Near infrared light emitting diode and device including near infrared light emitting diode
By using osmium (Os)-containing organometallic compounds as the light-emitting layer in the near-infrared light-emitting diodes and optimizing the electrode material and layer structure, the problem of short service life of the near-infrared light-emitting diodes in the prior art is solved, and efficient emission of near-infrared light-emitting diodes is achieved Infrared light and long service life effect.
Patent Information
- Application Number
- CN201911298366.0
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2019-01-17
- Filing Date
- 2019-12-17
- Publication Date
- 2025-02-18
- Estimated Expiration
- 2039-12-17
AI Technical Summary
It is difficult to develop near-infrared light emitting diodes with long service life, especially while maintaining high-efficiency light emitting performance.
Using an osmium (Os)-containing organometallic compound as the near-infrared light emitting layer, the emission of near-infrared light is achieved by stacking an organic layer between the first electrode and the second electrode, and the specific electrode material and layer structure are optimized to extend. The service life of the diode.
It realizes efficient emission of near-infrared light, and significantly extends the service life of near-infrared light-emitting diodes, solving the problems of degraded luminous performance and short service life in the prior art.
Smart Images

Figure CN111446376B_ABST
Abstract
Description
[0001] CROSS-REFERENCE TO RELATED APPLICATIONS
[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2019-0006434, filed on January 17, 2019, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field
[0003] One or more embodiments relate to near-infrared light emitting diodes and devices including near-infrared light emitting diodes. Background Art
[0004] An organic light emitting device (OLED) is a self-emissive device having a wide viewing angle, a high contrast ratio, a short response time, and excellent characteristics in terms of brightness, driving voltage, and response speed compared to other devices.
[0005] An OLED may include a first electrode on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially stacked on the first electrode. Holes provided by the first electrode may move to the emission layer through the hole transport region. Electrons provided by the second electrode may move to the emission layer through the electron transport region. Carriers (e.g., holes and electrons) may recombine in the emission layer to generate excitons. These excitons transition (e.g., transition or relaxation) from an excited state to a ground state, thereby generating light. Summary of the invention
[0006] One or more embodiments include a near-infrared light emitting diode and a device including the near-infrared light emitting diode, which can emit near-infrared light and have a long service life.
[0007] Additional aspects of the embodiments will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the presented embodiments.
[0008] According to one or more embodiments, a near-infrared light emitting diode may include: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, wherein the organic layer may include a near-infrared light emitting layer, the near-infrared light emitting layer may include an organic metal compound containing osmium (Os), and the organic metal compound containing Os may be configured to emit near-infrared light having a maximum emission wavelength in a range of greater than 680 nanometers (nm) to less than 3,000 nm.
[0009] According to one or more embodiments, the device may include a near infrared light emitting diode. BRIEF DESCRIPTION OF THE DRAWINGS
[0010] These and / or other aspects of the embodiments will become apparent and more readily appreciated from the following description of the embodiments taken in conjunction with the accompanying drawings, in which:
[0011] Figure 1 is a schematic diagram of an embodiment of a near-infrared light emitting diode. DETAILED DESCRIPTION
[0012] Reference will now be made to the embodiment in more detail, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout the text. In this respect, the current embodiment may have different forms and should not be construed as being limited to the description set forth herein. Therefore, the embodiment is described below only by reference to the accompanying drawings to explain the aspects of the embodiment currently described. As used herein, the term "and / or" includes any combination and all combinations of one or more than one of the related listed items. A statement such as "at least one (kind)" modifies the elements of the entire column without modifying the single element of the column when it is before a column of elements.
[0013] The near-infrared light emitting diode may include a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode and including an emission layer, wherein the organic layer may include a near-infrared light emitting layer, and the near-infrared light emitting layer may include an organic metal compound containing Os.
[0014] The Os-containing organometallic compound may emit near-infrared light having a maximum emission wavelength in the range of 680 nanometers (nm) or more to 3,000 nm or less. For example, the Os-containing organometallic compound may emit near-infrared light having a maximum emission wavelength in the range of 680 nm to 3,000 nm, or any range subsumed therein (e.g., such as 680 nm to 850 nm).
[0015] In some embodiments, the Os-containing organometallic compound may emit near-infrared light having a maximum emission wavelength in a range of 690 nm or more and 850 nm or less (eg, a range of 690 nm to 850 nm).
[0016] In some embodiments, the Os-containing organometallic compound may emit near-infrared light having a maximum emission wavelength in the range of 700 nm to 850 nm (e.g., in the range of 700 nm to 850 nm). The Os-containing organometallic compound may be neutral. For example, the Os-containing organometallic compound may be an electrically neutral molecule.
[0017] In an embodiment, the Os-containing organometallic compound may be an organometallic compound represented by Formula 1:
[0018] Formula 1
[0019] M(L 1 ) n1 (L 2 ) n2
[0020] Wherein, in Formula 1, M may be Os.
[0021] In formula 1, L 1 The ligand represented by the formula 1-1 can be selected:
[0022] Formula 1-1
[0023]
[0024] Formula 1-1 can be understood by referring to the description provided herein below.
[0025] In formula 1, n1 represents the ligand L 1 and n1 can be an integer from 1 to 4. When n1 is 2 or greater than 2, at least two L 1 In some embodiments, n1 may be 2 or 3, but the embodiments are not limited thereto.
[0026] L in Formula 1 2 It can be an organic ligand. 2 This can be understood by referring to the description provided herein below.
[0027] In formula 1, n2 represents the ligand L 2 and n2 can be an integer from 0 to 4. When n2 is 2 or greater than 2, at least two L 2 In some embodiments, n2 may be 0, 1 or 2, but the embodiments are not limited thereto.
[0028] In Formula 1, i) is selected from n1 number of L 1 At least two of, ii) selected from n2 number of L 2 At least two of, or iii) selected from n1 number of L 1 At least one of and selected from n2 number of L 2 At least one of can be optionally connected via a single bond, a double bond, *=N-*', *-N=*', *=C[(L 3 ) a3 -(R 3 )]-*'、*-C[(L 3 ) a3 -(R 3 )]=*'、*-N[(L 3 ) a3 -(R 3)]-*'、*-B(R 3 )-*'、*-P(R 3 )-*'、*-C(R 3 )(R 4 )-*'、*-Si(R 3 )(R 4 )-*'、*-Ge(R 3 )(R 4 )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) 2 -*'、*-C(R 3 )=*'、*=C(R 3 )-*'、*-C(R 3 )=C(R 4 )-*', *-C(=S)-*' or *-C≡C-*' are combined to form a tridentate ligand, a tetradentate ligand, a pentadentate ligand or a hexadentate ligand (as shown in, for example, compounds 39 to 42 provided herein below), and * and *' can each represent a site of connection to an adjacent atom.
[0029] In Formula 1-1, Ring A 1 and Ring A 2 Can be independently C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic group.
[0030] In some embodiments, Ring A 1 and Ring A 2 may each independently be i) a first ring, ii) a second ring, iii) a fused ring in which at least two first rings may be fused (e.g., bound together), iv) a fused ring in which at least two second rings may be fused (e.g., bound together), or v) a fused ring in which at least one first ring and at least one second ring may be fused (e.g., bound together),
[0031] The first ring may be a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a thiorrole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzothiorrole group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azathiorrole group, a diazathiorrole group or a triazathiorrole group, and
[0032] The second ring may be an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a cycloheptane group, a cycloheptadiene group, a cycloheptatriene group, a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, an oxasiline group, a thiasiline group, a dihydroazasiline group, a dihydrodisiline group, a dihydrosiline group, a dioxazone group, an oxathiine group, an oxazine group, a pyran group, a dithiine group, a thiazine group, a thiopyran group, a cyclohexadiene group, a dihydropyridine group, or a dihydropyrazine group.
[0033] In an embodiment, the first ring may be a pyrrole group, a thiadiazole group, a pyrazole group, an imidazole group or a triazole group, and the second ring may be a cyclohexene group, a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group or a pyridazine group, but the embodiment is not limited thereto.
[0034] In one or more than one embodiment, Ring A 1 and Ring A 2 can be independently a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, group, aperylene group, an azaperylene group, a benzoperylene group, an azabenzoperylene group, a naphthoperylene group, an azanaphthoperylene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthylene group, a pyrrole group, a thiophene group, a furan group, an indole group, a benzindole group, a naphthoindole group, an isoindole group, a benzisoindole group, a naphthoisoindole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermanol group, a benzogermanol group, a benzothiophene ... benzogermole) group, benzothiophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzoborol group, dibenzophosphol group, fluorene group, dibenzosilole group, dibenzogermol group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, dibenzothiophene 5,5-dioxide group, azacarbazole group, azadibenzoborol group, azadibenzophosphol group, azafluorene group, azadibenzothiophene azodibenzothiophene group, azodibenzogermanol group, azodibenzothiophene group, azodibenzoselenophene group, azodibenzofuran group, azodibenzothiophene 5-oxide group, azo-9H-fluorene-9-one group, azodibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, benzoquinoline group, isoquinoline group, benzoisoquinoline group, quinoxaline group, benzoquinoxaline group, quinazoline group, benzoquinazoline group, phenanthroline group, pyrazole group, imidazole group, The invention can be substituted with an oxazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, a dioxazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, a phthalazine group, a phthalidine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azulene group or a naphthyridine group.
