the second compound, and iii) the second layer including the second compound and not including the first compound.
[0198] According to another aspect, there is provided an electronic device including: the optoelectronic element; a light-emitting element that does not overlap with the optoelectronic element; and a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof.
[0199] According to an example, the light-emitting element may include a light-emitting layer.
[0200] According to yet another aspect, there is provided an electronic device including the optoelectronic element,
[0201] The electronic device is one of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, indoor or outdoor lighting and / or signal lights, a head-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a 3D display, a virtual reality or augmented reality display, a vehicle, a video wall including multiple displays tiled together, a theater or stadium screen, a light therapy device, a plaque, an automotive sensor, a home sensor, and a solar cell.
[0202] [Regarding Figure 1 and the description of 2]
[0203] Figure 1 FIG. is a diagram schematically showing a photoelectric element 30 according to an example of the present invention. The photoelectric element 30 may include a first electrode 110, a hole transport region 120, a photoactive layer 135, an electron transport region 140, and a second electrode 150.
[0204] Figure 2 FIG. is a diagram schematically showing a light-emitting element 10. The light-emitting element 10 may include a first electrode 110, a hole transport region 120, a light-emitting layer 130, an electron transport region 140, and a second electrode 150.
[0205] As an example, each of the first electrode 110, the hole transport region 120, the electron transport region 140, and the second electrode 150 of the photoelectric element 30 may substantially have one body with each of the first electrode 110, the hole transport region 120, the electron transport region 140, and the second electrode 150 of the light-emitting element 10. As another example, each of the first electrode 110, the hole transport region 120, the electron transport region 140, and the second electrode 150 of the photoelectric element 30 may be separated from each of the first electrode 110, the hole transport region 120, the electron transport region 140, and the second electrode 150 of the light-emitting element 10, but include substantially the same substances and be formed substantially simultaneously.
[0206] Hereinafter, with reference to Figure 1 and FIG. 2, the structures and manufacturing methods of the photoelectric element 30 and the light-emitting element 10 according to an example of the present invention are as follows.
[0207] [First electrode 110]
[0208] In Figure 1A substrate may be additionally disposed below the first electrode 110 or above the second electrode 150. As the substrate, a glass substrate or a plastic substrate may be used. The substrate may be a flexible substrate. For example, the substrate may include a plastic having excellent heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.
[0209] The first electrode 110, for example, may be formed by providing a first electrode material above the substrate using an evaporation method, a sputtering method, or the like. When the first electrode 110 is an anode, a high work function material that is easy to inject holes may be used as the first electrode material.
[0210] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. To form the transmissive electrode, i.e., the first electrode 110, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof may be used as the first electrode material. Alternatively, to form the semi-transmissive electrode or the reflective electrode, i.e., the first electrode 110, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof may be used as the first electrode material.
[0211] The first electrode 110 may have a single-layer structure consisting of a single layer or a multi-layer structure including multiple layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO.
[0212] [Hole transport region 120]
[0213] The hole transport region 120 may have i) a single-layer structure consisting of a single layer composed of a single substance, ii) a single-layer structure composed of a single layer including multiple different substances, or iii) a multi-layer structure including multiple layers containing multiple different substances.
[0214] The hole transport region 120 may include a hole injection layer, a hole transport layer, a light emission assisting layer, an electron blocking layer, or any combination thereof.
[0215] For example, the hole transport region 120 may have a multilayer structure of a hole injection layer / hole transport layer, a hole injection layer / hole transport layer / luminescence assisting layer, a hole injection layer / luminescence assisting layer, a hole transport layer / luminescence assisting layer, or a hole injection layer / hole transport layer / electron blocking layer laminated in sequence from the first electrode 110.
[0216] The hole transport region 120 may include a compound represented by the following Chemical Formula 201, a compound represented by the following Chemical Formula 202, or any combination thereof:
[0217] <Chemical Formula 201>
[0218]
[0219] <Chemical Formula 202>
[0220]
[0221] In Chemical Formulas 201 and 202,
[0222] L 201 to L 204 are each independently an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,
[0223] L 205 is *-O-*’, *-S-*’, *-N(Q 201 )-*’, an unsubstituted or at least one R 10a substituted C1-C 20 alkylene, an unsubstituted or at least one R 10a substituted C2-C 20 alkenylene, an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,
[0224] xa1 to xa4 are each independently one of the integers from 0 to 5,
[0225] xa5 is one of the integers from 1 to 10,
[0226] R 201 to R204 and Q 201 are each independently an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,
[0227] R 201 and R 202 are optionally connected to each other by a single bond, an unsubstituted or at least one R 10a substituted C1-C5 alkylene group or an unsubstituted or at least one R 10a substituted C2-C5 alkenylene group to form an unsubstituted or at least one R 10a substituted C8-C 60 polycyclic group (e.g., a carbazole group, etc.) (e.g., refer to the following compound HT16, etc.),
[0228] R 203 and R 204 are optionally connected to each other by a single bond, an unsubstituted or at least one R 10a substituted C1-C5 alkylene group or an unsubstituted or at least one R 10a substituted C2-C5 alkenylene group to form an unsubstituted or at least one R 10a substituted C8-C 60 polycyclic group,
[0229] na1 is one of the integers from 1 to 4.
[0230] For example, each of the chemical formulas 201 and 202 may include at least one of the groups represented by the following chemical formulas CY201 to CY217:
[0231]
[0232] In the chemical formulas CY201 to CY217, for R 10b and R 10c , the descriptions thereof refer to the description of R 10a in this specification respectively. The rings CY201 to CY204 are each independently a C3-C 20 carbocyclic group or a C1-C 20 heterocyclic group. At least one hydrogen in the chemical formulas CY201 to CY217 may be unsubstituted or substituted by R 10a as described in this specification.
[0233] According to one example, the ring CY in the chemical formulas CY201 to CY217 201 to the ring CY 204 can independently of one another be a benzene group, a naphthalene group, a phenanthrene group, or an anthracene group.
[0234] According to another example, each of the chemical formulas 201 and 202 can include at least one of the groups represented by the chemical formulas CY201 to CY203.
[0235] According to yet another example, the chemical formula 201 can include each of at least one of the groups represented by the chemical formulas CY201 to CY203 and at least one of the groups represented by the chemical formulas CY204 to CY217.
[0236] According to yet another example, it can be that xa1 in the chemical formula 201 is 1, R 201 is a group represented by one of the chemical formulas CY201 to CY203, xa2 is 0, and R 202 is a group represented by one of the chemical formulas CY204 to CY207.
[0237] According to yet another example, each of the chemical formulas 201 and 202 can not include the groups represented by the chemical formulas CY201 to CY203.
[0238] According to yet another example, each of the chemical formulas 201 and 202 can not include the groups represented by the chemical formulas CY201 to CY203 and can include at least one of the groups represented by the chemical formulas CY204 to CY217.
[0239] As yet another example, each of the chemical formulas 201 and 202 can not include the groups represented by the chemical formulas CY201 to CY217.
[0240] For example, the hole transport region 120 may include one of the following compounds HT1 to HT46, m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated-NPB, TAPC, HMTPD, TCTA (4,4',4”-tris(N-carbazolyl)triphenylamine), PANI / DBSA (Polyaniline / Dodecylbenzenesulfonic acid), PEDOT / PSS (Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate)), PANI / CSA (Polyaniline / Camphor sulfonic acid), PANI / PSS (Polyaniline / Poly(4-styrenesulfonate)), or any combination thereof:
[0241]
[0242]
[0243]
[0244]
[0245]
[0246] The thickness of the hole transport region 120 may be about to about For example, about to about When the hole transport region 120 includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer may be about to about For example, about to about The thickness of the hole transport layer may be about to about For example, about to about When the thicknesses of the hole transport region 120, the hole injection layer, and the hole transport layer satisfy the ranges described above, hole transport characteristics of a satisfactory level can be obtained without a substantial increase in the driving voltage.
[0247] The light emission assisting layer is a layer that functions to compensate for the optical resonance distance caused by the wavelength of light emitted from the light emitting layer to improve the light emission efficiency, and the electron blocking layer is a layer that functions to prevent electrons from leaking from the light emitting layer to the hole transport region 120. Substances that may be included in the hole transport region 120 described above may be included in the light emission assisting layer and the electron blocking layer.
[0248] [p-dopant]
[0249] In addition to the substances described above, the hole transport region 120 may include a charge-generation substance in order to improve conductivity. The charge-generation substance may be dispersed uniformly or non-uniformly (for example, in the form of a single layer consisting of the charge-generation substance) within the hole transport region 120.
[0250] The charge-generation substance may be, for example, a p-dopant.
[0251] For example, the LUMO energy level of the p-dopant may be -3.5 eV or less.
[0252] According to one example, the p-dopant may include a quinone derivative, a cyano-containing compound, a compound containing element EL1 and element EL2, or any combination thereof.
[0253] Examples of the quinone derivative may include TCNQ, F4-TCNQ, etc.
[0254] Examples of the cyano-containing compound may include HAT-CN, a compound represented by the following Chemical Formula 221, etc.
[0255]
[0256] <Chemical Formula 221>
[0257]
[0258] In Chemical Formula 221,
[0259] R 221 to R 223 are each independently an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C60 A heterocyclic group,
[0260] wherein at least one of said R 221 to R 223 is independently of one another cyano; -F; -Cl; -Br; -I; a C1-C 20 alkyl group substituted by cyano, -F, -Cl, -Br, -I or any combination thereof; or a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group.
[0261] In the compound containing element EL1 and element EL2, element EL1 may be a metal, a metalloid or a combination thereof, and element EL2 may be a non-metal, a metalloid or a combination thereof.
[0262] Examples of said metal 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.); lanthanide metals (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.), etc.
[0263] Examples of said metalloid may include silicon (Si), antimony (Sb), tellurium (Te), etc.
[0264] Examples of said non-metal may include oxygen (O), halogens (e.g., F, Cl, Br, I, etc.), etc.
[0265] For example, the compound containing element EL1 and element EL2 may include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides, metal iodides, etc.), metalloid halides (e.g., metalloid fluorides, metalloid chlorides, metalloid bromides, metalloid iodides, etc.), metal tellurides or any combination thereof.
[0266] Examples of the metal oxide may include tungsten oxides (e.g., WO, W2O3, WO2, WO3, W2O5, etc.), vanadium oxides (e.g., VO, V2O3, VO2, V2O5, etc.), molybdenum oxides (e.g., MoO, Mo2O3, MoO2, MoO3, Mo2O5, etc.), rhenium oxides (e.g., ReO3, etc.), etc.
[0267] Examples of the metal halide may include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, lanthanide metal halides, etc.
[0268] Examples of the alkali metal halide may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, CsI, etc.
[0269] Examples of the alkaline earth metal halide may include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, BaI2, etc.
[0270] Examples of the transition metal halides may include titanium halides (e.g., TiF4, TiCl4, TiBr4, TiI4, etc.), zirconium halides (e.g., ZrF4, ZrCl4, ZrBr4, ZrI4, etc.), hafnium halides (e.g., HfF4, HfCl4, HfBr4, HfI4, etc.), vanadium halides (e.g., VF3, VCl3, VBr3, VI3, etc.), niobium halides (e.g., NbF3, NbCl3, NbBr3, NbI3, etc.), tantalum halides (e.g., TaF3, TaCl3, TaBr3, 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, ReI2, etc.), iron halides (e.g., FeF2, FeCl2, FeBr2, FeI2, etc.), ruthenium halides (e.g., RuF2, RuCl2, RuBr2, RuI2, etc.), osmium halides (e.g., OsF2, OsCl2, OsBr2, OsI2, etc.), cobalt halides (e.g., CoF2, CoCl2, CoBr2, CoI2, etc.), rhodium halides (e.g., RhF2, RhCl2, RhBr2, RhI2, etc.), iridium halides (e.g., IrF2, IrCl2, IrBr2, IrI2, etc.), nickel halides (e.g., NiF2, NiCl2, NiBr2, NiI2, etc.), palladium halides (e.g., PdF2, PdCl2, PdBr2, PdI2, etc.), platinum halides (e.g., PtF2, PtCl2, PtBr2, PtI2, etc.), copper halides (e.g., CuF, CuCl, CuBr, CuI, etc.), silver halides (e.g., AgF, AgCl, AgBr, AgI, etc.), gold halides (e.g., AuF, AuCl, AuBr, AuI, etc.), etc.
[0271] Examples of the post-transition metal halides may include zinc halides (e.g., ZnF2, ZnCl2, ZnBr2, ZnI2, etc.), indium halides (e.g., InI3, etc.), tin halides (e.g., SnI2, etc.), etc.
[0272] Examples of the lanthanide metal halides may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, SmI3, etc.
[0273] Examples of the metalloid halide may include antimony halide (eg, SbCl5, etc.).
[0274] Examples of the metal tellurides may include alkali metal tellurides (e.g., Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metal tellurides (e.g., TiTe2, ZrTe2, HfTe2, V2Te3, Nb2Te3, Ta2Te3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe, Au2Te, etc.), late transition metal tellurides (for example, ZnTe, etc.), lanthanide metal tellurides (for example, LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.), etc.
[0275] [Light-emitting layer 130]
[0276] The light-emitting element 10 may include a light-emitting layer 130 disposed above the hole transport region 120 .
[0277] The light-emitting layer 130 may include, in addition to various organic substances, metal-containing compounds such as organometallic compounds, inorganic substances such as quantum dots, and the like.
[0278] On the other hand, the light-emitting layer 130 may include i) two or more light-emitting units stacked sequentially between the first electrode 110 and the second electrode 150, and ii) a charge generation layer disposed between the two light-emitting units. When the light-emitting layer 130 includes the light-emitting units and the charge generation layer as described above, the light-emitting element 10 may be a tandem light-emitting element.
[0279] When the light-emitting element 10 is a full-color light-emitting element, the light-emitting layer 130 can be patterned into a red light-emitting layer, a green light-emitting layer, and / or a blue light-emitting layer for each sub-pixel. Alternatively, the light-emitting layer 130 can have a structure in which two or more of the red light-emitting layer, the green light-emitting layer, and the blue light-emitting layer are in contact or stacked separately, or a structure in which two or more of the red light-emitting material, the green light-emitting material, and the blue light-emitting material are mixed without separation, thereby emitting white light.
[0280] The light-emitting layer 130 may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.
[0281] The content of the dopant in the light-emitting layer 130 may be about 0.01 to about 15 parts by weight relative to 100 parts by weight of the host.
[0282] Alternatively, the light-emitting layer 130 may include quantum dots.
[0283] On the other hand, the light-emitting layer 130 may include a delayed fluorescence material. The delayed fluorescence material may function as the host or the dopant in the light-emitting layer 130.
[0284] The thickness of the light-emitting layer 130 may be about to about For example, about to about When the thickness of the light-emitting layer 130 satisfies the above-described range, excellent light-emitting characteristics can be exhibited without a substantial increase in the driving voltage.
[0285] [Host]
[0286] The host may include a compound represented by the following Chemical Formula 301:
[0287] <Chemical Formula 301>
[0288] [Ar 301 xb11 -[(L 301 ) xb1 -R 301 xb21
[0289] In the Chemical Formula 301,
[0290] Ar 301 and L 301 are each independently an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,
[0291] xb11 is 1, 2, or 3,
[0292] xb1 is one of the integers from 0 to 5,
[0293] R 301 is hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted by at least one R 10a substituted C1-C 60 alkyl, unsubstituted or substituted by at least one R 10a substituted C2-C 60 alkenyl, unsubstituted or substituted by at least one R 10a substituted C2-C 60 alkynyl, unsubstituted or substituted by at least one R 10a substituted C1-C 60 alkoxy, unsubstituted or substituted by at least one R 10a substituted C3-C 60 carbocyclic group, unsubstituted or substituted by at least one R 10a substituted C1-C 60 heterocyclic group, -Si(Q 301 )(Q 302 )(Q 303 )、-N(Q 301 )(Q 302 )、-B(Q 301 )(Q 302 )、-C(=O)(Q 301 )、-S(=O)2(Q 301 ) or -P(=O)(Q 301 )(Q 302 ),
[0294] xb21 is one of the integers from 1 to 5,
[0295] For the description of Q 301 to Q 303 refer to the description of Q1 in this specification respectively.
[0296] For example, when xb11 in the chemical formula 301 is 2 or more, two or more Ar 301 can be connected to each other by a single bond.
[0297] As another example, the host may include a compound represented by the following chemical formula 301-1, a compound represented by the following chemical formula 301-2, or any combination thereof:
[0298] <Chemical formula 301-1>
[0299]
[0300] <Chemical formula 301-2>
[0301]
[0302] In the chemical formulas 301-1 and 301-2,
[0303] Ring A 301 to Ring A 304 are each independently an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,
[0304] X 301 is O, S, N[(L 304 ) xb4 -R 304 , C(R 304 )(R 305 ), or Si(R 304 )(R 305 ),
[0305] xb22 and xb23 are each independently 0, 1, or 2,
[0306] For the descriptions of L 301 , xb1, and R 301 , please refer to the content described in this specification respectively,
[0307] For the descriptions of L 302 to L 304 , please refer to the description of the said L 301 independently of each other,
[0308] For the descriptions of xb2 to xb4, please refer to the description of the said xb1 independently of each other,
[0309] For the descriptions of R 302 to R 305 and R 311 to R 314 , please refer to the description of the said R 301 respectively.
[0310] As yet another example, the host may include an alkaline earth metal complex, a late transition metal complex, or any combination thereof. For example, the host may include a Be complex (e.g., the following compound H55), a Mg complex, a Zn complex, or any combination thereof.
[0311] As yet another example, the host may include one of the following compounds H1 to H128, ADN (9,10 - Di(2 - naphthyl)anthracene), MADN (2 - Methyl - 9,10 - bis(naphthalen - 2 - yl)anthracene), TBADN (9,10 - di-(2 - naphthyl)-2 - t - butyl - anthracene), CBP (4,4'-bis(N - carbazolyl)-1,1'-biphenyl), mCP (1,3 - di(carbazol - 9 - yl)benzene), TCP (1,3,5 - tri(carbazol - 9 - yl)benzene) or any combination thereof:
[0312]
[0313]
[0314]
[0315]
[0316]
[0317]
[0318] [Phosphorescent dopant]
[0319] The phosphorescent dopant may include at least one transition metal as the central metal.
[0320] The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand or any combination thereof.
[0321] The phosphorescent dopant may be neutral.
[0322] For example, the phosphorescent dopant may include an organometallic compound represented by the following Chemical Formula 401:
[0323] <Chemical Formula 401>
[0324] M(L 401 )xc1 (L 402 ) xc2
[0325] <Chemical Formula 402>
[0326]
[0327] In the Chemical Formulas 401 and 402,
[0328] M is 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)),
[0329] L 401 is a ligand represented by the Chemical Formula 402, xc1 is 1, 2, or 3, and when xc1 is 2 or more, two or more Ls 401 are the same as or different from each other,
[0330] L 402 is an organic ligand, xc2 is 0, 1, 2, 3, or 4, and when xc2 is 2 or more, two or more Ls 402 are the same as or different from each other,
[0331] X 401 and X 402 are independently nitrogen or carbon,
[0332] Ring A 401 and Ring A 402 are independently a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group,
[0333] T 401 is 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=*’,
[0334] X 403 and X 404 are independently a chemical bond (e.g., a covalent bond or a coordination bond), O, S, N(Q 413 ), B(Q 413 ), P(Q 413 ), C(Q 413 )(Q414 ) or Si(Q 413 )(Q 414 ),
[0335] Regarding the description of said Q 411 to Q 414 , the description respectively refers to the description of Q1 in this specification,
[0336] R 401 and R 402 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted by at least one R 10a substituted C1-C 20 alkyl, unsubstituted or substituted by at least one R 10a substituted C1-C 20 alkoxy, unsubstituted or substituted by at least one R 10a substituted C3-C 60 carbocyclic group, unsubstituted or substituted by at least one R 10a substituted C1-C 60 heterocyclic group, -Si(Q 401 )(Q 402 )(Q 403 ), -N(Q 401 )(Q 402 ), -B(Q 401 )(Q 402 ), -C(=O)(Q 401 ), -S(=O)2(Q 401 ), or -P(=O)(Q 401 )(Q 402 ),
[0337] Regarding the description of said Q 401 to Q 403 , the description respectively refers to the description of Q1 in this specification,
[0338] xc11 and xc12 are each independently one of the integers from 0 to 10,
[0339] The * and *' in the chemical formula 402 are respectively the bonding positions with M in the chemical formula 401.
[0340] For example, it can be that i) X 401 in the chemical formula 402 is nitrogen, X 402 is carbon, or ii) X 401 and X 402 are both nitrogen.
[0341] As another example, when xc1 in the chemical formula 401 is 2 or more, two or more Ls401 Two rings A in 401 may optionally be connected to each other by a linking group, i.e., T 402 or two rings A 402 may optionally be connected to each other by a linking group, i.e., T 403 (see Compounds PD1 to PD4 and PD7 below). For the description of the said T 402 and T 403 , reference is respectively made to the description of T401 in this specification.
[0342] L in the chemical formula 401 402 may be any organic ligand. For example, the said L 402 may include a halogen group, a diketone group (e.g., acetylacetone group), a carboxylic acid group (e.g., picolinate group), -C(=O), an isonitrile group, a -CN group, a phosphorus group (e.g., phosphine group, phosphite group, etc.) or any combination thereof.
[0343] The phosphorescent dopant may, for example, include one of the following Compounds PD1 to PD39 or any combination thereof:
[0344]
[0345]
[0346]
[0347] [Fluorescent dopant]
[0348] The fluorescent dopant may include a compound containing an amine group, a compound containing a styrene group or any combination thereof.
[0349] For example, the fluorescent dopant may include a compound represented by the following chemical formula 501:
[0350] <Chemical formula 501>
[0351]
[0352] In the chemical formula 501, it may be that
[0353] Ar 501 , L 501 to L 503 , R 501 and R 502 are each independently unsubstituted or substituted by at least one R 10a substituted C3-C 60The carbocyclic group is either unsubstituted or substituted by at least one R 10a substituted C1-C 60 heterocyclic group,
[0354] xd1 to xd3 are each independently 0, 1, 2, or 3,
[0355] xd4 is 1, 2, 3, 4, 5, or 6.
[0356] For example, Ar in the chemical formula 501 501 may include a condensed ring group in which three or more monocyclic groups are condensed with each other (for example, an anthracene group, group, a pyrene group, etc.).
[0357] As another example, xd4 in the chemical formula 501 may be 2.
[0358] For example, the fluorescent dopant may include one of the following compounds FD1 to FD37, DPVBi, DPAVBi, or any combination thereof:
[0359]
[0360]
[0361]
[0362]
[0363] [Thermally activated delayed fluorescence material]
[0364] The light-emitting layer 130 may include a thermally activated delayed fluorescence material.
[0365] The thermally activated delayed fluorescence material in this specification may be selected from any compound that can release thermally activated delayed fluorescence through a thermally activated delayed fluorescence release mechanism.
[0366] The thermally activated delayed fluorescence material included in the light-emitting layer 130 may act as a host or a dopant depending on the types of other materials included in the light-emitting layer 130.
[0367] According to one example, the difference between the triplet energy level (eV) and the singlet energy level (eV) of the thermally activated delayed fluorescence material may be 0 eV or more and 0.5 eV or less. By the difference between the triplet energy level (eV) and the singlet energy level (eV) of the thermally activated delayed fluorescence material satisfying the above-described range, up-conversion from the triplet state to the singlet state in the thermally activated delayed fluorescence material can be effectively achieved, thereby improving the luminous efficiency of the light-emitting element 10, etc.
[0368] For example, the delayed fluorescent substance may include i) at least one electron donor (eg, a C3-C4-rich π-electron group such as a carbazole group); 60 Cyclic groups (πelectron-rich C3-C 60 Cyclic group) and at least one electron acceptor (e.g., sulfoxide group, cyano group, π-electron-deficient nitrogen-containing C1-C 60 Cyclic group (πelectron-deficientnitrogen-containing C1-C 60 ii) a substance comprising two or more cyclic groups condensed together while sharing boron (B); 60 Substances with polycyclic groups, etc.
[0369] Examples of the delayed fluorescent substance may include at least one of the following compounds DF1 to DF14:
[0370]
[0371]
[0372] [Quantum dot]
[0373] The light emitting layer 130 may include quantum dots.
[0374] In this specification, quantum dots refer to crystals of semiconductor compounds and may include any substance that can emit light of various wavelengths depending on the size of the crystal.
[0375] The diameter of the quantum dots may be, for example, about 1 nm to 10 nm.
[0376] The quantum dots can be synthesized by wet chemical process, organometallic chemical evaporation process, molecular beam epitaxy process or similar processes.
[0377] The wet chemical process involves mixing an organic solvent and a precursor substance to grow quantum dot particle crystals. During crystal growth, the organic solvent naturally acts as a dispersant, distributing itself across the surface of the quantum dot crystals. This process regulates crystal growth, making it easier than vapor deposition methods like metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE), allowing for controlled growth of quantum dot particles through a low-cost process.
[0378] The quantum dots may include II-VI group semiconductor compounds; III-V group semiconductor compounds; III-VI group semiconductor compounds; I-III-VI group semiconductor compounds; IV-VI group semiconductor compounds; group IV elements or compounds; or any combination thereof.
[0379] Examples of the II-VI group semiconductor compounds may include binary compounds such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS; ternary compounds such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, MgZnS; quaternary compounds such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe; or any combination thereof.
[0380] Examples of the III-V group semiconductor compounds may include binary compounds such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb; ternary compounds such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, InPSb; quaternary compounds such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb; or any combination thereof. On the other hand, the III-V group semiconductor compounds may further include group II elements. Examples of the III-V group semiconductor compounds further including group II elements may include InZnP, InGaZnP, InAlZnP, etc.
[0381] Examples of the III-VI group semiconductor compounds may include binary compounds such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3, InTe; ternary compounds such as InGaS3, InGaSe3; or any combination thereof.
[0382] Examples of the I-III-VI group semiconductor compounds may include ternary compounds such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, AgAlO2; quaternary compounds such as AgInGaS, AgInGaS2; or any combination thereof.
[0383] Examples of the IV-VI group semiconductor compounds may include binary compounds such as SnS, SnSe, SnTe, PbS, PbSe, PbTe; ternary compounds such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe; quaternary compounds such as SnPbSSe, SnPbSeTe, SnPbSTe; or any combination thereof.
[0384] Examples of the Group IV element or compound may include single elements such as Si, Ge; binary compounds such as SiC, SiGe; or any combination thereof.
[0385] Each element included in the multi-element compounds such as the binary compound, ternary compound, and quaternary compound may exist in the particles at a uniform concentration or a non-uniform concentration.
[0386] On the other hand, the quantum dots may have a single structure or a core-shell dual structure in which the concentrations of the respective elements included in the corresponding quantum dots are uniform. For example, the substance included in the core and the substance included in the shell may be different from each other.
[0387] The shell of the quantum dots may function as a protective layer for preventing chemical denaturation of the core to maintain semiconductor characteristics and / or as a charging layer for imparting electrophoretic characteristics to the quantum dots. The shell may be a single layer or a multi-layer. The interface between the core and the shell may have a concentration gradient in which the concentration of the elements present in the shell decreases as it approaches the center.
[0388] Examples of the shell of the quantum dots may include oxides of metals, metalloids or non-metals, semiconductor compounds, or combinations thereof. Examples of the oxides of metals, metalloids or non-metals may include binary compounds such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, NiO; ternary compounds such as MgAl2O4, CoFe2O4, NiFe2O4, CoMn2O4; or any combination thereof. Examples of the semiconductor compounds may include II-VI group semiconductor compounds, III-V group semiconductor compounds, III-VI group semiconductor compounds, I-III-VI group semiconductor compounds, IV-VI group semiconductor compounds, or any combination thereof as described in this specification. For example, the semiconductor compounds may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.
[0389] The quantum dots may have a full width at half maximum (FWHM) of the emission wavelength spectrum of about 45 nm or less, specifically about 40 nm or less, and more specifically about 30 nm or less. Within this range, color purity or color reproducibility can be improved. In addition, since the light emitted by such quantum dots is emitted omnidirectionally, a wide viewing angle can be improved.
[0390] In addition, the morphology of the quantum dots may specifically be spherical, pyramidal, multi-arm, or cubic nanoparticles, nanotubes, nanowires, nanofibers, nanoplatelet particles, or the like.
[0391] By adjusting the size of the quantum dots, the band gap can be adjusted, and thus light in various wavelength ranges can be obtained in the quantum dot light-emitting layer. Therefore, by using quantum dots of different sizes, a light-emitting device that emits light of various wavelengths can be realized. Specifically, the size of the quantum dots can be selected to emit red, green, and / or blue light. In addition, the sizes of the quantum dots can be configured such that light of various colors is combined to emit white light.