[0035] In one or more than one embodiment, Ring A 1 and Ring A 2Each of the phenyl groups may be independently a phenyl group, a naphthyl group, an indole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, a benzoquinoline group, an isoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a phthalazine group, a phthalidine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azulene group or a naphthyridine group, but the embodiment is not limited thereto.
[0036] In formula 1-1, Z 31 and Z 32 can be independently a covalent bond, a coordination bond, O, S, C(R 7 )(R 8 )、Si(R 7 )(R 8 )、N(R 7 )、P(R 7 )、C(R 7 )(R 8 )(R 9 )、Si(R 7 )(R 8 )(R 9 )、N(R 7 )(R 8 ) or P(R 7 )(R 8 ).
[0037] In an embodiment, Z 31 It can be a covalent bond, O, S, C(R 7 )(R 8 )、Si(R 7 )(R 8 ) or N(R 7 ), and Z 32 It may be a coordination bond, but the embodiment is not limited thereto.
[0038] In formula 1-1, X 1 and X 2 They may each independently be C or N.
[0039] In some embodiments, X 1 Can be C or N, and X 2 It may be N, but the embodiment is not limited thereto.
[0040] In Formula 1-1, Ring A 1 and T 1 and T 1 and Ring A 2 Each may be linked via a single bond or a double bond. 1 and T 1 and T 1 and Ring A 2 Each can be connected via a single key.
[0041] In formula 1-1, T 1 It can be a single bond, a double bond, *=N-*', *-N=*', *=C[(L 5 ) a5 -(R 5 )]-*'、*-C[(L 5 ) a5 -(R 5 )]=*'、*-N[(L 5 ) a5 -(R 5 )]-*'、*-B(R 5 )-*'、*-P(R 5 )-*'、*-C(R 5 )(R 6 )-*'、*-Si(R 5 )(R 6 )-*'、*-Ge(R 5 )(R 6 )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) 2 -*'、*-C(R 5 )=*'、*=C(R 5 )-*'、*-C(R 5 )=C(R 6 )-*', *-C(=S)-*' or *-C≡C-*', wherein * and *' may each represent a connection site with an adjacent atom.
[0042] In an embodiment, T 1 Can be a single key.
[0043] L 3 and L 5 can be independently a single bond, unsubstituted or substituted with at least one R 10 Substituted C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10 Substituted C 1 -C 30a3 and a5 may each independently be an integer of 1 to 5.
[0044] In some embodiments, L 3 and L 5 Can be independently:
[0045] a single key; or
[0046] Each is unsubstituted or selected from deuterium, C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthenyl group, a fluorenyl group, a spiro-difluorenyl group, a spiro-benzofluorene-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, a phenanthrenyl group, a anthracenyl group, a fluoranthenyl group, a triphenylene group, a pyrenyl group, a phenyl group, a peryl group, a pentaphenyl group, a pyrrolyl group, a thienyl group, a furyl group, a silyl group, an indolyl group, an isoindolyl group, a purinyl group, a benzofuranyl group, a benzothienyl group, a benzosilyl group, a dibenzofuranyl group, a dibenzothienyl group, a dibenzosilyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, -Si(Q 51 )(Q 52 )(Q 53 )、-N(Q 51 )(Q 52 ) and -B(Q 51 )(Q 52 ) is at least one substituted phenyl group, pentylene group, indene group, naphthyl group, azulene group, indacene group, acenaphthylene group, fluorene group, spiro-bifluorene group, spiro-benzofluorene-fluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, group, a perylene group, a pentaphenyl group, a pyrrole group, a thiophene group, a furan group, a silole group, an indole group, an isoindole group, a purine group, a benzofuran group, a benzothiophene group, a benzosilole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, a carbazole group, a benzocarbazole group or a dibenzocarbazole group;
[0047] a3 and a5 can each independently be 1, 2 or 3.
[0048] R 1 To R 10can be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a substituted or unsubstituted C 1 -C 60 Alkyl groups, substituted or unsubstituted C 2 -C 60 Alkenyl groups, substituted or unsubstituted C 2 -C 60 Alkynyl group, substituted or unsubstituted C 1 -C 60 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 Aryl group, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio group, substituted or unsubstituted C 1 -C 60 heteroaryl group, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O) 2 (Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ), where Q 1 To Q 3 Each can be understood by referring to the description thereof provided herein.
[0049] In some embodiments, R 1 To R 6 and R 10 Can be independently:
[0050] hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group or a hydrazone group;
[0051] Each is unsubstituted or selected from deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, tetrahydro-2H-pyranyl group, morpholinyl group, phenyl group, (C 1 -C 10 alkyl)phenyl group, di(C 1 -C 10 alkyl)phenyl group, biphenyl group, di(phenyl)phenyl group, terphenyl group, naphthyl group, pyridyl group, pyrimidyl group, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ) at least one substituted C 1 -C 10 Alkyl group, C 2 -C 10 Alkenyl group, C 2 -C 10 Alkynyl group or C 1 -C 10 Alkoxy groups;
[0052] Each is unsubstituted or selected from deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3, -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C 1 -C 10 Alkyl group, C 2 -C 10 Alkenyl group, C 2 -C 10 Alkynyl group, C 1 -C 10 an alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a tetrahydro-2H-pyranyl group, a morpholinyl group, a dioxanyl group, a phenyl group, (C 1 -C 10 alkyl)phenyl group, di(C 1 -C 10 alkyl)phenyl group, biphenyl group, di(phenyl)phenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a benzofuranyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophene ... a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidinyl group, a 2,3-dihydro-1H-indenyl group, a 1,2,3,4-tetrahydronaphthyl group, a 2,3-dihydrobenzodioxinyl group, a benzodioxanyl group, an -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32)、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ) is at least one substituted cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, tetrahydro-2H-pyranyl group, morpholinyl group, dioxanyl group, phenyl group, (C 1 -C 10 alkyl)phenyl group, di(C 1 -C 10 alkyl)phenyl group, biphenyl group, di(phenyl)phenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a pyrrolyl group, a thienyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuroyl group, a 1,2,3,4-tetrahydronaphthyl group, a 2,3-dihydrobenzodioxazolyl group, a 1,2,3,4-tetrahydronaphthyl group, a 2,3-dihydrobenzodioxinyl group, or a benzodioxanyl group; or
[0053] -O(Q 1 )、-S(Q 1 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q1 )(Q 2 ),
[0054] Among them, Q 1 To Q 3 and Q 31 To Q 33 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C 1 -C 10 Alkyl group, C 2 -C 10 Alkenyl group, C 2 -C 10 Alkynyl group, C 1 -C 10 an alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a tetrahydro-2H-pyranyl group, a morpholinyl group, a dioxanyl group, a phenyl group, (C 1 -C 10 alkyl)phenyl group, di(C 1 -C 10 alkyl)phenyl group, biphenyl group, di(phenyl)phenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a benzoyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzo[pi]nyl group, a benzo[pi]nyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzo[pi]nyl group, a benzo[pi]nyl group, a quinol ... A furanyl group, a benzothienyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothienyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a 2,3-dihydro-1H-indenyl group, a 1,2,3,4-tetrahydronaphthyl group, a 2,3-dihydrobenzodioxinyl group or a benzodioxanyl group.
[0055] In an embodiment, R 1 To R 6 and R 10 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -CH 3 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, or one of the groups represented by Formula 3-1(1) to Formula 3-1(29), Formula 3-2(1) to Formula 3-2(21), Formula 3-3(1) to Formula 3-3(19), Formula 3-4(1) to Formula 3-4(4), Formula 3-5(1) to Formula 3-5(107), Formula 3-6(1) to Formula 3-6(10), and Formula 3-7(1) to Formula 3-7(27), but the embodiment is not limited thereto:
[0056]
[0057]
[0058]
[0059]
[0060]
[0061] In Formulas 3-1(1) to 3-1(29), 3-2(1) to 3-2(21), 3-3(1) to 3-3(19), 3-4(1) to 3-4(4), 3-5(1) to 3-5(107), 3-6(1) to 3-6(10), and 3-7(1) to 3-7(27),
[0062] Z 1 To Z 10 can be independently deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C 1 -C 10 Alkyl group, C 2 -C 10 Alkenyl group, C 2 -C 10 Alkynyl group, C 1 -C 10 an alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a tetrahydro-2H-pyranyl group, a morpholinyl group, a dioxanyl group, a phenyl group, (C 1 -C 10 alkyl)phenyl group, di(C 1 -C 10 alkyl)phenyl group, biphenyl group, di(phenyl)phenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a benzofuranyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophene ... a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidinyl group, a 2,3-dihydro-1H-indenyl group, a 1,2,3,4-tetrahydronaphthyl group, a 2,3-dihydrobenzodioxinyl group, a benzodioxanyl group, an -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ),
[0063] Where Q 31 To Q 33 can be understood by reference to the description thereof provided herein, respectively, and
[0064] * indicates the connection site with the adjacent atom.
[0065] Selected from R 1 To R 10 Two adjacent groups in may optionally be combined to form an unsubstituted or substituted group. 10a Substituted C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups, for example, are each unsubstituted or substituted with at least one R 10aA substituted phenyl group, a naphthyl group, an indole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, a benzoquinoline group, an isoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a phthalazine group, a phthalidine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azulene group, or a naphthyridine group. Here, R 10a By referring to the R 10 description to understand.