[0392] [Light-Active Layer 135]
[0393] The optoelectronic element 30 may include a photoactive layer 135 disposed above the hole transport region 120. The photoactive layer 135 may be disposed between the hole transport region 120 and the electron transport region 140. As an example, the photoactive layer 135 may be disposed between the hole transport layer included in the hole transport region 120 and the buffer layer included in the electron transport region 140. As another example, the photoactive layer 135 may be disposed between the light-emission assisting layer included in the hole transport region 120 and the buffer layer included in the electron transport region 140.
[0394] The photoactive layer 135 may include the first compound and the second compound. The first compound may be referred to as an electron-donor compound or a p-type compound, and the second compound may be referred to as an electron-acceptor compound or an n-type compound.
[0395] The first compound and the second compound may be mixed and included in the photoactive layer 135. For example, the photoactive layer 135 may be a single layer including the first compound and the second compound.
[0396] The photoactive layer 135 may absorb incident light to generate excitons. The excitons may generate holes and electrons. The holes generated by the photoactive layer 135 may move to the first electrode 110 through the hole transport region 120. The electrons generated by the photoactive layer 135 may move to the second electrode 150 through the electron transport region 140.
[0397] That is, the photoactive layer 135 may absorb light to generate an electrical signal. Specifically, the first compound included in the photoactive layer 135 may function as a donor that supplies electrons, and the second compound included in the photoactive layer 135 may function as an acceptor that accepts electrons. Therefore, the optoelectronic element 30 including the photoactive layer 135 may function as a photosensor. For example, the optoelectronic element 30 may function as a fingerprint recognition sensor, for which reference is made to Figure 5 described later.
[0398] [Electron transport region 140]
[0399] The electron transport region 140 may have i) a single-layer structure consisting of a single layer composed of a single substance, ii) a single-layer structure consisting of a single layer including a plurality of different substances, or iii) a multi-layer structure including a plurality of layers each including a plurality of different substances.
[0400] The electron transport region 140 may include a buffer layer, a hole blocking layer, an electron modulating layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0401] For example, the electron transport region 140 may have a structure such as an electron transport layer / electron injection layer, a hole blocking layer / electron transport layer / electron injection layer, an electron modulating layer / electron transport layer / electron injection layer, or a buffer layer / electron transport layer / electron injection layer, which are sequentially stacked from the light emitting layer 130.
[0402] The electron transport region 140 (for example, the buffer layer, the hole blocking layer, the electron modulating layer, or the electron transport layer in the electron transport region 140) may include a metal-free compound containing at least one π electron-deficient nitrogen-containing C1-C 60 Cyclic group. 60
[0403] For example, the electron transport region 140 may include a compound represented by the following Chemical Formula 601.
[0404] <Chemical Formula 601>
[0405] [Ar 601 xe11 -[(L 601 ) xe1 -R 601 xe21
[0406] In the Chemical Formula 601,
[0407] Ar 601 and L 601 are each independently an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,
[0408] xe11 is 1, 2, or 3,
[0409] xe1 is 0, 1, 2, 3, 4, or 5,
[0410] R 601 is an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group, an unsubstituted or at least one R 10a Substituted C1-C 60 heterocyclic group, -Si(Q 601 )(Q 602 )(Q 603 ), -C(=O)(Q 601 ), -S(=O)2(Q 601 ), or -P(=O)(Q 601 )(Q 602 ),
[0411] For the description of the said Q 601 to Q 603 please refer to the description of Q1 in this specification respectively.
[0412] xe21 is 1, 2, 3, 4 or 5,
[0413] The said Ar 601 , L 601 and R 601 at least one of which is independently an unsubstituted or R 10a substituted π-deficient nitrogen-containing C1-C 60 ring group.
[0414] For example, when xe11 in the said Chemical Formula 601 is 2 or more, two or more Ar 601 can be connected to each other by a single bond.
[0415] As another example, Ar in the said Chemical Formula 601 601 can be an unsubstituted or R 10a substituted anthracene group.
[0416] As yet another example, the electron transport region 140 can include a compound represented by the following Chemical Formula 601-1:
[0417] <Chemical Formula 601-1>
[0418]
[0419] In the said Chemical Formula 601-1, it can be that,
[0420] X 614 is N or C(R 614 ), X 615 is N or C(R 615 ), X 616 is N or C(R 616 ), X 614 to X 616 at least one of which is N,
[0421] For L 611 to L613 The description of [[]] respectively refers to the description of the [[]] for the [[]] 601 ,
[0422] The description of xe611 to xe613 respectively refers to the description of the xe1,
[0423] For R 611 to R 613 The description of [[]] respectively refers to the description of the [[]] for the [[]] 601 ,
[0424] R 614 to R 616 Each independently is hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 20 alkyl, C1-C 20 alkoxy, an unsubstituted or at least one R- 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R- 10a substituted C1-C 60 heterocyclic group.
[0425] For example, xe1 and xe611 to xe613 in the chemical formulas 601 and 601-1 can each independently be 0, 1, or 2.
[0426] The electron transport region 140 may include one of the following compounds ET1 to ET45, BCP (2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline; 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-Diphenyl-1,10-phenanthroline; 4,7-diphenyl-1,10-phenanthroline), Alq3, BAlq, TAZ, NTAZ, or any combination thereof:
[0427]
[0428]
[0429]
[0430]
[0431] The thickness of the electron transport region 140 may be about to about For example, about to about When the electron transport region 140 includes a buffer layer, a hole blocking layer, an electron modulating layer, an electron transport layer, or any combination thereof, it may be that the thicknesses of the buffer layer, the hole blocking layer, or the electron modulating layer are independently about to about For example, about to about The thickness of the electron transport layer is about to about For example, about to about When the thicknesses of the buffer layer, the hole blocking layer, the electron modulating layer, the electron transport layer, and / or the electron transport region 140 satisfy the ranges described above, satisfactory electron transport characteristics can be obtained without a substantial increase in the driving voltage.
[0432] The electron transport region 140 (e.g., the electron transport layer in the electron transport region 140), in addition to the materials described above, may further include a metal-containing material.
[0433] The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The metal ions of the alkali metal complex may be Li ions, Na ions, K ions, Rb ions, or Cs ions, and the metal ions of the alkaline earth metal complex may be Be ions, Mg ions, Ca ions, Sr ions, or Ba ions. The ligands assigned to the metal ions of the alkali metal complex and the alkaline earth metal complex may independently include 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.
[0434] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, the following compounds ET-D1(Liq) or ET-D2:
[0435]
[0436] The electron transport region 140 may include an electron injection layer that facilitates electron injection from the second electrode 150. The electron injection layer may be in direct contact with the second electrode 150, but is not limited thereto.
[0437] The electron injection layer may have i) a single-layer structure consisting of a single layer composed of a single substance, ii) a single-layer structure consisting of a single layer including a plurality of different substances from each other, or iii) a multi-layer structure having a plurality of layers including a plurality of different substances from each other.
[0438] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, a compound containing an alkali metal, a compound containing an alkaline earth metal, a compound containing a rare earth metal, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
[0439] The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
[0440] The compound containing an alkali metal, the compound containing an alkaline earth metal, and the compound containing a rare earth metal may include oxides, halides (e.g., fluorides, chlorides, bromides, iodides, etc.), tellurides of each of the alkali metal, the alkaline earth metal, and the rare earth metal, or any combination thereof.
[0441] The compound containing an alkali metal may include alkali metal oxides such as Li2O, Cs2O, K2O, alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, or any combination thereof. The compound containing an alkaline earth metal may include BaO, SrO, CaO, Ba x Sr 1-x O (where x is a real number satisfying 0 < x < 1), Ba x Ca 1-xAlkaline earth metal oxides such as O (where x is a real number satisfying 0 < x < 1). The rare earth metal-containing compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof. Alternatively, the rare earth metal-containing compound may include lanthanide metal tellurides. Examples of the lanthanide metal tellurides 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, Lu2Te3, etc.
[0442] The alkali metal complex, alkaline earth metal complex, and rare earth metal complex may include i) one of the ions of the alkali metal, alkaline earth metal, and rare earth metal as described above, and ii) a ligand bonded to the metal ion, such as hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
[0443] The electron injection layer may be composed only of the alkali metal, alkaline earth metal, rare earth metal, alkali metal-containing compound, alkaline earth metal-containing compound, rare earth metal-containing compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex as described above, or only of any combination thereof, or may further include an organic substance (e.g., the compound represented by Chemical Formula 601).
[0444] According to one example, the electron injection layer i) may be composed of (consist of) an alkali metal-containing compound (e.g., an alkali metal halide), or ii) composed of a) an alkali metal-containing compound (e.g., an alkali metal halide); and b) an alkali metal, alkaline earth metal, rare earth metal, or any combination thereof. For example, the electron injection layer may be a KI:Yb co-evaporated film, an RbI:Yb co-evaporated film, a LiF:Yb co-evaporated film, etc.
[0445] When the electron injection layer further includes an organic material, the alkali metal, alkaline earth metal, rare earth metal, compound containing an alkali metal, compound containing an alkaline earth metal, compound containing a rare earth metal, 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.
[0446] The thickness of the electron injection layer may be about to about about to about When the thickness of the electron injection layer satisfies the range described above, satisfactory electron injection characteristics can be obtained without a substantial increase in the driving voltage.
[0447] [Second electrode 150]
[0448] The second electrode 150 may be disposed on the electron transport region 140. The second electrode 150 may be an electron injection electrode, i.e., a cathode, but in this case, as the material for the second electrode 150, a metal, alloy, conductive compound, or any combination thereof having a low work function may be used.
[0449] 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 transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
[0450] The second electrode 150 may have a single-layer structure of a single layer or a multi-layer structure having a plurality of layers.
[0451] [Cover layer]
[0452] A first cover layer may be disposed outside the first electrode 110 and / or a second cover layer may be disposed outside the second electrode 150. Specifically, the light-emitting element 10 may have a structure in which the first cover layer, the first electrode 110, the light-emitting layer 130, and the second electrode 150 are stacked in sequence, a structure in which the first electrode 110, the light-emitting layer 130, the second electrode 150, and the second cover layer are stacked in sequence, or a structure in which the first cover layer, the first electrode 110, the light-emitting layer 130, the second electrode 150, and the second cover layer are stacked in sequence.
[0453] The light generated from the light-emitting layer 130 of the light-emitting element 10 can be emitted to the outside through the semi-transmissive electrode or the transmissive electrode, i.e., the first electrode 110 and the first cover layer, and the light generated from the light-emitting layer 130 of the light-emitting element 10 can be emitted to the outside through the semi-transmissive electrode or the transmissive electrode, i.e., the second electrode 150 and the second cover layer.
[0454] The first cover layer and the second cover layer can function to improve the external light-emitting efficiency according to the principle of constructive interference. Thereby, the light extraction efficiency of the light-emitting element 10 can be improved, and thus the light-emitting efficiency of the light-emitting element 10 can be improved.
[0455] Each of the first cover layer and the second cover layer may include a substance having a refractive index of about 1.6 or more (at about 520 nm to about 630 nm).
[0456] The first cover layer and the second cover layer may be independently an organic cover layer including an organic substance, an inorganic cover layer including an inorganic substance, or an organic-inorganic composite cover layer including an organic substance and an inorganic substance.
[0457] At least one of the first cover layer and the second cover layer may independently include a carbocyclic compound, a heterocyclic compound, a compound containing an amine group, porphine derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, alkaline earth metal complexes, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the compound containing an amine group may optionally be substituted with substituents including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. According to one example, at least one of the first cover layer and the second cover layer may independently include a compound containing an amine group.
[0458] For example, at least one of the first cover layer and the second cover layer may independently include the compound represented by Chemical Formula 201, the compound represented by Chemical Formula 202, or any combination thereof.
[0459] According to still another example, at least one of the first cover layer and the second cover layer may independently include one of the compounds HT28 to HT33, one of the following compounds CP1 to CP6, β-NPB, or any of their compounds:
[0460]
[0461] [Film]
[0462] According to another aspect, the electronic device may include a film. The film may be, for example, an optical component (or, a light control mechanism) (e.g., a color filter, a color conversion component, a cover layer, a light extraction efficiency improvement layer, a selective light absorption layer, a polarizing layer, a layer containing quantum dots, etc.), a light shielding component (e.g., a light reflection layer, a light absorption layer, etc.), a protection component (e.g., an insulating layer, a dielectric layer, etc.), and the like.
[0463] [Regarding Figure 3 the description of
[0464] Figure 3 FIG. is a diagram schematically showing a photoelectric element according to another example of the present invention.
[0465] Figure 3 The shown photoelectric element 31 is the same as and / or similar to the Figure 1 shown photoelectric element 30 except for the photoactive layer 135, and thus the description of other constituent elements is omitted.
[0466] The photoelectric element 31 may include a photoactive layer 135 disposed between a hole transport region 120 and an electron transport region 140. As an example, the photoactive layer 135 may be disposed between the hole transport layer included in the hole transport region 120 and the buffer layer included in the electron transport region 140. As another example, the photoactive layer 135 may be disposed between the light emission assisting layer included in the hole transport region 120 and the buffer layer included in the electron transport region 140.
[0467] The photoactive layer 135 may include a first layer 131 adjacent to the hole transport region 120 and a second layer 132 adjacent to the electron transport region 140. For example, the first layer 131 may be in direct contact with the second layer 132.
[0468] As an example, the first layer 131 may be in direct contact with the hole transport layer included in the hole transport region 120. As another example, the first layer 131 may be in direct contact with the light emission assisting layer disposed on the hole transport layer.
[0469] As an example, the second layer 132 may be in direct contact with the buffer layer included in the electron transport region 140.
[0470] The first layer 131 may include the first compound. The first layer 131 may be composed of the first compound. For example, the first layer 131 may not include the second compound. The first layer 131 may also be referred to as a p-type photoactive layer or a donor layer.
[0471] The second layer 132 may include the second compound. The second layer 132 may be composed of the second compound. For example, the second layer 132 may not include the first compound. The second layer 132 may also be referred to as an n-type photoactive layer or an acceptor layer.
[0472] That is, the photoactive layer 135 may have a two-layer structure divided into a first layer 131 including the first compound and a second layer 132 including the second compound.
[0473] The photoactive layer 135 may absorb incident light to form excitons. The excitons may generate holes and electrons. The holes generated by the photoactive layer 135 may move to the first electrode 110 through the hole transport region 120. The electrons generated by the photoactive layer 135 may move to the second electrode 150 through the electron transport region 140.