[0066] b1 and b2 in Formula 1-1 can each represent R 1 and R 2 b1 and b2 can each independently be an integer from 0 to 10. When b1 is 2 or greater, at least two R 1 When b2 is 2 or greater than 2, at least two R 2 In the embodiment, b1 and b2 may each independently be an integer of 0 to 4, but the embodiment is not limited thereto.
[0067] In formula 1-1, * 1 and* 2 and M in Formula 1.
[0068] M in Formula 1 and Z in Formula 1-1 31 or X 1 The bond between M in Formula 1 and Z in Formula 1-1 32 or X 2 The bonds between can each independently be covalent bonds or coordinate bonds (eg, coordinate covalent bonds or coordinate bonds).
[0069] In some embodiments, M in Formula 1 and Z in Formula 1-1 31 or X 1 The bond between can be a covalent bond, and M in Formula 1 and Z in Formula 1-1 32 or X 2 The bond between may be a coordination bond, but the embodiment is not limited thereto.
[0070] In the embodiment, the The part represented by may be selected from the group represented by formula A1-1 to formula A1-56 (for example, it may be selected from the group represented by formula A1-1, formula A1-8, formula A1-31 to formula A1-33, formula A1-46 to formula A1-48, formula A1-52, formula A1-53 and formula A1-56):
[0071]
[0072]
[0073] Wherein in Formula A1-1 to Formula A1-56,
[0074] X 1 and R 1 can be understood by reference to the description thereof provided herein, respectively,
[0075] b12 can be an integer from 0 to 2,
[0076] b13 can be an integer from 0 to 3,
[0077] b14 can be an integer from 0 to 4,
[0078] b15 can be an integer from 0 to 5,
[0079] b16 can be an integer from 0 to 6.
[0080] b17 can be an integer from 0 to 7,
[0081] *' represents the Z in formula 1-1 31 The attachment site, and
[0082] * indicates the same as T in formula 1-1 1 connection site.
[0083] In one or more than one embodiment, the The moiety represented by may be selected from the group represented by formula A2-1 to formula A2-50 (for example, the group represented by formula A2-1, formula A2-2, formula A2-8, formula A2-9, formula A2-11, formula A2-17, formula A2-22, formula A2-41, formula A2-43 and formula A2-44 to formula A2-50):
[0084]
[0085]
[0086] Wherein in Formula A2-1 to Formula A2-50,
[0087] X 2 and R 2can be understood by reference to the description thereof provided herein, respectively,
[0088] X 21 Can be selected from O, S, N (R 21 )、C(R 21 )(R 22 ) and Si(R 21 )(R 22 ),
[0089] R 21 and R 22 Each can be referred to by referring to the R 2 To understand the description,
[0090] b22 can be an integer from 0 to 2,
[0091] b23 can be an integer from 0 to 3,
[0092] b24 can be an integer from 0 to 4,
[0093] b25 can be an integer from 0 to 5,
[0094] b26 can be an integer from 0 to 6,
[0095] b27 can be an integer from 0 to 7,
[0096] *' represents the Z in formula 1-1 32 The attachment site, and
[0097] * indicates the same as T in formula 1-1 1 connection site.
[0098] In one or more than one embodiment, L in Formula 1 1 The ligand may be selected from those represented by formula 1-1(1) (as shown in, for example, compound 12):
[0099] Formula 1-1(1)
[0100]
[0101] Among them, in formula 1-1(1),
[0102] Ring A 1 , Ring A 2 , Z 31 , Z 32 , X 1 , X 2 , R 1 , R 2 , b1, b2, R 10a ,* 1 and* 2can be understood by reference to the description thereof provided herein, respectively,
[0103] Ring A 10 By referring to the ring A provided herein 1 description to understand, and
[0104] b10 may be understood by referring to the description of b1 provided herein.
[0105] L in Formula 1 2 Any suitable organic ligand may be used. 2 It can be selected from monodentate ligands, bidentate ligands, tridentate ligands and tetradentate ligands.
[0106] In an embodiment, in Formula 1, L 2 can be selected from monodentate ligands, and L 2 Can be selected from I - Br - , Cl - , sulfide, nitrate, azide, hydroxide, cyanate, isocyanate, thiocyanate, water, acetonitrile, pyridine, ammonia, carbon monoxide, P(Ph) 3 、P(Ph) 2 CH 3 PPh(CH 3 ) 2 and P(CH 3 ) 3 , but the implementation scheme is not limited thereto.
[0107] In some embodiments, in Formula 1, L 2 can be selected from bidentate ligands, and L 2 The oxalate may be selected from oxalate, acetylacetonate, picolinic acid, 1,2-bis(diphenylphosphino)ethane, 1,1-bis(diphenylphosphino)methane, glycinate, and ethylenediamine, but the embodiment is not limited thereto.
[0108] In one or more than one embodiment, L in Formula 1 2 The ligand may be selected from the group consisting of the ligands represented by Formula 4-1 to Formula 4-5:
[0109]
[0110] Among them, in Formula 4-1 to Formula 4-5,
[0111] Y 1 Can be C, P or As,
[0112] Y 11 Can be O, N, N(Z 13 )、P(Z13 )(Z 14 ) or As(Z 13 )(Z 14 ),
[0113] Y 12 Can be O, N, N(Z 15 )、P(Z 15 )(Z 16 ) or As(Z 15 )(Z 16 ),
[0114] T 11 Can be single bond, double bond, *-C(Z 11 )(Z 12 )-*'、*-C(Z 11 )(Z 12 )-C(Z 13 )(Z 14 )-*'、*-C(Z 11 )=C(Z 12 )-*'、*=C(Z 11 )-*'、*-C(Z 11 )=*'、*=C(Z 11 )-C(Z 12 )=C(Z 13 )-*'、*-C(Z 11 )=C(Z 12 )-C(Z 13 )=*'or*-N(Z 11 )-*', where * and *' can each represent a site of attachment to an adjacent atom, and *-C(Z 11 )=C(Z 12 )-*' 11 and Z 12 may be optionally combined to form an unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups (eg, each unsubstituted or substituted with at least one R 10asubstituted phenyl group, naphthyl group, indole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, benzoquinoline group, isoquinoline group, benzoisoquinoline group, quinoxaline group, benzoquinoxaline group, quinazoline group, benzoquinazoline group, phenanthroline group, pyrazole group, imidazole group, triazole group, tetrazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzothiazole group, benzooxadiazole group, benzothiadiazole group, phthalazine group, phthalazine group, imidazopyridine group, imidazopyrimidine group, imidazotriazine group, imidazopyrazine group, imidazopyridazine group, azulene group or naphthyridine group), wherein R 10a This can be understood by reference to the description thereof provided herein.
[0115] Y 13 To Y 16 can be independently C or N,
[0116] Y 17 Can be C, N (Z 17 ) or P(Z 17 ),
[0117] Ring A 11 and Ring A 12 Can be independently C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic groups,
[0118] Z 11 To Z 17 Each can be referred to by referring to the R 1 Describe to understand.
[0119] c11 and c12 may each independently be an integer from 0 to 10, and
[0120] * and *' may each independently represent a connection site with M in Formula 1.
[0121] In some embodiments, Ring A 11 and Ring A 12 Each can be referred to herein for ring A 1 description to understand.
[0122] In some embodiments, L in Formula 1 2 The ligand may be selected from the ligands represented by Formula 4-1 to Formula 4-3, wherein in Formula 4-1 to Formula 4-3, Y 1 Can be P, Y 11 It can be P(Z13 )(Z 14 ), and Y 12 It can be P(Z 15 )(Z 16 ).
[0123] In an embodiment, in Formula 1, n1 may be 2, n2 may be 1, and L 2 The ligand may be selected from the ligands represented by Formula 4-2 and Formula 4-3, wherein in Formula 4-2 and Formula 4-3, Y 11 It can be P(Z 13 )(Z 14 ), and Y 12 It can be P(Z 15 )(Z 16 ) (as shown in, for example, compound 1).
[0124] In one or more than one embodiment, in Formula 1, n1 may be 3, n2 may be 0, and is selected from three L 1 The two L 1 may be different from each other (as shown in, for example, compound 3).
[0125] In one or more than one embodiments, in Formula 1, n1 may be 3, n2 may be 0, and the three L 1 may be identical to each other (as shown, for example, in compound 4).
[0126] In one or more than one embodiments, in Formula 1, n1 may be 2, n2 may be 2, and L 2 The ligand may be selected from the ligand represented by formula 4-1, wherein Y in formula 4-1 1 It may be P (as shown in, for example, compound 22).
[0127] In one or more than one embodiments, in Formula 1, n1 may be 2, n2 may be 2, and L 2 The ligand may be selected from the ligand represented by formula 4-1, wherein in formula 4-1, Y 1 It can be P, and two L 1 and two L 2 Can be through a single bond, *-N[(L 3 ) a3 -(R 3 )]-*'、*-B(R 3 )-*'、*-P(R 3 )-*'、*-C(R 3 )(R 4 )-*'、*-Si(R 3 )(R 4)-*', *-S-*' or *-O-*' to form a hexadentate ligand (as shown in, for example, compound 39).
[0128] In one or more than one embodiment, the organometallic compound containing Os may be selected from Compound 1 to Compound 42, but the embodiment is not limited thereto:
[0129]
[0130]
[0131]
[0132]
[0133] Since the Os-containing organometallic compound represented by Formula 1 contains osmium and is configured to emit near-infrared light, an emitting diode using the Os-containing organometallic compound may emit near-infrared light while having a long lifetime.