[0474] That is, the photoactive layer 135 may absorb light to generate an electrical signal. Specifically, the first compound included in the first layer 131 may act as a donor that supplies electrons, and the second compound included in the second layer 132 may act as an acceptor that accepts electrons. Therefore, the optoelectronic element 30 including the photoactive layer 135 may act as a photosensor. For example, the optoelectronic element 31 may act as a fingerprint recognition sensor, for which reference is made Figure 5 described below.
[0475] [Regarding the Figure 4 description of
[0476] Figure 4 is a diagram schematically showing an optoelectronic element according to still another example of the present invention.
[0477] Figure 4 The shown optoelectronic element 32 is the same as and / or similar to the Figure 3 shown optoelectronic element 31 except for the photoactive layer 135, and thus the description of other components is omitted.
[0478] The optoelectronic element 32 may include a photoactive layer 135 disposed between the hole transport region 120 and the electron transport region 140. As an example, the photoactive layer 135 may be disposed between the hole transport layer included in the hole transport region 120 and the buffer layer included in the electron transport region 140. As another example, the photoactive layer 135 may be disposed between the light emission assisting layer included in the hole transport region 120 and the buffer layer included in the electron transport region 140.
[0479] The photoactive layer 135 may include a first layer 131 adjacent to the hole transport region 120, a second layer 132 adjacent to the electron transport region 140, and a third layer 133 disposed between the first layer 131 and the second layer 132. For example, the third layer 133 may be in direct contact with the first layer 131 and / or the second layer 132.
[0480] As an example, the first layer 131 may be in direct contact with the hole transport layer included in the hole transport region 120. As another example, the first layer 131 may be in direct contact with the light-emitting auxiliary layer disposed on the hole transport layer.
[0481] As an example, the second layer 132 may be in direct contact with the buffer layer included in the electron transport region 140.
[0482] The first layer 131 may include the first compound. The first layer 131 may be composed of the first compound. For example, the first layer 131 may not include the second compound. The first layer 131 may also be referred to as a p-type photoactive layer or a donor layer.
[0483] The second layer 132 may include the second compound. The second layer 132 may be composed of the second compound. For example, the second layer 132 may not include the first compound. The second layer 132 may also be referred to as an n-type photoactive layer or an acceptor layer.
[0484] The third layer 133 may include the first compound and the second compound. For example, the first compound and the second compound may be mixed and included in the third layer 133. The third layer 133 may also be referred to as a mixing layer.
[0485] That is, the photoactive layer 135 may have a three-layer structure divided into a first layer 131 including the first compound, a third layer 133 including both the first compound and the second compound, and a second layer 132 including the second compound.
[0486] The photoactive layer 135 may absorb incident light to generate excitons. The excitons may generate holes and electrons. The holes generated by the photoactive layer 135 may move to the first electrode 110 through the hole transport region 120. The electrons generated by the photoactive layer 135 may move to the second electrode 150 through the electron transport region 140.
[0487] That is, the photoactive layer 135 can absorb light to generate an electrical signal. Specifically, the first compound included in each of the first layer 131 and the third layer 133 can act as a donor that supplies electrons, and the second compound included in each of the second layer 132 and the third layer 133 can act as an acceptor that accepts electrons. Therefore, the optoelectronic element 30 including the photoactive layer 135 can act as a photosensor. For example, the optoelectronic element 30 can act as a fingerprint recognition sensor, for which reference is made to Figure 5 described below.
[0488] [Electronic device]
[0489] The light-emitting element 10 and the optoelectronic elements 30, 31, and 32 can be included in various electronic devices. For example, the electronic device can be a display device, a light-emitting device, an authentication device, or the like.
[0490] The electronic device (e.g., a light-emitting device), in addition to the light-emitting element 10 and the optoelectronic elements 30, 31, and 32, may further include i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and / or the color conversion layer can be disposed in the traveling direction of at least one of the lights emitted from the light-emitting element 10. For example, the light emitted from the light-emitting element 10 can be blue light or white light. For the description of the light-emitting element 10, reference is made to the above content. According to an example, the color conversion layer can include quantum dots. The quantum dots can be, for example, the quantum dots described in this specification.
[0491] The electronic device can include a first substrate. It is possible that the first substrate includes a plurality of sub-pixel regions, the color filter includes a plurality of color filter regions corresponding to each of the plurality of sub-pixel regions, and the color conversion layer includes a plurality of color conversion regions corresponding to each of the plurality of sub-pixel regions.
[0492] A pixel defining film is disposed between the plurality of sub-pixel regions to define each sub-pixel region.
[0493] The color filter may further include a plurality of color filter regions and a light-shielding pattern disposed between the plurality of color filter regions, and the color conversion layer may further include a plurality of color conversion regions and a light-shielding pattern disposed between the plurality of color conversion regions.
[0494] The plurality of color filter regions (alternatively, a plurality of color conversion regions) may include a first region that emits a first color light; a second region that emits a second color light; and / or a third region that emits a third color light, where the first color light, the second color light, and / or the third color light have different maximum emission wavelengths from each other. For example, 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. For example, the plurality of color filter regions (alternatively, a plurality of color conversion regions) may include quantum dots. Specifically, 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. For the description of quantum dots, refer to the content described in this specification. The first region, the second region, and / or the third region may each further include a scatterer.
[0495] For example, the light-emitting element 10 may emit a first light, the first region may absorb the first light to emit a 1-1 color light, the second region may absorb the first light to emit a 2-1 color light, and the third region may absorb the first light to emit a 3-1 color light. At this time, the 1-1 color light, the 2-1 color light, and the 3-1 color light may have different maximum emission wavelengths from each other. Specifically, the first light may be blue light, the 1-1 color light may be red light, the 2-1 color light may be green light, and the 3-1 color light may be blue light.
[0496] In addition to the optoelectronic elements 30, 31, 32, and the light-emitting element 10 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, and any one of the source electrode and the drain electrode may be electrically connected to any one of the first electrode and the second electrode of the light-emitting element 10.
[0497] The thin-film transistor may further include a gate electrode, a gate insulating film, etc.
[0498] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, etc.
[0499] The electronic device may further include a sealing portion that seals the photoelectric elements 30, 31, 32 and the light-emitting element 10. The sealing portion may be disposed between the color filter and / or the color conversion layer and the light-emitting element 10. The sealing portion may block external gas and moisture from penetrating into the photoelectric elements 30, 31, 32 and the light-emitting element 10 while allowing the light from the light-emitting element 10 to exit to the outside. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin film encapsulation layer including one or more organic layers and / or inorganic layers. When the sealing portion is a thin film encapsulation layer, the electronic device may be flexible.
[0500] On the sealing portion, in addition to the color filter and / or the color conversion layer, various functional layers may be further disposed according to the use of the electronic device. Examples of the functional layers may include a touch screen layer, a polarizing layer, etc. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer. The authentication device may be, for example, a biometric authentication device that authenticates an individual using biometric information (such as a fingertip, a pupil, etc.).
[0501] The authentication device may further include a biometric information collection mechanism in addition to the photoelectric elements 30, 31, 32 and the light-emitting element 10 as described above.
[0502] The electronic device may be applied to various displays, light sources, illuminations, personal computers (such as mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, electronic game consoles, medical devices (such as electronic thermometers, sphygmomanometers, glucometers, pulse measurement devices, pulse wave measurement devices, electrocardiogram display devices, ultrasonic diagnostic devices, endoscope display devices), fish finders, various measuring devices, instruments (such as instruments for vehicles, airplanes, ships), projectors, sensors (such as automotive sensors, household sensors), solar cells, etc.
[0503] [Electronic device]
[0504] The photoelectric elements 30, 31, 32 may be included in various electronic devices.
[0505] For example, the electronic device including the optoelectronic elements 30, 31, 32 may be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, indoor or outdoor lighting and / or signal lights, a head-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a mobile phone, a tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a 3D display, a virtual reality or augmented reality display, a vehicle, a video wall including tiled together multiple displays, a theater or stadium screen, a light therapy device, a plaque, an automotive sensor, a household sensor, and a solar cell, among others.
[0506] The optoelectronic elements 30, 31, 32 have excellent optoelectronic characteristics and the like, so the electronic device including the optoelectronic elements 30, 31, 32 may have functions of an optical sensor such as a fingerprint recognition sensor.
[0507] [Regarding Figure 5 the description of 6]
[0508] Figure 5 is a cross-sectional view of an electronic device according to an example of the present invention.
[0509] Figure 5 The electronic device of includes a substrate 100, a thin film transistor TFT, a light emitting element 10, an optoelectronic element 30, and a packaging portion 300. Figure 5 The optoelectronic element 30 of may be the optoelectronic element 30 described with reference to Figure 1 but is not limited thereto. For example, Figure 5 the optoelectronic element 30 of may be Figure 3 the optoelectronic element 31 of or Figure 4 the optoelectronic element 32 of.
[0510] 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 may serve to prevent impurities from penetrating through the substrate 100 and provide a flat surface above the substrate 100.
[0511] The thin film transistor TFT may be disposed on the buffer layer 210. The thin film transistor TFT may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
[0512] The active layer 220 may include an inorganic semiconductor such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor, and includes a source region, a drain region, and a channel region.
[0513] Above the active layer 220, a gate insulating film 230 for insulating the active layer 220 and the gate electrode 240 may be disposed, and the gate electrode 240 may be disposed above the gate insulating film 230.
[0514] An interlayer insulating film 250 may be disposed above the gate electrode 240. The interlayer insulating film 250 functions to be disposed between the gate electrode 240 and the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to insulate them.
[0515] The source electrode 260 and the drain electrode 270 may be disposed 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 the drain region of the active layer 220, and the source electrode 260 and the drain electrode 270 may be disposed to be in contact with the exposed source region and drain region of the active layer 220.
[0516] The light-emitting element 10 and the optoelectronic element 30 may be disposed on the thin-film transistor TFT.
[0517] The thin-film transistor TFT electrically connected to the light-emitting element 10 may transmit an electrical signal for driving the light-emitting element 10. The thin-film transistor TFT electrically connected to the optoelectronic element 30 may transmit an electrical signal generated by the optoelectronic element 30. The thin-film transistor TFT is covered and protected with a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or a combination thereof. The light-emitting element 10 and the optoelectronic element 30 are disposed on the passivation layer 280.
[0518] The light-emitting element includes a first electrode 110, a hole transport region 120, a light-emitting layer 130, an electron transport region 140, and a second electrode 150. The optoelectronic element 30 includes a first electrode 110, a hole transport region 120, a photoactive layer 135, an electron transport region 140, and a second electrode 150. The first electrode 110 may be disposed on the passivation layer 280. The passivation layer 280 may be configured to expose a predetermined region without covering the entire source electrode 260 and drain electrode 270, and the first electrode 110 may be disposed to be connected to the exposed source electrode 260 and drain electrode 270.
[0519] On the first electrode 110, a pixel defining film 290 including an insulator may be disposed. The pixel defining film 290 may expose a predetermined region of the first electrode 110. The pixel defining film 290 may be an organic film such as polyimide or polyacrylic acid series.
[0520] The hole transport region 120 can be disposed on the pixel defining film 290. The hole transport region 120 included in the light-emitting element 10 and the hole transport region 120 included in the photoelectric element 30 can be integrally formed. The hole transport region 120 included in the light-emitting element 10 and the hole transport region 120 included in the photoelectric element 30 can be disposed on the pixel defining film 290, connected to each other and include substantially the same material, and can be substantially simultaneously formed.
[0521] Each of the light-emitting layer 130 and the photoactive layer 135 can be disposed on the hole transport region 120. Each of the light-emitting layer 130 and the photoactive layer 135 can overlap with the predetermined region of the first electrode 110 exposed through the pixel defining film 290.
[0522] The electron transport region 140 can be disposed on the light-emitting layer 130 and the photoactive layer 135. The electron transport region 140 included in the light-emitting element 10 and the electron transport region 140 included in the photoelectric element 30 can be integrally formed. The electron transport region 140 included in the light-emitting element 10 and the electron transport region 140 included in the photoelectric element 30 can be disposed on the pixel defining film 290, connected to each other and include substantially the same material, and can be substantially simultaneously formed.
[0523] The second electrode 150 can be disposed on the electron transport region 140. The second electrode 150 included in the light-emitting element 10 and the second electrode 150 included in the photoelectric element 30 can be integrally formed. The second electrode 150 included in the light-emitting element 10 and the second electrode 150 included in the photoelectric element 30 can be disposed on the pixel defining film 290, connected to each other and include substantially the same material, and can be substantially simultaneously formed.
[0524] A cover layer 170 can be further formed on the second electrode 150. The cover layer 170 can be formed to cover the second electrode 150.
[0525] An encapsulation part 300 can be disposed on the cover layer 170. The encapsulation part 300 can function to be disposed on the light-emitting element 10 and the photoelectric element 30 to protect the light-emitting element 10 and the photoelectric element 30 from the influence of moisture or oxygen. The encapsulation part 300 can include silicon nitride (SiN x ), silicon oxide (SiO x) An inorganic film of indium tin oxide, indium zinc oxide, or any combination thereof, an organic film containing polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resin (e.g., polymethyl methacrylate, polyacrylic acid, etc.), epoxy resin (e.g., AGE (aliphatic glycidyl ether)), or any combination thereof, or a combination of an inorganic film and an organic film.
[0526] The light-emitting element 10 can emit lights L1, L2, and L3. For example, the lights L1, L2, and L3 can be red light, green light, blue light, or near-infrared light.
[0527] A part of the emitted lights L1, L2, and L3, i.e., light l3, can be incident on an object 600 outside the electronic device. For example, the object 600 can be a finger of the user of the electronic device. The light L3' reflected from the object 600 can be incident on the photoelectric element 30.
[0528] The photoactive layer 135 can absorb the incident light L3' to form excitons. The excitons can generate holes and electrons. That is, the photoactive layer 135 can absorb light to generate an electrical signal. Specifically, the first compound included in the photoactive layer 135 can act as a donor that supplies electrons, and the second compound included in the photoactive layer 135 can act as an acceptor that accepts electrons. That is, the photoelectric element 30 can detect the energy of the light L3' and convert it into an electrical signal. Therefore, the photoelectric element 30 can identify the object 600 that contacts (or approaches) the electronic device. Therefore, the photoelectric element 30 including the photoactive layer 135 can act as a photosensor (e.g., a fingerprint recognition sensor).