[0134] Description of the drawings
[0135] Figure 1 A schematic diagram illustrating an embodiment of a near-infrared light emitting diode 10 is shown. The near-infrared light emitting diode 10 may include a first electrode 110 , an organic layer 150 , and a second electrode 190 .
[0136] In the following, we will combine Figure 1 The structure of the near-infrared light emitting diode 10 according to the embodiment and a method of manufacturing the near-infrared light emitting diode 10 according to the embodiment are described.
[0137] First electrode 110
[0138] exist Figure 1 In the embodiment, the substrate may be additionally located below the first electrode 110 or above the second electrode 190. The substrate may be a glass substrate or a plastic substrate each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.
[0139] The first electrode 110 may be formed by depositing or sputtering, on a substrate, a material for forming the first electrode 110. When the first electrode 110 is an anode, the material for forming the first electrode 110 may be selected from materials having a high work function that facilitate hole injection.
[0140] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2), zinc oxide (ZnO), and any combination thereof, but the embodiment is not limited thereto. In some embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, at least one of magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof may be used as a material for forming the first electrode 110, but the embodiment is not limited thereto.
[0141] The first electrode 110 may have a single-layer structure, or a multi-layer structure including two or more layers. In some embodiments, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO, but the embodiment is not limited thereto.
[0142] Organic layer 150
[0143] The organic layer 150 may be on the first electrode 110. The organic layer 150 may include a near-infrared light emitting layer including the above-described Os-containing organic metal compound.
[0144] The near-infrared emitting layer may further comprise a host described herein.
[0145] The organic layer 150 may include a hole transport region between the first electrode 110 and the near infrared light emitting layer and an electron transport region between the near infrared light emitting layer and the second electrode 190 .
[0146] Hole transport region in the organic layer 150
[0147] The hole transport region may have i) a single-layer structure composed of a single layer composed of a single material, ii) a single-layer structure composed of a single layer containing a plurality of different materials, or iii) a multi-layer structure having a plurality of layers containing a plurality of different materials.
[0148] The hole transport region may include at least one selected from the group consisting of a hole injection layer, a hole transport layer, an emission assisting layer, and an electron blocking layer.
[0149] For example, the hole transport region may have a single-layer structure or a multi-layer structure including a single layer containing a plurality of different materials, for example, a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission assisting layer structure, a hole injection layer / emission assisting layer structure, a hole transport layer / emission assisting layer structure, or a hole injection layer / hole transport layer / emission assisting layer structure, wherein the layers of each structure are sequentially stacked on the first electrode 110 in a prescribed order, but the embodiment is not limited thereto.
[0150] The hole transport region may include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), (polyaniline) / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by Formula 201, and a compound represented by Formula 202:
[0151]
[0152]
[0153] Formula 201
[0154]
[0155] Formula 202
[0156]
[0157] Among them, in equation 201 and equation 202,
[0158] L 201 To L 204 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene group, substituted or unsubstituted C 3 -C 10 Cycloalkenylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 Arylene group, substituted or unsubstituted C 1 -C 60 a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0159] L 205 Can be selected from *-O-*', *-S-*', *-N(Q 201 )-*', substituted or unsubstituted C 1 -C 20 Alkylene group, substituted or unsubstituted C2 -C 20 Alkenylene group, substituted or unsubstituted C 3 -C 10 Cycloalkylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene group, substituted or unsubstituted C 3 -C 10 Cycloalkenylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 Arylene group, substituted or unsubstituted C 1 -C 60 a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0160] xa1 to xa4 can each independently be an integer from 0 to 3,
[0161] xa5 can be an integer from 1 to 10, and
[0162] R 201 To R 204 and Q 201 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 Aryl group, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio group, substituted or unsubstituted C 1 -C 60 a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
[0163] In some embodiments, in Formula 202, R 201 and R 202 may optionally be bound via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group, and R 203and R 204 Bonding may optionally be via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group.
[0164] In one embodiment, in Formula 201 and Formula 202,
[0165] L 201 To L 205 can be independently selected from
[0166] a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthenylene group, a fluorenylene group, a spiro-difluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a phenylene group, a phenanthrenylene group, a fluoranthenylene group, a phenylene group, a pyrenyl ... a phenylene group, a tetraphenylene group, a perylene group, a perylene group, a pentphenylene group, a hexaphenylene group, a pentphenylene group, a rubinylene group, a coronene group, an ovphenylene group, a thienylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothienylene group, a dibenzofuranylene group, a dibenzothienylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilylene group, and a pyridylene group; and
[0167] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C 1 -C 10 a phenyl group substituted with an alkyl group, a phenyl group substituted with -F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenaltenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a tetraphenyl group, a pyrenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a rubinyl group, a coronet group, an ovaphenyl group, a thienyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilyl group, a pyridyl group, -Si(Q 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32 ) is at least one substituted phenylene group, pentalenylene group, indenylene group, naphthylene group, azulenylene group, heptalenylene group, indacenylene group, acenaphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, phenanthrenylene group, py ... a phenylene group, a tetraphenylene group, a perylene group, a perylene group, a pentphenylene group, a hexaphenylene group, a pentphenylene group, a rubidinyl group, a coronetyl group, an ovphenylene group, a thienylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothienylene group, a dibenzofuranylene group, a dibenzothienylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilylene group, and a pyridylene group,
[0168] Where Q 31 To Q 33 Can be independently selected from C 1 -C 10 Alkyl group, C 1 -C 10 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.
[0169] In one or more than one embodiments, xa1 to xa4 can each independently be 0, 1 or 2.
[0170] In one or more than one embodiments, xa5 can be 1, 2, 3 or 4.
[0171] In one or more than one embodiment, R 201 To R 204 and Q 201The phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthenyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenaltenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilyl group, and a pyridyl group; and
[0172] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C 1 -C 10 a phenyl group substituted with an alkyl group, a phenyl group substituted with -F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenaltenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a tetraphenyl group, a pyrenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a rubinyl group, a coronet group, an ovaphenyl group, a thienyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilyl group, a pyridyl group, -Si(Q 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32) is at least one substituted phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthenyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenaltenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilyl group, and a pyridyl group,
[0173] Where Q 31 To Q 33 Each can be understood by referring to the description thereof provided herein.
[0174] In one or more than one embodiment, in Formula 201, R 201 To R 203 At least one of may be selected from
[0175] fluorenyl groups, spiro-bifluorenyl groups, carbazolyl groups, dibenzofuranyl groups and dibenzothienyl groups; and
[0176] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C 1 -C 10 A phenyl group substituted with an alkyl group, a phenyl group substituted with -F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group substituted with at least one of the following, but the embodiment is not limited thereto.
[0177] In one or more than one embodiment, in Formula 202, i) R 201 and R 202 can be bound via a single bond, and / or ii) R 203 and R204 Can bind via a single bond.
[0178] In one or more than one embodiments, in Formula 202, R 201 To R 204 At least one of may be selected from
[0179] a carbazolyl group; and
[0180] is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C 1 -C 10 A carbazolyl group substituted with at least one of an alkyl group-substituted phenyl group, a -F-substituted phenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothienyl group, but the embodiment is not limited thereto.
[0181] The compound represented by Formula 201 can be represented by Formula 201A:
[0182] Formula 201A
[0183]
[0184] In some embodiments, the compound represented by Formula 201 may be represented by Formula 201A(1), but the embodiments are not limited thereto:
[0185] Formula 201A(1)
[0186]
[0187] In some embodiments, the compound represented by Formula 201 may be represented by Formula 201A-1, but the embodiments are not limited thereto:
[0188] Formula 201A-1
[0189]
[0190] In some embodiments, the compound represented by Formula 202 can be represented by Formula 202A:
[0191] Formula 202A
[0192]
[0193] In some embodiments, the compound represented by Formula 202 can be represented by Formula 202A-1:
[0194] Formula 202A-1
[0195]
[0196] In Formula 201A, Formula 201A(1), Formula 201A-1, Formula 202A, and Formula 202A-1,
[0197] L 201 To L 203 , xa1 to xa3, xa5 and R 202 To R 204 can be understood by reference to the description thereof provided herein, respectively,
[0198] R 211 and R 212 Each can be referred to by referring to the R 203 description to understand, and
[0199] R 213 To R 217 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C 1 -C 10 a phenyl group substituted with an alkyl group, a phenyl group substituted with -F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenaltenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, The invention also includes but is not limited to: a benzothiophenyl group, a tetraphenyl group, a peryl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a rubinyl group, a coronet group, an ovaphenyl group, a thienyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilyl group, and a pyridyl group.
[0200] The thickness of the hole transport region may be about to about In some embodiments, the range is about to about When the hole transport region includes at least one selected from a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be about to about In some embodiments, the range is about to about and the thickness of the hole transport layer may be about to about In some embodiments, the range is about to about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within any of these ranges, excellent hole transport characteristics may be obtained without a significant increase in driving voltage.
[0201] The emission auxiliary layer can improve the light emission efficiency by compensating the optical resonance distance according to the wavelength of the light emitted by the near-infrared light-emitting layer. The electron blocking layer can reduce or eliminate the flow of electrons from the electron transport region. The emission auxiliary layer and the electron blocking layer can include the aforementioned materials.
[0202] p-dopant
[0203] The hole transport region may contain a charge generating material along with the aforementioned materials to improve the conductive properties of the hole transport region. The charge generating material may be substantially uniformly or non-uniformly dispersed in the hole transport region.
[0204] The charge generating material may include, for example, a p-dopant.
[0205] In some embodiments, the lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant can be -3.5 eV or less.
[0206] The p-dopant may include at least one selected from the group consisting of a quinone derivative, a metal oxide, and a cyano group-containing compound, but the embodiment is not limited thereto.
[0207] In some embodiments, the p-dopant may include at least one selected from the following:
[0208] Quinone derivatives, for example tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);
[0209] Metal oxides, such as tungsten oxide or molybdenum oxide;
[0210] 1,4,5,8,9,12-Hexaazatriphenylene-hexacarbonitrile (HAT-CN); and
[0211] A compound represented by Formula 221, but the embodiment is not limited thereto:
[0212]
[0213] Formula 221
[0214]
[0215] Among them, in formula 221,
[0216] R 221 To R 223 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 Aryl group, substituted or unsubstituted C 1 -C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups and substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic groups, wherein R is selected from 221 To R 223 At least one of the following may include a cyano group, -F, -Cl, -Br, -I, C substituted with -F 1 -C 20 Alkyl groups, C substituted by -Cl 1 -C 20 Alkyl groups, C substituted with -Br 1 -C 20 Alkyl groups and C substituted by -I 1 -C 20 At least one substituent in the alkyl group.
[0217] Near infrared light emitting layer in the organic layer 150
[0218] The near-infrared light-emitting layer may include the Os-containing organometallic compound described herein.
[0219] In some embodiments, the near-infrared light-emitting layer may include a host and a dopant, and the dopant may include an organic metal compound containing Os. The amount of the dopant in the near-infrared light-emitting layer may generally range from about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but the embodiment is not limited thereto.
[0220] The thickness of the near-infrared emitting layer can be about to about In some embodiments, the range is about to about When the thickness of the near-infrared light-emitting layer is within any of these ranges, improved light-emitting characteristics may be obtained without a significant increase in driving voltage.
[0221] Host in the near-infrared emitting layer
[0222] The host may include a compound represented by Formula 301:
[0223] Formula 301
[0224] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21
[0225] Wherein, in Formula 301,
[0226] Ar 301 Can be selected from substituted or unsubstituted C 5 -C 60 Carbocyclic groups and substituted or unsubstituted C 1 -C 60 Heterocyclic groups,
[0227] xb11 can be 1, 2 or 3,
[0228] L 301 Can be selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene group, substituted or unsubstituted C 3 -C 10 Cycloalkenylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 Arylene group, substituted or unsubstituted C 1 -C 60a heteroarylene group, a substituted or unsubstituted divalent non-aromatic fused polycyclic group, and a substituted or unsubstituted divalent non-aromatic fused heteropolycyclic group;
[0229] xb1 can be an integer from 0 to 5.
[0230] R 301 It can be selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a substituted or unsubstituted C 1 -C 60 Alkyl groups, substituted or unsubstituted C 2 -C 60 Alkenyl groups, substituted or unsubstituted C 2 -C 60 Alkynyl group, substituted or unsubstituted C 1 -C 60 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 Aryl group, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio group, substituted or unsubstituted C 1 -C 60 heteroaryl group, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic 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 ) and -P(=O)(Q 301 )(Q 302 ),as well as
[0231] xb21 can be an integer from 1 to 5,
[0232] Where Q 301 To Q 303 Can be independently selected from C 1 -C 10 Alkyl group, C 1 -C 10 An alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but the embodiment is not limited thereto.
[0233] In an embodiment, in Formula 301, Ar 301 Can be selected from
[0234] naphthyl group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, group, a naphthacene group, a phenanthrene group, a perylene group, a pentaphenyl group, an indenoanthracene group, a dibenzofuran group, and a dibenzothiophene group; and
[0235] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, -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 ) and -P(=O)(Q 31 )(Q 32 ) is at least one substituted naphthyl group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, group, a naphthacene group, a phenanthrene group, a perylene group, a pentaphenyl group, an indenoanthracene group, a dibenzofuran group and a dibenzothiophene group,
[0236] Where Q 31 To Q 33 Can be independently selected from C 1 -C 10 Alkyl group, C 1 -C 10An alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but the embodiment is not limited thereto.
[0237] When xb11 in Formula 301 is 2 or greater than 2, at least two Ar 301 Can bind via a single bond.
[0238] In one or more than one embodiments, the compound represented by Formula 301 can be represented by Formula 301-1 or Formula 301-2:
[0239] Formula 301-1
[0240]
[0241] Formula 301-2
[0242]
[0243] Among them, in Formula 301-1 and Formula 301-2,
[0244] A 301 To A 304 can be independently selected from a benzene group, a naphthalene group, a phenanthrene group, a fluoranthene group, a triphenylene group, a pyrene group, group, a pyridine group, a pyrimidine group, an indene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, an indole group, a carbazole group, a benzocarbazole group, a dibenzocarbazole group, a furan group, a benzofuran group, a dibenzofuran group, a naphthofuran group, a benzonaphthofuran group, a dinaphthofuran group, a thiophene group, a benzothiophene group, a dibenzothiophene group, a naphthothiophene group, a benzonaphthothiophene group, and a dinaphthothiophene group,
[0245] X 301 Can be O, S or N-[(L 304 ) xb4 -R 304 ],
[0246] R 311 To R 314 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),
[0247] xb22 and xb23 can each independently be 0, 1 or 2,
[0248] L 301 、xb1、R 301 and Q 31 To Q 33 can be understood by reference to the description thereof provided herein, respectively,
[0249] L 302 To L 304 Each can be referred to by reference to the L 301 To understand the description,
[0250] xb2 to xb4 may each be understood by referring to the description of xb1 provided herein,
[0251] R 302 To R 304 Each can be referred to by referring to the R 301 description to understand.
[0252] In some embodiments, in Formula 301, Formula 301-1, and Formula 301-2, L 301 To L 304 can be independently selected from
[0253] a phenylene group, a naphthylene group, a fluorenylene group, a spiro-difluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthrylene group, a fluoranthenylene group, a phenylene group, a pyrenyl ... a phenylene group, a perylene group, a pentphenylene group, a hexaphenylene group, a pentphenylene group, a thienylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranyl group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group , pyrazinylene groups, pyrimidinylene groups, pyridazinylene groups, triazinylene groups, quinolinylene groups, isoquinolinylene groups, benzoquinolinylene groups, phthalazinylene groups, naphthyridinylene groups, quinoxalinylene groups, quinazolinylene groups, cinnolinylene groups, phenanthridinylene groups, acridinylene groups, phenanthrolinylene groups, phenazinylene groups, benzimidazolylene groups, isobenzothiazolylene groups, benzoxazolylene groups, isobenzoxazolylene groups, triazolylene groups, tetrazolylene groups, imidazopyridinylene groups, imidazopyrimidinylene groups, and azacarbazolylene groups; and
[0254] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzothioyl group, a pyridyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolyl group, isoquinolyl group, benzoquinolyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, -Si(Q31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ) is at least one substituted phenylene group, naphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenyl group, anthracenylene group, fluoranthenylene group, phenylphenanthrenyl group, pyrenylene ... a phenylene group, a perylene group, a pentphenylene group, a hexaphenylene group, a pentphenylene group, a thienylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranyl group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, a quinolylene group, an isoquinolylene group, a benzoquinolylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an imidazopyridylene group, an imidazopyrimidinylene group, and an azacarbazolylene group,
[0255] Where Q 31 To Q 33 Each can be understood by referring to the description thereof provided herein.
[0256] In some embodiments, in Formula 301, Formula 301-1, and Formula 301-2, R 301 To R 304 can be independently selected from
[0257] a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzothioyl group, a pyridyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group , pyrazinyl groups, pyrimidinyl groups, pyridazinyl groups, triazinyl groups, quinolyl groups, isoquinolyl groups, benzoquinolyl groups, phthalazinyl groups, naphthyridinyl groups, quinoxalinyl groups, quinazolinyl groups, cinnolinyl groups, phenanthridinyl groups, acridinyl groups, phenanthrolinyl groups, phenazinyl groups, benzimidazolyl groups, isobenzothiazolyl groups, benzoxazolyl groups, isobenzoxazolyl groups, triazolyl groups, tetrazolyl groups, imidazopyridinyl groups, imidazopyrimidinyl groups, and azacarbazolyl groups; and
[0258] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzothioyl group, a pyridyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolyl group, isoquinolyl group, benzoquinolyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, -Si(Q 31 )(Q 32 )(Q33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ) is at least one substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a phenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzothioyl group, a pyridyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group a benzoxazolyl group, a benzoxazolyl group, a benzoxazolyl group, a triazolyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group,
[0259] Where Q 31 To Q 33 Each can be understood by referring to the description thereof provided herein.
[0260] In some embodiments, the host may include an alkaline earth metal complex. For example, the host may include an aluminum (Al) complex (e.g., Alq), a beryllium (Be) complex (e.g., compound H55), a magnesium (Mg) complex, or a zinc (Zn) complex.
[0261] The host may include at least one selected from 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane (BCPDS), (4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenyl-phosphine oxide (POPCPA), and Compounds H1 to H55, but the embodiment is not limited thereto:
[0262]
[0263]
[0264]
[0265] In some embodiments, the host may include at least one selected from a silicon-containing compound (eg, BCPDS, etc., used in Examples) and a phosphine oxide-containing compound (eg, POPCPA, etc., used in Examples).