[0529] Figure 6 is a cross-sectional view of an electronic device according to another example of the present invention.
[0530] Figure 6 The electronic device, except that a light-shielding pattern 500 and a functional region 400 are further disposed above the encapsulation portion 300, is the same as the Figure 5 electronic device. The functional region 400 can be i) a color filter region, ii) a color conversion region, or iii) a combination of a color filter region and a color conversion region. According to one example, Figure 6 the light-emitting element 10 included in the electronic device can be a series-connected light-emitting element.
[0531] [Regarding the Figure 7 description]
[0532] Figure 7FIG. 0 is a perspective view schematically showing an electronic device 1 including an optoelectronic element according to an example of the present invention. The electronic device 1 is a device for displaying moving images or still images, and can be not only a mobile phone, a smart phone, a tablet personal computer, a mobile communication terminal, an electronic notebook, an e-book, a PMP (portable multimedia player), a navigator, an UMPC (Ultra Mobile PC), or other portable electronic devices, but also various products such as a television, a portable computer, a monitor, a billboard, or an internet of things (IOT), or a part thereof. In addition, the electronic device 1 can be a wearable device such as a smart watch, a watch phone, a glasses-type display, or a head mounted display (HMD), or a part thereof. Obviously, the present invention is not limited thereto. For example, the electronic device 1 can be a CID (Center Information Display) configured in the dashboard of an automobile and the center fascia or instrument panel of the automobile, a room mirror display replacing the side view mirror of the automobile, an in-vehicle entertainment device for the rear seat of the automobile, or a display configured on the back of the front seat, a Head Up Display (HUD) provided in the front of the vehicle or projected onto the front window glass, or a Computer Generated Hologram Augmented Reality Head Up Display (CGH AR HUD). For ease of explanation, Figure 7 a case where the electronic device 1 is a smart phone is shown.
[0533] The electronic device 1 may include a display area DA and a non-display area NDA outside the display area DA. The display device can implement an image through an array of a plurality of pixels two-dimensionally arranged in the display area DA.
[0534] The non-display area NDA is an area where no image is displayed and can entirely surround the display area DA. In the non-display area NDA, a driver or the like for supplying an electric signal or power to a display element disposed in the display area DA can be arranged. In the non-display area NDA, a pad, which is an area capable of electrically connecting electronic components or a printed circuit board, etc., can be arranged.
[0535] The length in the x-axis direction and the length in the y-axis direction of the electronic device 1 may be different from each other. For example, as Figure 7 shown, the length in the x-axis direction may be shorter than the length in the y-axis direction. As yet another example, the length in the x-axis direction and the length in the y-axis direction may be the same. As yet another example, the length in the x-axis direction may be longer than the length in the y-axis direction.
[0536] [Regarding Figure 8 the descriptions of FIGS. 9a to 9c]
[0537] Figure 8 FIG. 12 is a diagram schematically showing the exterior of a vehicle 1000 which is an electronic device including an optoelectronic element according to an example of the present invention. Figures 9a to 9c FIG. 13 is a diagram schematically showing the interior of the vehicle 1000 according to various examples of the present invention.
[0538] Referring to Figure 8 , Figure 9a , Figure 9b and Figure 9c , the vehicle 1000 may mean various devices that move a transported body such as a human, an article, or an animal from a starting point to a destination. The vehicle 1000 may include vehicles traveling on roads or tracks, ships moving on the sea or a river, and airplanes flying in the sky by the action of air, etc.
[0539] The vehicle 1000 may travel on roads or tracks. The vehicle 1000 may move in a predetermined direction according to the rotation of at least one wheel. For example, the vehicle 1000 may include three-wheeled or four-wheeled automobiles, construction machinery, two-wheeled automobiles, prime mover devices, bicycles, and trains traveling on tracks.
[0540] The vehicle 1000 may include a body having interior and exterior parts and a chassis provided with mechanical devices required for traveling as the remaining parts other than the body. The exterior parts of the body may include a front panel, a hood, a roof panel, a rear panel, a trunk, and fillers provided at the boundaries between doors. The chassis of the vehicle 1000 may include a power generation device, a power transmission device, a traveling device, a steering device, a braking device, a suspension device, a transmission device, a fuel device, front, rear, left, and right wheels, etc.
[0541] The vehicle 1000 may include side window glasses 1100, a front window glass 1200, side mirrors 1300, a combination meter 1400, a center console 1500, a front passenger dashboard 1600, and a display device 2.
[0542] The side window glasses 1100 and the front window glass 1200 may be divided by fillers disposed between the side window glasses 1100 and the front window glass 1200.
[0543] The side window glass 1100 can be provided on the side of the vehicle 1000. In one embodiment, the side window glass 1100 can be provided on the door of the vehicle 1000. The side window glass 1100 can be provided in plurality and face each other. In one embodiment, the side window glass 1100 can include a first side window glass 1110 and a second side window glass 1120. In one embodiment, the first side window glass 1110 can be arranged adjacent to the combination meter 1400. The second side window glass 1120 can be arranged adjacent to the co-driver instrument panel 1600.
[0544] In one embodiment, the side window glasses 1100 can be spaced apart from each other in the x direction or the -x direction. For example, the first side window glass 1110 and the second side window glass 1120 can be spaced apart from each other in the x direction or the -x direction. In other words, the virtual straight line L connecting the side window glasses 1100 can extend in the x direction or the -x direction. For example, the virtual straight line L connecting the first side window glass 1110 and the second side window glass 1120 can extend in the x direction or the -x direction.
[0545] The front window glass 1200 can be provided in the front of the vehicle 1000. The front window glass 1200 can be arranged between the side window glasses 1100 facing each other.
[0546] The side mirror 1300 can provide a view of the rear of the vehicle 1000. The side mirror 1300 can be provided on the exterior part of the vehicle body. In one example, the side mirror 1300 can be provided in plurality. Any one of the plurality of side mirrors 1300 can be arranged outside the first side window glass 1110. Another one of the plurality of side mirrors 1300 can be arranged outside the second side window glass 1120.
[0547] The combination meter 1400 can be located in front of the steering wheel. The combination meter 1400 can be configured with a tachometer, a speedometer, a coolant temperature gauge, a fuel gauge, a turn indicator, a high beam indicator, a warning light, a seat belt warning light, an odometer, a driving recorder, an automatic shift lever indicator, a door open warning light, an engine oil warning light and / or a low fuel warning light.
[0548] The center console 1500 can include a control panel configured with a plurality of buttons for adjusting an audio device, an air conditioning device and a heater of a seat. The center console 1500 can be arranged on one side of the combination meter 1400.
[0549] The co-pilot instrument panel 1600 can be separated from the combination instrument 1400 by the center console 1500. In one embodiment, the combination instrument 1400 can be configured to correspond to the driver's seat (not shown), and the co-pilot instrument panel 1600 can be configured to correspond to the co-pilot seat (not shown). In one example, the combination instrument 1400 can be adjacent to the first side window glass 1110, and the co-pilot instrument panel 1600 can be adjacent to the second side window glass 1120.
[0550] In one embodiment, the display device 2 can include a display panel 3, and the display panel 3 can display images. The display device 2 can be configured inside the vehicle 1000. In one embodiment, the display device 2 can be configured between the side window glasses 1100 facing each other. The display device 2 can be configured on at least any one of the combination instrument 1400, the center console 1500, and the co-pilot instrument panel 1600.
[0551] The display device 2 can include an organic light emitting display device, an inorganic EL display device, a quantum dot display device, etc. Hereinafter, as an example of the display device 2 according to the present invention, an organic light emitting display device including a light emitting element according to the present invention will be described as an example, but the embodiments of the present invention can use display devices in various ways as described above.
[0552] Referring to Figure 9a , the display device 2 can be configured on the center console 1500. In one example, the display device 2 can display navigation information. In one example, the display device 2 can display information related to audio, video, or vehicle settings.
[0553] Referring to Figure 9b , the display device 2 can be configured on the combination instrument 1400. In this case, the combination instrument 1400 can represent operation information, etc. through the display device 2. That is, the combination instrument 1400 can be implemented digitally. The digitally implemented combination instrument 1400 can display vehicle information and driving information through images. For example, the pointer of the tachometer, the gauges, and various warning light icons can be displayed through digital signals.
[0554] Referring to Figure 9c, the display device 2 can be disposed on the co-driver's dashboard 1600. The display device 2 can be embedded in the co-driver's dashboard 1600 or located on the co-driver's dashboard 1600. In one example, the display device 2 disposed on the co-driver's dashboard 1600 can display images related to the information displayed in the combination meter 1400 and / or the information displayed in the center console 1500. In another example, the display device 2 disposed on the co-driver's dashboard 1600 can display information different from the information displayed in the combination meter 1400 and / or the information displayed in the center console 1500.
[0555] [Manufacturing Method]
[0556] Each layer included in the hole transport region 120, the light-emitting layer 130, the photoactive layer, and / or each layer included in the electron transport region 140 can be formed in a predetermined region by various methods such as vacuum evaporation, spin coating, casting, LB method (Langmuir-Blodgett), inkjet printing, laser printing, and laser thermal transfer (Laser Induced Thermal Imaging, LITI).
[0557] When forming each layer included in the hole transport region 120, the light-emitting layer 130, the photoactive layer, and / or each layer included in the electron transport region 140 by vacuum evaporation respectively, the evaporation conditions such as an evaporation temperature of about 100 to about 500 °C, a degree of vacuum of about 10 -8 to about 10 -3 Torr and an evaporation rate of about 0.01 to about can be selected in consideration of the materials included in the layer to be formed and the structure of the layer to be formed.
[0558] [Definition of Terms]
[0559] In this specification, a C3-C 60 carbocyclic group means a cyclic group having 3 to 60 carbon atoms in which only carbon atoms are ring-forming atoms. A C1-C 60 heterocyclic group means a cyclic group having 1 to 60 carbon atoms in which, in addition to carbon atoms, heteroatoms are also ring-forming atoms. The C3-C 60 carbocyclic group and the C1-C 60 heterocyclic group each can be a monocyclic group composed of one ring or a polycyclic group in which two or more rings are condensed with each other. For example, the number of ring-forming atoms of the C1-C 60 heterocyclic group can be 3 to 61.
[0560] In this specification, the cyclic group includes the C3-C 60 carbocyclic group and the C1-C60 All of the heterocyclic groups.
[0561] In this specification, the π electron-rich C3-C 60 cyclic group (πelectron-rich C3-C 60 Cyclic group) means a cyclic group having 3 to 60 carbon atoms that does not include *-N=*' as a ring-forming moiety.
[0562] In this specification, the π electron-deficient nitrogen-containing C1-C 60 cyclic group (πelectron-deficient nitrogen-containing C1-C 60 Cyclic group) means a heterocyclic group having 1 to 60 carbon atoms that includes *-N=*' as a ring-forming moiety.
[0563] For example,
[0564] the C3-C 60 carbocyclic group may be i) group T1 or ii) a condensed ring group in which two or more groups T1 are condensed with each other (for example, a cyclopentadiene group, an adamantyl group, a norbornyl group, a benzene group, a bicyclopentadiene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a perylene group, a pentaphene group, a heptalene group, a tetracene group, a picene group, a hexacene group, a pentacene group, a rubicene group, a coronene group, an ovalene group, an indene group, a fluorene group, a spirobifluorene group, a benzofluorene group, an indenophenanthrene group or an indenanthracene group),
[0565] the C1-C 60The heterocyclic group can be i) group T2, ii) a condensed ring group in which two or more groups T2 are condensed with each other, or iii) a condensed ring group in which one or more groups T2 and one or more groups T1 are condensed with each other (for example, pyrrole group, thiophene group, furan group, indole group, benzindole group, naphthindole group, isoindole group, benzisoindole group, naphthisoindole group, benzosilole group, benzothiophene group, benzofuran group, carbazole group, dibenzosilole group, dibenzothiophene group, dibenzofuran group, indeno[1,2,3-cd]carbazole group, indolo[3,2-b]carbazole group, benzofuro[2,3-b]carbazole group, benzothieno[2,3-b]carbazole group, benzosilolo[2,3-b]carbazole group, benzindolo[2,3-b]carbazole group, benzocarbazole group, benzonaphthofuran group, benzonaphthothiophene group, benzonaphthosilole group, benzofuro[2,3-b]dibenzofuran group, benzofuro[2,3-b]dibenzothiophene group, benzothieno[2,3-b]dibenzothiophene group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, oxadiazole group, thiazole group, isothiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzisoxazole group, benzothiazole group, benzisothiazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group, benzoisoquinoline group, quinoxaline group, benzoquinoxaline group, quinazoline group, benzoquinazoline group, phenanthroline group, cinnoline group, phthalazine group, naphthyridine group, imidazopyridine group, imidazopyrimidine group, imidazotriazine group, imidazopyrazine group, imidazopyridazine group, azacarbazole group, azafluorene group, azadibenzosilole group, azadibenzothiophene group, azadibenzofuran group, etc.),
[0566] The π - electron - rich C3 - C 60 The cyclic group can be i) group T1, ii) a condensed ring group in which two or more groups T1 are condensed with each other, iii) group T3, iv) a condensed ring group in which two or more groups T3 are condensed with each other, or v) a condensed ring group in which one or more groups T3 and one or more groups T1 are condensed with each other (for example, the C3 - C 60carbocyclic group, 1H-pyrrole group, silole group, borole group, 2H-pyrrole group, 3H-pyrrole group, thiophene group, furan group, indole group, benzoindole group, naphthoindole group, isoindole group, benzoisoindole group, naphthoisoindole group, benzosilole group, benzothiophene group, benzofuran group, carbazole group, dibenzosilole group, dibenzothiophene group, dibenzofuran group, indolocarbazole group, indolocarbazole group, benzofurancarbazole group, benzothiophenocarbazole group, benzosilolecarbazole group, benzindolocarbazole group, benzocarbazole group, benzonaphthofuran group, benzonaphthothiophene group, benzonaphthosilole group, benzofuran-dibenzofuran group, benzofuran-dibenzothiophene group, benzothiophene-dibenzothiophene group, etc.)
[0567] The π-deficient nitrogen-containing C1-C 60 The cyclic group can be i) group T4, ii) a condensed ring group formed by condensation of two or more groups T4 with each other, iii) a condensed ring group formed by condensation of one or more groups T4 and one or more groups T1 with each other, iv) a condensed ring group formed by condensation of one or more groups T4 and one or more groups T3 with each other, or v) a condensed ring group formed by condensation of one or more groups T4, one or more groups T1, and one or more groups T3 with each other (for example, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, oxadiazole group, thiazole group, isothiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzisoxazole group, benzothiazole group, benzisothiazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group, benzoisoquinoline group, quinoxaline group, benzoquinoxaline group, quinazoline group, benzoquinazoline group, phenanthroline group, cinnoline group, phthalazine group, naphthyridine group, imidazopyridine group, imidazopyrimidine group, imidazotriazine group, imidazopyrazine group, imidazopyridazine group, azacarbazole group, azafluorene group, azadibenzosilole group, azadibenzothiophene group, azadibenzofuran group, etc.).
[0568] The group T1 can be a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclobutene group, a cyclopentene group, a cyclopentadiene group, a cyclohexene group, a cyclohexadiene group, a cycloheptene group, an adamantane group, a norbornane (or bicyclo[2.2.1]heptane) group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octyl group or a benzene group.
[0569] The group T2 can be a furan group, a thiophene group, a 1H-pyrrole group, a silole group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an aza-silole group, an aza-borole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a tetrazine group, a pyrrolidine group, an imidazolidine group, a dihydropyrrole group, a piperidine group, a tetrahydropyridine group, a dihydropyridine group, a hexahydropyrimidine group, a tetrahydropyrimidine group, a dihydropyrimidine group, a piperazine group, a tetrahydropyrazine group, a dihydropyrazine group, a tetrahydropyridazine group or a dihydropyridazine group.
[0570] The group T3 can be a furan group, a thiophene group, a 1H-pyrrole group, a silole group or a borole group.
[0571] The group T4 can be a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an aza-silole group, an aza-borole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group or a tetrazine group.
[0572] In this specification, the so-called cyclic group, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, π-electron-rich C3-C 60 cyclic group or nitrogen-containing C1-C lacking π electrons 60The term "cyclic group" can be a group, monovalent group, or polyvalent group (e.g., divalent group, trivalent group, tetravalent group, etc.) that is condensed to any cyclic group according to the structure of the chemical formula in which the term is used.
[0573] For example, "phenyl group" can be a benzoyl group, phenyl group, phenylene group, etc., but it can be easily understood by those skilled in the art according to the structure of the chemical formula including the "phenyl group".
[0574] For example, examples of monovalent C3-C 60 carbocyclic groups and monovalent C1-C 60 heterocyclic groups can include C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C1-C 60 heteroaryl, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic heterocondensed polycyclic groups.
[0575] Examples of divalent C3-C 60 carbocyclic groups and divalent C1-C 60 heterocyclic groups can include C3-C 10 cycloalkylene, C1-C 10 heterocycloalkylene, C3-C 10 cycloalkenylene, C1-C 10 heterocycloalkenylene, C6-C 60 arylene, C1-C 60 heteroarylene, divalent non-aromatic condensed polycyclic groups, and divalent non-aromatic heterocondensed polycyclic groups.
[0576] In this specification, C1-C 60 alkyl means a straight-chain or branched-chain aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples thereof 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, isodecyl, sec-decyl, tert-decyl, etc.
[0577] In this specification, C1-C 60 alkylene means a divalent group having the same structure as the C1-C 60 alkyl.
[0578] In this specification, C2-C 60 alkenyl means a monovalent hydrocarbon group including one or more carbon-carbon double bonds in the middle or at the end of a C2-C 60 alkyl group. Specific examples thereof include vinyl, propenyl, butenyl, etc.
[0579] In this specification, C2-C 60 alkenylene means a divalent group having the same structure as the above-mentioned C2-C 60 alkenyl.
[0580] In this specification, C2-C 60 alkynyl means a monovalent hydrocarbon group including one or more carbon-carbon triple bonds in the middle or at the end of a C2-C 60 alkyl group. Specific examples thereof include ethynyl, propynyl, etc.
[0581] In this specification, C2-C 60 alkynylene means a divalent group having the same structure as the above-mentioned C2-C 60 alkynyl.
[0582] In this specification, C1-C 60 alkoxy means a monovalent group having the chemical formula -OA 101 (wherein A 101 is the above-mentioned C1-C 60 alkyl group). Specific examples thereof include methoxy, ethoxy, isopropoxy, etc.
[0583] In this specification, C3-C 10 cycloalkyl means a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantanyl, norbornanyl (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, etc.
[0584] In this specification, C3-C 10 cycloalkylene means a divalent group having the same structure as the above-mentioned C3-C 10 cycloalkyl.
[0585] In this specification, C1-C 10Heterocycloalkyl means a monovalent cyclic group having 1 to 10 carbon atoms and including at least one heteroatom as a ring-forming atom in addition to carbon atoms. Specific examples thereof include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl, tetrahydrobenzothienyl, etc.
[0586] In this specification, C1-C 10 Heterocycloalkylene means a divalent group having the same structure as the above-mentioned C1-C 10 heterocycloalkyl.
[0587] In this specification, C3-C 10 Cycloalkenyl is a monovalent cyclic group having 3 to 10 carbon atoms and means a group having at least one carbon-carbon double bond in the ring but not having aromaticity. Specific examples thereof include cyclopentenyl, cyclohexenyl, cycloheptenyl, etc.
[0588] In this specification, C3-C 10 Cycloalkenylene means a divalent group having the same structure as the above-mentioned C3-C 10 cycloalkenyl.
[0589] In this specification, C1-C 10 Heterocycloalkenyl is a monovalent cyclic group having 1 to 10 carbon atoms and including at least one heteroatom as a ring-forming atom in addition to carbon atoms, and having at least one double bond in the ring. The above-mentioned C1-C 10 Specific examples of the heterocycloalkenyl include 4,5-dihydro-1,2,3,4-oxadiazolyl, 2,3-dihydrofuranyl, 2,3-dihydrobenzothienyl, etc.
[0590] In this specification, C1-C 10 Heterocycloalkenylene means a divalent group having the same structure as the above-mentioned C1-C 10 heterocycloalkenyl.
[0591] In this specification, C6-C 60 Aryl means a monovalent group having a carbocyclic aromatic system with 6 to 60 carbon atoms.
[0592] C6-C 60 Arylene means a divalent group having a carbocyclic aromatic system with 6 to 60 carbon atoms.
[0593] The above-mentioned C6-C 60 Specific examples of the aryl include phenyl, indacenyl, naphthyl, azulyl, indacenyl, acenaphthylenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, Groups such as a base, a perylene base, a pentaphenyl group, a heptacenyl group, a tetracenyl group, a picene group, a hexaphenyl group, a pentaphenyl group, a rubicene group, a coronene group, and an ovalene group.
[0594] When the C6-C 60 Aryl and C6-C 60 When two or more rings are included in the arylene group, the two or more rings may be condensed with each other.
[0595] In this specification, C1-C 60 Heteroaryl means a monovalent group having a heteroaromatic system having 1 to 60 carbon atoms and including at least one heteroatom as a ring-forming atom in addition to carbon atoms.
[0596] C1-C 60 Heteroarylene means a divalent group having a heteroaromatic system having 1 to 60 carbon atoms and including at least one heteroatom as a ring-forming atom in addition to carbon atoms.
[0597] The C1-C 60 Specific examples of the heteroaryl group include a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a benzoisoquinolinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthrolinyl group, a phthalazinyl group, a naphthyridinyl group, etc.
[0598] When the C1-C 60 Heteroaryl and C1-C 60 When two or more rings are included in the heteroarylene group, the two or more rings may be condensed with each other.
[0599] In this specification, a monovalent non-aromatic condensed polycyclic group means a monovalent group in which two or more rings are condensed with each other, including only carbon as a ring-forming atom, and the whole molecule has non-aromaticity (for example, having 8 to 60 carbon atoms). Specific examples of the monovalent non-aromatic condensed polycyclic group include an indenyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, an indenophenanthryl group, an indenanthracenyl group, etc.
[0600] In this specification, a divalent non-aromatic condensed polycyclic group means a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.
[0601] In this specification, the monovalent non-aromatic condensed heteropolycyclic group means a monovalent group in which two or more rings are condensed with each other, including at least one heteroatom as a ring-forming atom in addition to carbon atoms, and the whole molecule has non-aromaticity (for example, having 1 to 60 carbon atoms). Specific examples of the monovalent non-aromatic condensed heteropolycyclic group include pyrrolyl, phenylthio, furyl, indolyl, benzindolyl, naphthylindolyl, isoindolyl, benzisoindolyl, naphthylisoindolyl, benzosilolyl, benzophenylthio, benzofuryl, carbazolyl, dibenzosilolyl, dibenzophenylthio, dibenzofuryl, azacarbazolyl, azafuryl, azadibenzosilolyl, azadibenzophenylthio, azadibenzofuryl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, imidazopyridyl, imidazopyrimidyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, indocarbazolyl, indolocarbazolyl, benzofurocarbazolyl, benzothienocarbazolyl, benzosilolocarbazolyl, benzindolocarbazolyl, benzocarbazolyl, benzonaphthofuryl, benzonaphthophenylthio, benzonaphthosilolyl, benzofurodibenzofuryl, benzofurodibenzophenylthio, benzothienodibenzophenylthio, etc.
[0602] In this specification, the divalent non-aromatic condensed heteropolycyclic group means a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
[0603] In this specification, C6-C 60 Aryloxy means -OA 102 (wherein A 102 is the C6-C 60 aryl).
[0604] The C6-C 60 Arylthio means -SA 103 (wherein A 103 is the C6-C 60 aryl).
[0605] In this specification, C7-C 60 Aralkyl means -A 104 A 105 (wherein A 104 is C1-C 54 alkylene, and A 105 is C6-C 59 aryl).
[0606] In this specification, C2-C 60 heteroaralkyl means -A 106 A 107 (wherein A 106 is C1-C 59 alkylene, and A 107 is C1-C 59 heteroaryl).
[0607] In this specification, "R 10a " can be
[0608] deuterium (-D), -F, -Cl, -Br, -I, hydroxy, cyano or nitro;
[0609] unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl, C2-C 60 heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 ), -N(Q 11 )(Q 12 ), -B(Q 11 )(Q 12 ), -C(=O)(Q 11 ), -S(=O)2(Q 11 ), -P(=O)(Q 11 )(Q 12 ) or any combination thereof-substituted C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 alkoxy;
[0610] unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl, C2-C60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 ), -N(Q 21 )(Q 22 ), -B(Q 21 )(Q 22 ), -C(=O)(Q 21 ), -S(=O)2(Q 21 ), -P(=O)(Q 21 )(Q 22 ) or a C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl or C2-C 60 heteroaralkyl; or
[0611] -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ).
[0612] In this specification, Q1 to Q3, Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 can each independently be hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxy; cyano; nitro; C1-C 60 alkyl; C2-C 60 alkenyl; C2-C 60 alkynyl; C1-C 60 alkoxy; or a C3-C 60 carbocyclic group, C1-C 60 heterocyclic group that is unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl or any combination thereof; C7-C 60 aralkyl; or C2-C60 Heteroarylkyl
[0613] In this specification, a heteroatom means any atom other than a carbon atom. Examples of the heteroatom include O, S, N, P, Si, B, Ge, Se, or any combination thereof.
[0614] In this specification, third-row transition metals include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), and gold (Au), etc.
[0615] In this specification, "Ph" means phenyl, "Me" means methyl, "Et" means ethyl, "tert-Bu" or "Bu t " means tert-butyl, and "OMe" means methoxy.
[0616] In this specification, "biphenyl" means "phenyl substituted by phenyl". The "biphenyl" belongs to "substituted phenyl" with a substituent of "C6-C 60 aryl".
[0617] In this specification, "terphenyl" means "phenyl substituted by biphenyl". The "terphenyl" belongs to "substituted phenyl" with a substituent of "C6-C 60 aryl substituted by C6-C 60 aryl".
[0618] In this specification, as long as there is no different definition, * and *' mean the bonding positions to adjacent atoms in the corresponding chemical formula or moiety.
[0619] In this specification, the x-axis, y-axis, and z-axis are not limited to the three axes on an orthogonal coordinate system and can be interpreted in a broad sense including this. For example, the x-axis, y-axis, and z-axis may be orthogonal to each other, but may also refer to different directions that are not orthogonal to each other.
[0620] Hereinafter, synthesis examples and examples are given to more specifically illustrate the compounds and light-emitting elements according to an example of the present invention. In the following synthesis examples, the molar equivalents of A and B in the expression "using B instead of A" are the same as each other.
[0621] [Examples]
[0622] Synthesis Example 1: Synthesis of Compound P2
[0623]
[0624] Synthesis of Intermediate P2-A
[0625] Dissolve 1.24 g (5 mmol) of 2,2':5',2”-terthiophene in 50 ml of dehydrated tetrahydrofuran. Dropwise add 4 ml (16.0 mmol) of 2.76 M n-BuLi hexane solution at -78 °C over 5 minutes, and stir at room temperature for 30 minutes. After cooling the temperature to -78 °C again, add 0.7 g (10 mmol) of dehydrated N,N'-dimethyl-d6-formamide and stir for 30 minutes, then raise the temperature to room temperature. Add water to terminate the reaction, extract three times with ethyl acetate, and add anhydrous magnesium sulfate to the extracted organic layer for drying. At this time, purify the obtained product by silica gel column chromatography (volume ratio of hexane:dichloromethane = 1:1) to obtain 0.98 g of compound P2-A (yield: 64%). Confirm the generated compound by MS / FAB.
[0626] C 14 H6D2O2S3: Calculated value 306.41, experimental value 306.56
[0627] Synthesis of Compound P2
[0628] After dissolving 1.07 g of intermediate P2-A (3.5 mmol) in 20 ml of ethanol, add 1.11 g (7.14 mmol) of 1,3-dimethyl-2-barbituric acid, stir at 50 °C for 2 hours, and then concentrate under reduced pressure. Recrystallize using chloroform and ethanol, dry the collected organic layer with magnesium sulfate, and purify the residue obtained by evaporating the solvent by silica gel column chromatography to obtain 1.29 g of compound P2 (yield 68%). Confirm the generated compound by 1 1H NMR (CDCl3, 400 mHz) and MS / FAB.
[0629] δ = 7.89 - 7.86 (s, 4H), 7.55 (s, 2H), 3.22 (s, 12H)
[0630] C 26 H 18 D2N4O6S3: Calculated value 582.66, experimental value 582.62
[0631] Synthesis Example 2: Synthesis of Compound P3
[0632]
[0633] Compound P3 was synthesized by the same method as the synthesis of Compound P2, except that 1,3-indanedione was used instead of 1,3-dimethyl-2-barbituric acid in the synthesis step of Compound P2 in Synthesis Example 1. The generated compound was confirmed by 1 1H NMR (CDCl3, 400 mHz) and MS / FAB.