[0266] The host may include only one type (or kind) of compound or two or more types (or kinds) of compounds (eg, the constituent host in the example is BCPDS and POPCPA). As such, the embodiment may be modified in various suitable ways.
[0267] In some embodiments, the host may not be Compound A, Compound B, Compound C (Alq 3 ) or any of compound D(CBP):
[0268]
[0269] Electron transport region in the organic layer 150
[0270] The electron transport region may have: i) a single-layer structure composed of a single layer composed of a single material, ii) a single-layer structure composed of a single layer containing a plurality of different materials, or iii) a multi-layer structure each having a plurality of layers each containing a plurality of different materials.
[0271] The electron transport region may include at least one selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer, but the embodiment is not limited thereto.
[0272] In some embodiments, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein the layers of each structure are stacked in sequence on the near-infrared light-emitting layer in a prescribed order, but the embodiments are not limited thereto.
[0273] The electron transport region (eg, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound including at least one π-electron-depleted nitrogen-containing ring.
[0274] As used herein, the term "π-electron-depleted nitrogen-containing ring" refers to a C-containing ring having at least one *-N=*' moiety as a ring-forming part. 1 -C 60 Heterocyclic group.
[0275] For example, the “π-electron-depleted nitrogen-containing ring” may be i) a 5- to 7-membered heteromonocyclic group having at least one *-N=*' moiety, ii) a heteropolycyclic group in which at least two 5- to 7-membered heteromonocyclic groups, each having at least one *-N=*' moiety, are fused, or iii) a heteropolycyclic group in which at least one of the 5- to 7-membered heteromonocyclic groups, each having at least one *-N=*' moiety, is fused to at least one C 5 -C 60 A heteropolycyclic group to which carbocyclic groups are fused (eg, bonded together).
[0276] Examples of π-electron-depleted nitrogen-containing rings may include imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, indazole, purine, quinoline, isoquinoline, benzoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, phenanthridine, acridine, phenanthroline, phenazine, benzimidazole, isobenzothiazole, benzoxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine and azacarbazole, but the embodiment is not limited thereto.
[0277] In some embodiments, the electron transport region may include a compound represented by Formula 601:
[0278] Formula 601
[0279] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21
[0280] Wherein, in Formula 601,
[0281] Ar 601Can be selected from substituted or unsubstituted C 5 -C 60 Carbocyclic groups and substituted or unsubstituted C 1 -C 60 Heterocyclic groups,
[0282] xe11 can be 1, 2 or 3,
[0283] L 601 Can be selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene group, substituted or unsubstituted C 3 -C 10 Cycloalkenylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 Arylene group, substituted or unsubstituted C 1 -C 60 a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0284] xe1 can be an integer from 0 to 5,
[0285] R 601 Can be selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 Aryl group, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio group, substituted or unsubstituted C 1 -C 60 heteroaryl group, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 601 )(Q 602 )(Q 603 )、-C(=O)(Q601 )、-S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ),
[0286] Where Q 601 To Q 603 Can be independently C 1 -C 10 Alkyl group, C 1 -C 10 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group, and
[0287] xe21 can be an integer from 1 to 5.
[0288] In an embodiment, the number of Ar selected from xe11 601 and xe21 number of R 601 At least one of the may comprise a π-electron-depleted nitrogen-containing ring.
[0289] In an embodiment, in Formula 601, Ar 601 Can be selected from
[0290] phenyl group, naphthalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenanthene group, phenanthrenes group, anthracene group, fluoranthene group, triphenylene group, pyrene group, a tetraphenyl group, a phenanthracene group, a perylene group, a pentaphenyl group, an indenoanthracene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group; and
[0291] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, -Si(Q 31 )(Q32 )(Q 33 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ) is at least one substituted phenyl group, naphthyl group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenanthene group, phenanthrenyl group, anthracene group, fluoranthene group, triphenylene group, pyrene group, group, a naphthacene group, a phenanthracene group, a perylene group, a pentaphenyl group, an indenoanthracene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group,
[0292] Where Q 31 To Q 33 Can be independently selected from C 1 -C 10 Alkyl group, C 1 -C 10 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.
[0293] When xe11 in Formula 601 is 2 or greater than 2, at least two Ar 601 Can bind via a single bond.
[0294] In one or more than one embodiment, Ar in Formula 601 601 It may be an anthracene group.
[0295] In some embodiments, the compound represented by Formula 601 can be represented by Formula 601-1:
[0296] Formula 601-1
[0297]
[0298] Among them, in formula 601-1,
[0299] X 614 Can be N or C (R 614 ), X 615 Can be N or C (R615 ), X 616 Can be N or C (R 616 ), selected from X 614 To X 616 At least one of may be N,
[0300] L 611 To L 613 Each can be independently identified by reference to the L 601 To understand the description,
[0301] xe611 to xe613 can each be independently understood by referring to the description of xe1 provided herein,
[0302] R 611 To R 613 Each can be independently identified by reference to the R 601 description to understand, and
[0303] R 614 To R 616 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.
[0304] In the embodiment, in Formula 601 and Formula 601-1, L 601 and L 611 To L 613 Can be independently selected from:
[0305] a phenylene group, a naphthylene group, a fluorenylene group, a spiro-difluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthrylene group, a fluoranthenylene group, a phenylene group, a pyrenyl ... a phenylene group, a perylene group, a pentphenylene group, a hexaphenylene group, a pentphenylene group, a thienylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranyl group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group , pyrazinylene groups, pyrimidinylene groups, pyridazinylene groups, triazinylene groups, quinolinylene groups, isoquinolinylene groups, benzoquinolinylene groups, phthalazinylene groups, naphthyridinylene groups, quinoxalinylene groups, quinazolinylene groups, cinnolinylene groups, phenanthridinylene groups, acridinylene groups, phenanthrolinylene groups, phenazinylene groups, benzimidazolylene groups, isobenzothiazolylene groups, benzoxazolylene groups, isobenzoxazolylene groups, triazolylene groups, tetrazolylene groups, imidazopyridinylene groups, imidazopyrimidinylene groups, and azacarbazolylene groups; and
[0306] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzothioyl group, a pyridyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a benzoquinoline group, a The invention also includes a phenylene group substituted by at least one of a phthalazinyl group, a naphthyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group and an azacarbazolyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracene group, a fluoranthenyl group, a phenylene group, a pyrenyl ... a phenylene group, a perylene group, a pentphenylene group, a hexaphenylene group, a pentphenylene group, a thienylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranyl group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group, a pyrazinylene group The invention also includes a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group, but the embodiment is not limited thereto.
[0307] In one or more than one embodiments, in Formula 601 and Formula 601-1, xe1 and xe611 to xe613 can each independently be 0, 1 or 2.
[0308] In one or more than one embodiments, in Formula 601 and Formula 601-1, R 601 and R 611 To R 613 Can be independently selected from:
[0309] a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzothioyl group, a pyridyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group a benzoxazolyl group, a benzoxazolyl group, a benzoxazolyl group, a triazine group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group;
[0310] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzothioyl group, a pyridyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a benzoquinoline group, a a phenyl group substituted by at least one of a benzoimidazole group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group and an azacarbazolyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzothioyl group, a pyridyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group , pyrazinyl groups, pyrimidinyl groups, pyridazinyl groups, triazinyl groups, quinolyl groups, isoquinolyl groups, benzoquinolyl groups, phthalazinyl groups, naphthyridinyl groups, quinoxalinyl groups, quinazolinyl groups, cinnolinyl groups, phenanthridinyl groups, acridinyl groups, phenanthrolinyl groups, phenazinyl groups, benzimidazolyl groups, isobenzothiazolyl groups, benzoxazolyl groups, isobenzoxazolyl groups, triazolyl groups, tetrazolyl groups, imidazopyridinyl groups, imidazopyrimidinyl groups, and azacarbazolyl groups; and
[0311] -S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ),
[0312] Where Q 601 and Q 602 Each can be understood independently by reference to the description thereof provided herein.
[0313] The electron transport region may include at least one compound selected from Compound ET1 to Compound ET36, but the embodiment is not limited thereto:
[0314]
[0315]
[0316]
[0317]
[0318] In one or more than one embodiment, the electron transport region may include a selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq 3 , BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ) and NTAZ:
[0319]
[0320] The thickness of the buffer layer, hole blocking layer or electron control layer may be independently about to about In some embodiments, the range is about to about When the thickness of the buffer layer, the hole blocking layer, or the electron control layer is within any of these ranges, excellent hole blocking characteristics or excellent electron control characteristics may be obtained without a significant increase in driving voltage.
[0321] The thickness of the electron transport layer can be about to about In some embodiments, the range is about to about When the thickness of the electron transport layer is within any of these ranges, excellent electron transport characteristics may be obtained without a significant increase in driving voltage.
[0322] The electron transport region (eg, an electron transport layer in the electron transport region) may further include a material including a metal in addition to the materials described above.
[0323] The material containing metal may include at least one selected from alkali metal complex and alkaline earth metal complex. The alkali metal complex may include metal ions selected from lithium (Li) ions, sodium (Na) ions, potassium (K) ions, rubidium (Rb) ions and cesium (Cs) ions. The alkaline earth metal complex may include metal ions selected from beryllium (Be) ions, magnesium (Mg) ions, calcium (Ca) ions, strontium (Sr) ions and barium (Ba) ions. Each ligand coordinated with the metal ions of the alkali metal complex and the alkaline earth metal complex may be independently selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline and cyclopentadiene, but the embodiment is not limited thereto.