[0634] δ = 7.89 - 7.86 (m, 4H), 7.73 - 7.71 (m, 8H), 7.55 (s, 2H)
[0635] C 32 H 14 D2O4S3: Calculated value 562.67, Experimental value 562.83
[0636] Synthesis Example 3: Synthesis of Compound P8
[0637]
[0638] Synthesis of Intermediate P8-A
[0639] 6.48 g (20.0 mmol) of 3,4'-dibromo-2,2'-bithiophene, 1.46 g (20.0 mmol) of 2-methylbutan-1-amine, 0.37 g (0.4 mmol) of Pd2(dba)3, 0.75 g (1.2 mmol) of BINAP and 5.76 g (60.0 mmol) of t-BuOK were dissolved in 90 ml of toluene and stirred at 120 °C for 24 hours. After cooling the reaction solution to room temperature, it was extracted three times with 50 ml of water and 50 ml of ether. The collected organic layer was dried with magnesium sulfate and the residue obtained by evaporating the solvent was purified by silica gel column chromatography to obtain 2.58 g of Intermediate P8-A (yield 55%). The generated compound was confirmed by MS / FAB.
[0640] C 12 H 13 NS2: Calculated value 235.36, Experimental value 235.41
[0641] Synthesis of Intermediate P8-B
[0642] Except that in the synthesis step of intermediate P2-A in Synthesis Example 1, intermediate P8-A was used instead of 2,2':5',2”-terthiophene and 2-bromothiophene was used instead of dehydrated N,N'-dimethyl-d6-formamide, intermediate P8-B was synthesized by the same method as the synthesis of the intermediate P2-A. The generated compound was confirmed by MS / FAB.
[0643] C 20 H 17 NS4: Calculated value 399.60, experimental value 399.69
[0644] Synthesis of Intermediate P8-C
[0645] Except that in the synthesis step of intermediate P2-A in Synthesis Example 1, intermediate P8-B was used instead of 2,2':5',2”-terthiophene, intermediate P8-C was synthesized by the same method as the synthesis of the intermediate P2-A. The generated compound was confirmed by MS / FAB.
[0646] C 22 H 15 D2NO2S4: Calculated value 457.64, experimental value 457.71
[0647] Synthesis of Compound P8
[0648] Except that in the synthesis step of compound P2 in Synthesis Example 1, P8-C was used instead of intermediate P2-A and malononitrile was used instead of 1,3-dimethyl-2-barbituric acid, compound P8 was synthesized by the same method as the synthesis of the compound P2. By 1 1H NMR (CDCl3, 400 mHz) and MS / FAB, the generated compound was confirmed.
[0649] δ = 7.51 - 7.49 (m, 2H), 7.21 - 7.17 (m, 4H), 4.05 - 4.03 (m, 2H), 2.05 - 2.02 (m, 1H), 0.91 (s, 6H)
[0650] C 28 H 15 D2N5S4: Calculated value 553.73, experimental value 553.83
[0651] Synthesis Example 4: Synthesis of Compound P9
[0652]
[0653] Compound P9 was synthesized using the same method as the synthesis of the compound P8, except that methylamine was used instead of 2-methylbutan-1-amine in the synthesis step of intermediate P8-A in Synthesis Example 3 and indanedione was used instead of malononitrile in the synthesis step of compound P8. By 1 1H NMR (CDCl3, 400 mHz) and MS / FAB were used to confirm the generated compound.
[0654] δ = 7.89 - 7.86 (m, 4H), 7.73 - 7.71 (m, 8H), 7.17 (s, 2H), 3.72 (s, 3H)
[0655] C 37 H 17 D2NO4S4: calculated value 671.81, experimental value 671.89
[0656] Synthesis Example 5: Synthesis of Compound P12
[0657]
[0658] Synthesis of Intermediate P12-A
[0659] 6.48 g (20.0 mmol) of 3,4'-dibromo-2,2'-bithiophene was dissolved in 150 ml of dehydrated tetrahydrofuran. 8 ml (32.0 mmol) of a 2.76 M n-butyllithium (n-BuLi) hexane solution was added dropwise at -78 °C for 5 minutes, and the mixture was stirred for 30 minutes. 2.71 g (21.0 mmol) of dichlorodimethylsilane was added at this temperature and stirred for 30 minutes, and the temperature was raised to room temperature. After stirring for 24 hours, water was added to terminate the reaction, and then the mixture was extracted three times with ethyl acetate, and anhydrous magnesium sulfate was added to the extracted organic layer for drying. At this time, the product obtained by silica gel column chromatography separation and purification (volume ratio of hexane:dichloromethane = 1:1) was used to obtain 3.34 g of compound P12-A (yield: 75%). The generated compound was confirmed by MS / FAB.
[0660] C 10 H 10 S2Si: calculated value 222.40, experimental value 222.48
[0661] Synthesis of Intermediate P12-B
[0662] Except for using intermediate P12-A to replace 2,2':5',2”-terthiophene and using 2-bromofuran to replace dehydrated N,N'-dimethyl-d6-formamide in the synthesis step of intermediate P2-A in Synthesis Example 1, intermediate P12-B was synthesized by the same method as the synthesis of the intermediate P2-A. The generated compound was confirmed by MS / FAB.
[0663] C 18 H 14 O2S2Si: calculated value 399.60, experimental value 399.69
[0664] Synthesis of Intermediate P12-C
[0665] Except for using intermediate P12-B to replace 2,2':5',2”-terthiophene in the synthesis step of intermediate P2-A in Synthesis Example 1, intermediate P12-C was synthesized by the same method as the synthesis of the intermediate P2-A. The generated compound was confirmed by MS / FAB.
[0666] C 22 H 16 D2O2S2Si: calculated value 408.60, experimental value 408.67
[0667] Synthesis of Compound P12
[0668] Except for using P12-C to replace intermediate P2-A and using 3-ethyl-2,5-thiazolidinedione to replace 1,3-dimethyl-2-barbituric acid in the synthesis step of compound P2 in Synthesis Example 1, compound P12 was synthesized by the same method as the synthesis of the compound P2. By 1 1H NMR (CDCl3, 400 mHz) and MS / FAB, the generated compound was confirmed.
[0669] δ = 7.44 - 7.42 (m, 2H), 7.24 - 7.22 (m, 2H), 7.14 (s, 2H), 3.72 - 3.70 (m, 4H), 1.28 - 1.25 (m, 6H), 0.14 (s, 6H)
[0670] C 30 H 22 D2N2O6S4Si: calculated value 666.87, experimental value 666.91
[0671] Synthesis Example 6: Synthesis of Compound P15
[0672]
[0673] Except for using 4,4-dimethyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene to replace intermediate P12-A and using 2-bromothiophene to replace 2-bromofuran in the synthesis step of intermediate P12-B in Synthesis Example 5, the same method as the synthesis of intermediate P12-B is used. Also, except for using indanedione to replace 3-ethyl-2,5-thiazolidinedione in the synthesis step of Compound 12, Compound P15 is synthesized using the same method as the synthesis of Compound P12. By 1 1H NMR (CDCl3, 400 mHz) and MS / FAB are used to confirm the generated compound.
[0674] δ = 7.89 - 7.86 (m, 4H), 7.72 - 7.70 (m, 8H), 7.16 (s, 2H), 1.69 (s, 6H)
[0675] C 39 H 20 D2O4S4: Calculated value 684.85, experimental value 684.90
[0676] Synthesis Example 7: Synthesis of Compound P17
[0677]
[0678] Except for using 2-bromofuran to replace 2-bromothiophene and using malononitrile to replace 3-ethyl-2,5-thiazolidinedione in the synthesis step of P15 in Synthesis Example 6, Compound P17 is synthesized using the same method as the synthesis of Compound P15. By 1 1H NMR (CDCl3, 400 mHz) and MS / FAB are used to confirm the generated compound.
[0679] δ = 7.09 - 7.07 (m, 4H), 6.54 - 6.52 (m, 2H), 1.69 (s, 6H)
[0680] C 27 H 12 D2N4O4S2: Calculated value 492.57, experimental value 492.63
[0681] Synthesis Example 8: Synthesis of Compound P20
[0682]
[0683] Except for using benzo[1,2-b:4,5-b']dithiophene instead of intermediate P12-A and using 2-bromothiophene instead of 2-bromofuran in the synthesis step of intermediate P12-B in Synthesis Example 5, the same method as the synthesis of intermediate P12-B was used. And, except for using 1,3-dimethyl-2-barbituric acid instead of 3-ethyl-2,5-thiazolidinedione in the synthesis step of compound 12, compound P20 was synthesized using the same method as the synthesis of compound P12. By 1 1H NMR (CDCl3, 400 mHz) and MS / FAB were used to confirm the generated compound.
[0684] δ = 7.89 - 7.82 (m, 6H), 7.50 - 7.48 (m, 2H), 3.23 (s, 12H)
[0685] C 32 H 20 D2N4O6S4: Calculated value 688.80, experimental value 688.94
[0686] Synthesis Example 9: Synthesis of Compound P21
[0687]
[0688] Except for using indanedione instead of 1,3-dimethyl-2-barbituric acid in the synthesis step of compound P20 in Synthesis Example 8, compound P21 was synthesized using the same method as the synthesis of compound P20. By 1 1H NMR (CDCl3, 400 mHz) and MS / FAB were used to confirm the generated compound.
[0689] δ = 7.90 - 7.82 (m, 6H), 7.72 - 7.68 (m, 8H), 7.50 - 7.49 (m, 2H)
[0690] C 38 H 16 D2O4S4: Calculated value 764.91, experimental value 946.96
[0691] Synthesis Example 10: Synthesis of Compound P25
[0692]
[0693] Compound P25 was synthesized by the same method as the synthesis of compound P20, except that 3-(dicyanomethylene) indan-1-one was used instead of 1,3-dimethyl-2-barbituric acid in the synthesis step of compound P20 in Synthesis Example 8. The resulting compound was confirmed by 1 1H NMR (CDCl3, 400 mHz) and MS / FAB.
[0694] δ = 7.89 - 7.82 (m, 6H), 7.72 - 7.70 (m, 2H), 7.50 - 7.48 (m, 2H), 7.36 - 7.32 (m, 6H)
[0695] C 44 H 16 D2N4O2S4: Calculated value 688.81, Experimental value 688.86
[0696] Synthesis Example 11: Synthesis of Compound P33
[0697]
[0698] Except that 2,2':5',2”-quaterthiophene was used instead of 2,2':5',2”-terthiophene in the synthesis step of intermediate P2-A in Synthesis Example 1, the same method as the synthesis of intermediate P2-A was used. Also, except that indanedione and malonitrile were used instead of 1,3-dimethyl-2-barbituric acid in the synthesis step of compound P2, compound P33 was synthesized by the same method as the synthesis of compound P2. The resulting compound was confirmed by 1 1H NMR (CDCl3, 400 mHz) and MS / FAB.
[0699] δ = 7.89 - 7.86 (m, 2H), 7.72 - 7.70 (m, 4H), 7.55 - 7.51 (m, 5H), 7.19 (d, 1H)
[0700] C 30 H 12 D2N2O2S4: Calculated value 564.71, Experimental value 564.72
[0701] Synthesis Example 12: Synthesis of Compound P36
[0702]
[0703] Except for using 4H-dithieno[3,2-b:2',3'-d]pyrrole to replace intermediate P12-A in the synthesis step of intermediate P12-B in Synthesis Example 5, the same method as the synthesis of intermediate P12-B is used. And, except for using malononitrile to replace 3-ethyl-2,5-thiazolidinedione in the synthesis step of compound 12, compound P36 is synthesized using the same method as the synthesis of compound P12. By 1 1H NMR (CDCl3, 400 mHz) and MS / FAB were used to confirm the generated compound.
[0704] δ = 11.12 (s, 1H), 7.51 - 7.49 (m, 2H), 7.19 - 7.17 (m, 4H)
[0705] C 24 H7D2N5S4: Calculated value 497.62, experimental value 497.73
[0706] Synthesis Example 13: Synthesis of Compound P41
[0707]
[0708] Except for using 1,3-bis(methyl-d3)pyrimidine-2,4,6(1H,3H,5H)-trione to replace 1,3-dimethyl-2-barbituric acid in the synthesis step of compound P2 in Synthesis Example 1, compound P41 is synthesized using the same method as the synthesis of compound P2. By 1 1H NMR (CDCl3, 400 mHz) and MS / FAB were used to confirm the generated compound.
[0709] δ = 7.89 - 7.86 (m, 4H), 7.55 - 7.53 (m, 2H)
[0710] C 26 H6D 14 N4O6S3: Calculated value 594.73, experimental value 594.79
[0711] Synthesis Example 14: Synthesis of Compound P44
[0712]
[0713] Except for using dithieno[3,2-b:2',3'-d]thiophene to replace intermediate P12-A in the synthesis step of intermediate P12-B in Synthesis Example 5, the same method as the synthesis of intermediate P12-B is used. And, except for using 3-(methyl-d3)thiazolidine-2,5-dione to replace 3-ethyl-2,5-thiazolidinedione in the synthesis step of Compound 12, Compound P44 is synthesized using the same method as the synthesis of Compound P12. By 1 1H NMR (CDCl3, 400 mHz) and MS / FAB were used to confirm the generated compound.
[0714] δ = 7.42 - 7.40 (m, 2H), 7.24 - 7.20 (m, 2H), 7.10 (s, 2H)
[0715] C 26 H6D8N2O6S5: Calculated value 618.75, Experimental value 618.90
[0716] Synthesis Example 15: Synthesis of Compound P46
[0717]
[0718] Except for using 4,4-bis(methyl-d3)-4H-cyclopenta[2,1-b:3,4-b]dithiophene to replace intermediate P12-A in the synthesis step of intermediate P12-B in Synthesis Example 5, the same method as the synthesis of intermediate P12-B is used. And, except for using malononitrile to replace 3-ethyl-2,5-thiazolidinedione in the synthesis step of Compound 12, Compound P46 is synthesized using the same method as the synthesis of Compound P12. By 1 1H NMR (CDCl3, 400 mHz) and MS / FAB were used to confirm the generated compound.