[0324] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (LiQ) or compound ET-D2:
[0325]
[0326] The electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 190. The electron injection layer may be in direct contact with (eg, in physical contact with) the second electrode 190.
[0327] The electron injection layer may have: i) a single-layer structure composed of a single layer composed of a single material, ii) a single-layer structure composed of a single layer containing a plurality of different materials, or iii) a multi-layer structure having a plurality of layers each containing a plurality of different materials.
[0328] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or a combination thereof.
[0329] In some embodiments, the electron injection layer may include Li, Na, K, Rb, Cs, Mg, Ca, Er, Tm, Yb, or any combination thereof, but the embodiments are not limited thereto.
[0330] The alkali metal may be selected from Li, Na, K, Rb and Cs. In an embodiment, the alkali metal may be Li, Na or Cs. In one or more than one embodiments, the alkali metal may be Li or Cs, but the embodiment is not limited thereto.
[0331] The alkaline earth metal may be selected from Mg, Ca, Sr and Ba.
[0332] The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb and Gd.
[0333] The alkali metal compound, alkaline earth metal compound, and rare earth metal compound can each independently be selected from the oxides and halides (e.g., fluorides, chlorides, bromides, and / or iodides) of alkali metals, alkaline earth metals, and rare earth metals, respectively.
[0334] The alkali metal compound can be selected from alkali metal oxides (e.g., Li 2 O, Cs 2 O, or K 2 O) and alkali metal halides (e.g., LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI). In an embodiment, the alkali metal compound can be selected from LiF, Li 2 O, NaF, LiI, NaI, CsI, and KI, but the embodiment is not limited thereto.
[0335] The alkaline earth metal compound can be selected from alkaline earth metal oxides, such as BaO, SrO, CaO, Ba x Sr 1-x O (where 0 < x < 1) and Ba x Ca 1-x O (where 0 < x < 1). In an embodiment, the alkaline earth metal compound can be selected from BaO, SrO, and CaO, but the embodiment is not limited thereto.
[0336] The rare earth metal compound can be selected from YbF 3 、ScF 3 、Sc 2 O 3 、Y 2 O 3 、Ce 2 O 3 、GdF 3 and TbF 3 。 In an embodiment, the rare earth metal compound can be selected from YbF 3 、ScF 3 、TbF 3 、YbI 3 、ScI 3 and TbI 3 , but the embodiment is not limited thereto.
[0337] Alkali metal complex, alkaline earth metal complex and rare earth metal complex can each include the ions of alkali metal, alkaline earth metal and rare earth metal described above. Each ligand coordinated with the metal ion of alkali metal complex, alkaline earth metal complex and rare earth metal complex can be independently selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline and cyclopentadiene, but embodiment is not limited thereto.
[0338] The electron injection layer can be composed of the alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex or its combination described above. In some embodiments, the electron injection layer can further include organic material. When the electron injection layer further includes organic material, alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex or its combination can be evenly or non-uniformly dispersed in the matrix including organic material.
[0339] The thickness of the electron injection layer can be about to about In some embodiments, the range is about to about When the thickness of the electron injection layer is within any of these ranges, excellent electron injection characteristics may be obtained without a significant increase in driving voltage.
[0340] In an embodiment, the electron transport region in the near-infrared light-emitting diode 10 may include a buffer layer, an electron transport layer, and an electron injection layer, and
[0341] At least one of the electron transport layer and the electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or a combination thereof.
[0342] The second electrode 190
[0343] The second electrode 190 may be on the organic layer 150. In an embodiment, the second electrode 190 may be a cathode, which is an electron injection electrode. In this embodiment, the material used to form the second electrode 190 may be a material having a low work function, for example, a metal, an alloy, a conductive compound, or a mixture thereof.
[0344] The second electrode 190 may include at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ITO and IZO, but the embodiment is not limited thereto. The second electrode 190 may be a transmissive electrode, a semi-transmissive electrode or a reflective electrode.
[0345] The second electrode 190 may have a single-layer structure, or a multi-layer structure including two or more layers.
[0346] In an embodiment, at least one of the hole transport region, the near-infrared light emitting layer, and the electron transport region (eg, the hole transport region and the near-infrared light emitting layer) may include a carbazole-containing compound.
[0347] In some embodiments, the organic layer 150 may include a visible light emitting layer that can emit visible light. Therefore, the near-infrared light emitting diode 10 can emit visible light (e.g., red light, green light, and / or blue light) in addition to near-infrared light. In some embodiments, in addition to the near-infrared light emitting layer described herein, the organic layer 150 may further include a red emission layer patterned with red sub-pixels, a green emission layer patterned with green sub-pixels, and a blue emission layer patterned with blue sub-pixels.
[0348] The layers constituting the organic layer 150 may be formed in certain regions by using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser induced thermal imaging (LITI).
[0349] When the layers included in the organic layer 150 are each independently formed by vacuum deposition, the deposition temperature may be in the range of about 100° C. to about 500° C. ... -8 To about 10 -3 The vacuum degree in the torr range and the to about Vacuum deposition is performed at a deposition rate in a range of 200 nm.
[0350] When the layers included in the organic layer 150 are each independently formed by spin coating, the spin coating can be performed at a coating rate of about 2,000 revolutions per minute (rpm) to about 5,000 rpm and at a heat treatment temperature of about 80° C. to about 200° C., depending on the compounds to be included in each layer and the structure of each layer to be formed.
[0351] Device
[0352] The aforementioned near infrared light emitting diodes can be applied to various suitable devices.Thus, according to one or more embodiments, a device can include a near infrared light emitting diode.
[0353] In an embodiment, in addition to the near-infrared light emitting diode, the device may further include a visible light emitting diode including a first electrode, a second electrode, and a visible light emitting layer between the first electrode and the second electrode.
[0354] In one or more embodiments, the device may further include a sensor configured to identify near infrared light reflected from an object exposed to at least a portion of the near infrared light emitted by the near infrared light emitting diode.
[0355] In embodiments, the object may be a part of a human body (eg, a fingerprint, a pupil, etc.).
[0356] In one or more embodiments, in addition to the near-infrared light-emitting diode described above, the device may further include a thin film transistor (TFT) including a source electrode and a drain electrode. One of the source electrode and the drain electrode of the TFT may be electrically connected to one of the first electrode and the second electrode of the near-infrared light-emitting diode.
[0357] Such devices can be applied to various suitable purposes.In some embodiments, the device can be a transmitting device, an authentication device or an electronic device.
[0358] The emitting device can be used for various suitable displays, light sources, etc.
[0359] The authentication device may be, for example, a biometric authentication device that authenticates an individual based on biometric information (eg, fingertips, pupils, etc.).
[0360] The authentication device may further include a biometric information acquisition unit (eg, a sensor configured to identify near infrared light reflected from an object exposed to at least a portion of the near infrared light emitted by the near infrared light emitting diode).
[0361] The electronic device can be applied to personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notes, electronic dictionaries, electronic game consoles, medical devices (e.g., electronic thermometers, blood pressure meters, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram recorders, ultrasonic diagnostic devices, endoscopic display devices), fish finders, various suitable measuring devices, instruments (e.g., instruments for cars, airplanes, and ships), projectors, but the implementation scheme is not limited to these.
[0362] General definition of at least some substituents
[0363] As used herein, the term “C 1 -C 60 The term "alkyl group" refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms. Examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isopentyl group, and a hexyl group. In some embodiments, C 1 -C 60 The alkyl group may be C 1 -C 30 Alkyl group, C 1 -C 20 Alkyl group or C 1 -C 10 As used herein, the term "C 1 -C 60 "Alkylene group" refers to a group having 1 -C 60 Alkyl groups are divalent groups of substantially the same structure.
[0364] As used herein, the term “C 2 -C 60 "Alkenyl group" means a 2 -C 60 The main chain (e.g., in the middle) or the end (e.g., at the terminal) of the alkyl group has at least one carbon-carbon double bond. Examples thereof include vinyl groups, propenyl groups, and butenyl groups. In some embodiments, C 2 -C 60 The alkenyl group may be C 2 -C 30 Alkenyl group, C 2 -C 20 Alkenyl group or C 2 -C 10 As used herein, the term "C 2 -C 60 "Alkenylene group" refers to a 2 -C 60 Alkenyl groups are divalent groups of substantially the same structure.
[0365] As used herein, the term “C 2 -C 60 "Alkynyl group" means a 2 -C 60 The main chain (e.g., in the middle) or the end (e.g., at the terminal) of the alkyl group has at least one hydrocarbon group with a carbon-carbon triple bond. Examples thereof include ethynyl groups and propynyl groups. In some embodiments, C 2 -C 60 The alkynyl group may be C 2 -C30 Alkynyl group, C 2 -C 20 Alkynyl group or C 2 -C 10 As used herein, the term "C 2 -C 60 "Alkyne group" refers to a 2 -C 60 Alkynyl groups are divalent radicals of substantially the same structure.
[0366] As used herein, the term “C 1 -C 60 "Alkoxy group" refers to a group consisting of -OA 101 (A 101 C 1 -C 60 Examples thereof include a methoxy group, an ethoxy group, and an isopropoxy group.