[0719] δ = 7.51 - 7.49 (m, 2H), 7.19 - 7.16 (m, 4H)
[0720] C 27 H6D8N4S4: Calculated value 530.73, Experimental value 530.76
[0721] Synthesis Example 16: Synthesis of Compound P53
[0722]
[0723] Compound P53 was synthesized using the same method as the synthesis of compound P20, except that 3,3-bis(methyl-d3)-2,3-dihydro-1H-inden-1-one was used instead of 1,3-dimethyl-2-barbituric acid in the synthesis step of compound P20 in Synthesis Example 8. The resulting compound was confirmed by 1 1H NMR (CDCl3, 400 mHz) and MS / FAB.
[0724] δ = 7.89 - 7.82 (m, 6H), 7.66 - 7.50 (m, 8H), 7.41 - 7.39 (m, 2H)
[0725] C 42 H 16 D 14 O2S4: Calculated value 709.03, experimental value 709.11
[0726] Example 1
[0727] As the anode, a Corning 15 Ω / cm 2 ITO glass substrate was cut into pieces of 50 mm x 50 mm x 0.7 mm. After ultrasonic cleaning with isopropyl alcohol and pure water for 5 minutes respectively, it was irradiated with ultraviolet light for 30 minutes and exposed to ozone for cleaning, and then the glass substrate was set in a vacuum evaporation apparatus.
[0728] First, 2-TNATA was vacuum-evaporated above the substrate to form a hole injection layer with a thickness of, and then, a hole transport material, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter, NPB), which is a hole transport compound, was vacuum-evaporated with a thickness of to form a hole transport layer.
[0729] Above the hole transport layer, a Red auxiliary layer was evaporated with a thickness of, and then an active layer was evaporated The active layer is composed of a light absorption layer and a photoelectric conversion layer. As a light absorption material, a p-type semiconductor compound (p-type), i.e., compound P2, was evaporated, and as a photoelectric conversion organic material, an n-type semiconductor compound (n-type), i.e., compound N5, was evaporated. Then, above the light-emitting layer 130, Alq3 was evaporated with a thickness of as an electron transport layer, and then, above this electron transport layer, a halogenated alkali metal, i.e., LiF, was evaporated with a thickness of as an electron injection layer, and with a thickness of to form an electron transport layer. After that, above this electron transport layer, a halogenated alkali metal, i.e., LiF, was evaporated with a thickness of as an electron injection layer, and with a thickness of to form an electron injection layer, and with a thickness of The LiF / Al electrode is formed by vacuum-evaporating Al with a thickness on the (negative electrode), thereby manufacturing an organic electroluminescent element.
[0730]
[0731] Examples 2 to 16 and Comparative Examples 1 to 4
[0732] When forming the photoactive layer, in addition to using the p-type compound and the n-type compound described in Table 2, an optoelectronic element is manufactured by the same method as in Example 1.
[0733] Evaluation Example 1: Evaluation of Compound Properties
[0734] The evaporation temperature (T p ) of the compound synthesized in the synthesis example is measured using a vacuum thermogravimetric analyzer (v-TGA, vacuum-Thermogravimetric analysis) under a reference internal pressure, and the results are shown in Table 1.
[0735] In order to pre-verify the stability of the material in large-scale production, the thermal stability of the material is evaluated and verified over a long period under high vacuum and high temperature conditions using a thermal stability evaluation device.
[0736] After measuring the evaporation temperature with a thermogravimetric analyzer, the material filled in the ampoule is placed in a thermal stability evaluation device, and the thermal stability is evaluated for 100 hours at the measured temperature. In order to confirm the degree of denaturation of the material, HPLC (High Performance Liquid Chromatography) measurements are performed before and after placing the material in the thermal stability evaluation device, and the change in HPLC purity is shown in Table 1. Here, HPLC is a device that separates organic compounds in a solution by components and measures the content.
[0737]
Table 1
[0738]
[0739]
[0740] It can be confirmed from Table 1 that, compared with Comparative Example Compounds A, B, and SubNC, the HPLC purity of the compound according to the present invention decreases less after 100 hours of thermal stability evaluation. Therefore, it can be confirmed that the compound according to the present invention has relatively high heat resistance.
[0741] Evaluation Example 2: Evaluation of Photoelectric Element Properties
[0742] To evaluate the characteristics of the optoelectronic elements fabricated in each of Examples 1 to 16 and Comparative Examples 1 to 4, the external quantum efficiency (EQE) and the dark current density (J dark ) were measured and shown in Table 1 below.
[0743] Light (550 nm to 650 nm) was irradiated onto the optoelectronic element using a xenon lamp device. The maximum absorption wavelength (λ max ) was measured when the light was irradiated, and the converted current was measured. The external quantum efficiency (EQE) was calculated using the irradiated light and the measured current.
[0744] A voltage (-3V) was applied to the positive electrode using an IVL-25CH device. The current flowing when the voltage was applied was measured using a current meter (Keithley, Tektronix, USA). The dark current density (J dark ) was calculated using the measured current.
[0745]
Table 2
[0746]
[0747]
[0748]
[0749]
[0750] It can be confirmed from Table 2 that the optoelectronic elements according to Examples 1 to 16 have a maximum absorption wavelength at a wavelength corresponding to green light or red light, and have a high external quantum efficiency (EQE) and a low dark current density (J dark ) compared to the optoelectronic elements according to Comparative Examples 1 to 4. Thus, it can be confirmed that the optoelectronic elements according to Examples 1 to 16 have high optoelectronic characteristics and low noise compared to the optoelectronic elements according to Comparative Examples 1 to 4.
Claims
1. An organic compound represented by the following Chemical Formula 1: <Chemical Formula 1> In the Chemical Formula 1, Ar3 is C1-C 60 heteroarylene or a divalent non-aromatic hetero-condensed polycyclic group, n3 is an integer from 1 to 3, L1 is a C3-C that is unsubstituted or substituted by at least one R1 60 carbocyclic group or a C1-C that is unsubstituted or substituted by at least one R1 60 heterocyclic group, L2 is a C3-C carbon ring group that is unsubstituted or substituted by at least one R2, or a C1-C 60 heterocyclic group that is unsubstituted or substituted by at least one R2, 60 and n1 and n2 are each independently an integer from 1 to 3, CY1 and CY2 are each independently a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group, X 11 and X 12 are each independently C(R 41 )(R 42 ), Si(R 41 )(R 42 ), N(R 41 ), P(R 41 ), O, S, C(R 41 ), Si(R 41 ), N, P, C(=O), C(=S) or C=C(R 43 )(R 44 ), X 11 and at least one of X 12 is C(=O), C(=S) or C=C(R 43 )(R 44 ), X 21 and X 22 each independently is C(R 51 )(R 52 ), Si(R 51 )(R 52 ), N(R 51 ), P(R 51 ), O, S, C(R 51 ), Si(R 51 ), N, P, C(=O), C(=S) or C=C(R 53 )(R 54 ), X 21 and at least one of X 22 is C(=O), C(=S) or C=C(R 53 )(R 54 ), a3, a4, and a5 are each independently an integer from 0 to 10, R1 to R5, R 41 、R 42 、R 51 and R 52 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted by at least one R 10a substituted C1-C 60 alkyl, unsubstituted or substituted by at least one R 10a substituted C2-C 60 alkenyl, unsubstituted or substituted by at least one R 10a substituted C2-C 60 alkynyl, unsubstituted or substituted by at least one R 10a substituted C1-C 60 alkoxy, unsubstituted or substituted by at least one R 10a substituted C3-C 60 carbocyclic group, unsubstituted or substituted by at least one R 10a substituted C1-C 60 heterocyclic group, unsubstituted or substituted by at least one R 10a substituted C6-C 60 aryloxy, unsubstituted or substituted by at least one R 10a substituted C6-C 60 arylthio, unsubstituted or substituted by at least one R 10a substituted C7-C 60 aralkyl, unsubstituted or substituted by at least one R 10a substituted C2-C 60 heteroaralkyl, -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), R 43 、R 44 、R 53 and R 54 are each independently an electron-withdrawing group, R 10a Yes deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, or nitro group; Unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl, C2-C 60 heteroaralkyl, -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, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 alkoxy; unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl, C2-C 60 heteroaralkyl, -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, a C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl or C2-C 60 heteroaralkyl; or -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), Q1 to Q3, Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 are each independently Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, or Unsubstituted or substituted by deuterium, -F, cyano, C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl or any combination thereof, a C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C7-C 60 aralkyl or C2-C 60 heteroaralkyl.
2. The organic compound according to claim 1, wherein the organic compound is represented by the following Chemical Formula 1-2: <Chemical Formula 1-2> In the Chemical Formula 1-2, Regarding Ar3, n3, CY1, CY2, X 11 , X 12 , X 21 , X 22 , the descriptions of a3, a4, a5 and R3 to R5 are respectively the same as those described in claim 1 Y1 and Y2 are each independently C(R6)(R7), Si(R6)(R7), N(R6), P(R6), O, or S, R6 and R7 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted by at least one R 10a substituted C1-C 60 alkyl, unsubstituted or substituted by at least one R 10a substituted C2-C 60 alkenyl, unsubstituted or substituted by at least one R 10a substituted C2-C 60 alkynyl, unsubstituted or substituted by at least one R 10a substituted C1-C 60 alkoxy, unsubstituted or substituted by at least one R 10a substituted C3-C 60 carbocyclic group, unsubstituted or substituted by at least one R 10a substituted C1-C 60 heterocyclic group, unsubstituted or substituted by at least one R 10a substituted C6-C 60 aryloxy, unsubstituted or substituted by at least one R 10a substituted C6-C 60 arylthio, unsubstituted or substituted by at least one R 10a substituted C7-C 60 aralkyl, unsubstituted or substituted by at least one R 10a substituted C2-C 60 heteroaralkyl, -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), Regarding R 11 and R 12 For the descriptions, refer to the description of R1 in claim 1 respectively. Regarding R 21 and R 22 For the descriptions, respectively refer to the description of R2 in claim 1.
3. The organic compound according to claim 1, wherein In Chemical Formula 1, the group represented by is a group selected from the following Chemical Formulas 1A to 1K: in the Chemical Formulas 1A to 1K, Ar 11 and Ar 12 each independently is a C3-C 30 carbocyclic group or a C1-C 30 heterocyclic group, X 13 、X 14 and X 15 Independently of each other, C(R 45 )(R 46 )、Si(R 45 )(R 46 )、N(R 45 )、P(R 45 )、O、S、C(R 45 )、Si(R 45 ), N, P, C(=O), C(=S) or C=C(R 43 )(R 44 ), For X 11 、X 12 、R4, a4, R 43 and R 44 The descriptions are the same as those described in claim 1 respectively. Regarding R 45 and R 46 For the descriptions, refer to the description of R4 in claim 1 respectively. * is a bonding site to an adjacent atom.
4. The organic compound according to claim 1, wherein The group represented by in Chemical Formula 1 is a group selected from the following Chemical Formulas 2A to 2K: in the Chemical Formulas 2A to 2K, Ar 21 and Ar 22 each independently is a C3-C 30 carbocyclic group or a C1-C 30 heterocyclic group, X 23 、X 24 and X 25 Independently of each other, C(R 55 )(R 56 )、Si(R 55 )(R 56 )、N(R 55 )、P(R 55 )、O、S、C(R 55 )、Si(R 55 ), N, P, C(=O), C(=S) or C=C(R 53 )(R 54 ), Regarding X 21 and X 22 R5, a5, R 53 and R 54 The descriptions are the same as those described in claim 1 respectively, Regarding R 55 and R 56 For the descriptions, please refer to the description of R5 in Claim 1 respectively. * is a bonding site to an adjacent atom.
5. The organic compound according to claim 1, wherein The group represented by in Chemical Formula 1 is a group selected from the following Chemical Formulas 3A to 3D: in the Chemical Formulas 3A to 3D, Ar 31 is a C3-C 30 carbocyclic group or a C1-C 30 heterocyclic group, Y 31 and Y 32 each independently is N(R 31 ), P(R 31 ), O or S, X 31 is C(R 31 )(R 32 ), Si(R 31 )(R 32 ), N(R 31 ), P(R 31 ), O or S, a3’ is an integer from 0 to 8, the description of R3 is the same as that described in claim 1, Regarding R 31 to R 34 For the descriptions, refer to the description of R3 in claim 1 respectively. *And* the' is the bonding position with the adjacent atom.
6. The organic compound according to claim 1, wherein the organic compound is any one of the following Compounds P1 to P55:
7. An optoelectronic element, wherein, Including: a first electrode; a second electrode facing the first electrode; a photoactive layer disposed between the first electrode and the second electrode; and a first compound, which is the organic compound according to any one of claims 1 to 6.
8. The optoelectronic element according to claim 7, wherein the optoelectronic element further includes: a second compound represented by any one of the following Chemical Formulas 2-1 to 2-6: In the Chemical Formulas 2-1 to 2-6, Y 41 and Y 42 each independently is C(Z 51 )(Z 52 ), Si(Z 51 )(Z 52 ), N(Z 51 ), P(Z 51 ), O, S, C(=O), C(=S) or C=C(Z 51 )(Z 52 ), Z 41 to Z 48 、Z 51 and Z 52 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted by at least one R 10a substituted C1-C 60 alkyl, unsubstituted or substituted by at least one R 10a substituted C2-C 60 alkenyl, unsubstituted or substituted by at least one R 10a substituted C2-C 60 alkynyl, unsubstituted or substituted by at least one R 10a substituted C1-C 60 alkoxy, unsubstituted or substituted by at least one R 10a substituted C3-C 60 carbocyclic group, unsubstituted or substituted by at least one R 10a substituted C1-C 60 heterocyclic group, unsubstituted or substituted by at least one R 10a substituted C6-C 60 aryloxy, unsubstituted or substituted by at least one R 10a substituted C6-C 60 arylthio, unsubstituted or substituted by at least one R 10a substituted C7-C 60 aralkyl, unsubstituted or substituted by at least one R 10a substituted C2-C 60 heteroaralkyl, -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), R 10a Yes deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, or nitro group; unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl, C2-C 60 heteroaralkyl, -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, the C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 alkoxy; Unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl, C2-C 60 heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof, substituted C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl or C2-C 60 heteroaralkyl; or -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), Q1 to Q3, Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 are each independently Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, or Unsubstituted or substituted by deuterium, -F, cyano, C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl or any combination thereof, a C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C7-C 60 aralkyl or C2-C 60 heteroaralkyl.
9. An electronic device, including: the optoelectronic element according to claim 7; and a light-emitting element that does not overlap with the optoelectronic element.
10. An electronic device, including: the optoelectronic element according to claim 7.