[0367] As used herein, the term “C 3 -C 10 A "cycloalkyl group" refers to a monovalent saturated hydrocarbon monocyclic group containing 3 to 10 carbon atoms. Examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. As used herein, the term "C 3 -C 10 "Cycloalkylene group" refers to a group having 3 -C 10 Cycloalkyl groups are divalent groups of substantially the same structure.
[0368] As used herein, the term “C 1 -C 10 The term "heterocycloalkyl group" refers to a monovalent monocyclic group containing at least one heteroatom (e.g., 1, 2, 3, 4 or 5 heteroatoms) selected from N, O, Si, P and S as a ring-forming atom and 1 to 10 carbon atoms. Examples thereof include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group and a tetrahydrothienyl group. As used herein, the term "C 1 -C 10 "Heterocycloalkylene group" refers to a group having a 1 -C 10 Heterocycloalkyl groups are divalent groups of substantially the same structure.
[0369] As used herein, the term “C 3 -C 10A "cycloalkenyl group" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one double bond in its ring and not being aromatic (e.g., the ring and / or the group are not aromatic). Examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. As used herein, the term "C 3 -C 10 "Cycloalkenylene group" refers to a group having a 3 -C 10 Cycloalkenyl groups are divalent groups of substantially the same structure.
[0370] As used herein, the term “C 1 -C 10 The term "heterocycloalkenyl group" refers to a monovalent monocyclic group containing at least one heteroatom (e.g., 1, 2, 3, 4 or 5 heteroatoms) selected from N, O, Si, P and S as a ring atom, 1 to 10 carbon atoms and at least one double bond in its ring. 1 -C 10 Examples of heterocycloalkenyl groups include 4,5-dihydro-1,2,3,4-oxatriazolyl groups, 2,3-dihydrofuranyl groups and 2,3-dihydrothienyl groups. 1 -C 10 The term "heterocycloalkenylene group" refers to a 1 -C 10 Heterocycloalkenyl groups are divalent groups of substantially the same structure.
[0371] As used herein, the term “C 6 -C 60 "Aryl group" refers to a monovalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms. As used herein, "C 6 -C 60 The term "arylene group" refers to a divalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms. 6 -C 60 Examples of the aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group and When C 6 -C 60 Aryl groups and C 6 -C 60 When each arylene group independently comprises two or more rings, the rings may be fused (eg, bonded together). 6 -C 60 The aryl group may be C 6 -C 30 Aryl group, C 6 -C 18 Aryl group or C 6 -C12 In some embodiments, C 6 -C 60 The arylene group may be C 6 -C 30 Arylene group, C 6 -C 18 Arylene group or C 6 -C 12 Arylene group.
[0372] As used herein, the term “C 1 -C 60 The term "heteroaryl group" refers to a monovalent group having a heterocyclic aromatic system containing at least one heteroatom (e.g., 1 to 20, 1 to 15 or 1 to 10, such as 1, 2, 3, 4, 5 or 6 heteroatoms) selected from N, O, Si, P and S as a ring atom and 1 to 60 carbon atoms. As used herein, the term "C 1 -C 60 The term "heteroarylene group" refers to a divalent group having a heterocyclic aromatic system containing at least one heteroatom (e.g., 1 to 20, 1 to 15 or 1 to 10, e.g., 1, 2, 3, 4, 5 or 6 heteroatoms) selected from N, O, Si, P and S as a ring atom and 1 to 60 carbon atoms. 1 -C 60 Examples of the heteroaryl group include a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group and an isoquinolyl group. 1 -C 60 Heteroaryl groups and C 1 -C 60 When each heteroarylene group independently comprises two or more rings, the rings may be fused (eg, joined together). 1 -C 60 The heteroaryl group may be C 1 -C 30 Heteroaryl groups, C 1 -C 18 Heteroaryl groups or C 1 -C 12 In some embodiments, C 1 -C 60 The heteroarylene group can be C 1 -C 30 Heteroarylene group, C 1 -C 18 Heteroarylene group or C 1 -C 12 Heteroarylene groups.
[0373] As used herein, the term “C6 -C 60 The aryloxy group is represented by -OA 102 (A 102 C 6 -C 60 As used herein, the term "C 6 -C 60 The arylthio group is represented by -SA 103 (A 103 C 6 -C 60 Aryl group) represents.
[0374] As used herein, the term "monovalent non-aromatic fused polycyclic group" refers to a monovalent group having two or more rings that are fused (e.g., bound together) and having only carbon atoms as ring atoms (e.g., 8 to 60 carbon atoms, such as 10, 20, 30, 40 or 50 carbon atoms), wherein the entire molecular structure is non-aromatic. An example of a monovalent non-aromatic fused polycyclic group may be a fluorenyl group. As used herein, the term "divalent non-aromatic fused polycyclic group" refers to a divalent group having substantially the same structure as a monovalent non-aromatic fused polycyclic group.
[0375] As used herein, the term "monovalent non-aromatic fused heteropolycyclic group" refers to a monovalent group having two or more fused rings and having at least one heteroatom (e.g., 1 to 20, 1 to 15 or 1 to 10, such as 1, 2, 3, 4, 5 or 6 heteroatoms) selected from N, O, Si, P and S other than carbon atoms (e.g., 1 to 60 carbon atoms, such as 10, 20, 30, 40 or 50 carbon atoms) as a ring-forming atom, wherein the entire molecular structure is non-aromatic. An example of a monovalent non-aromatic fused heteropolycyclic group may be a carbazolyl group. As used herein, the term "divalent non-aromatic fused heteropolycyclic group" refers to a divalent group having substantially the same structure as a monovalent non-aromatic fused heteropolycyclic group.
[0376] As used herein, the term “C 5 -C 60 "Carbocyclic group" refers to a monocyclic or polycyclic group having only 5 to 60 carbon atoms as ring atoms. 5 -C 60 The carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. 5 -C 60 A "carbocyclic group" refers to a ring (e.g., a benzene group), a monovalent group (e.g., a phenyl group), or a divalent group (e.g., a phenylene group). In addition, depending on the group attached to the C 5 -C 60 The number of substituents in a carbocyclic group, C5 -C 60 The carbocyclic group may be a trivalent group or a tetravalent group.
[0377] As used herein, the term “C 1 -C 60 "Heterocyclic group" refers to a 5 -C 60 The carbocyclic group is a group having substantially the same structure as the carbocyclic group, but in addition to carbon atoms (e.g., 1 to 60 carbon atoms), at least one heteroatom (e.g., 1 to 20, 1 to 15 or 1 to 10, such as 1, 2, 3, 4, 5 or 6 heteroatoms) selected from N, O, Si, P and S is used as a ring-forming atom.
[0378] In this specification, substituted C 5 -C 60 Carbocyclyl groups, substituted C 1 -C 60 Heterocyclic groups, substituted C 3 -C 10 Cycloalkylene groups, substituted C 1 -C 10 Heterocycloalkylene groups, substituted C 3 -C 10 Cycloalkenylene groups, substituted C 1 -C 10 Heterocycloalkenylene groups, substituted C 6 -C 60 Arylene groups, substituted C 1 -C 60 Heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C 1 -C 60 Alkyl groups, substituted C 2 -C 60 Alkenyl groups, substituted C 2 -C 60 Alkynyl groups, substituted C 1 -C 60 Alkoxy groups, substituted C 3 -C 10 Cycloalkyl groups, substituted C 1 -C 10 Heterocycloalkyl groups, substituted C 3 -C 10 Cycloalkenyl groups, substituted C 1 -C 10 Heterocycloalkenyl groups, substituted C 6 -C 60 Aryl groups, substituted C 6 -C 60Aryloxy groups, substituted C 6 -C 60 Arylthio groups, substituted C 1 -C 60 At least one substituent of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group may be selected from:
[0379] Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl groups and C 1 -C 60 Alkoxy groups;
[0380] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 ) and -P(=O)(Q 11 )(Q 12 ) at least one substituted C 1 -C 60 Alkyl group, C 2 -C60 Alkenyl group, C 2 -C 60 Alkynyl groups and C 1 -C 60 Alkoxy groups;
[0381] C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heteropolycyclic groups, biphenyl groups, and terphenyl groups;
[0382] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy groups, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 ) and -P(=O)(Q 21 )(Q 22 ) at least one substituted C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups; and
[0383] -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 ) and -P(=O)(Q 31 )(Q 32 ),
[0384] Where Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2-C 60 Alkynyl group, C 1 -C 60 Alkoxy groups, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 1 -C 60 Alkyl substituted C 6 -C 60 Aryl group, C 6 -C 60 Aryl-substituted C 6 -C 60 Aryl group, terphenyl group, C 1 -C 60 Heteroaryl groups, C 1 -C 60 Alkyl substituted C 1 -C 60 Heteroaryl groups, C 6 -C 60 Aryl-substituted C 1 -C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups and monovalent non-aromatic fused heteropolycyclic groups.
[0385] As used herein, the term "Ph" refers to a phenyl group, as used herein, the term "Me" refers to a methyl group, as used herein, the term "Et" refers to an ethyl group, as used herein, the term "ter-Bu" or "Bu" refers to an ethyl group. t " represents a tert-butyl group, and as used herein, the term "OMe" represents a methoxy group.
[0386] As used herein, the term "biphenyl group" refers to a phenyl group substituted by at least one phenyl group. 6 -C 60 "substituted phenyl group" having an aryl group as a substituent.
[0387] As used herein, the term "terphenyl group" refers to a phenyl group substituted by at least one biphenyl group. 6 -C 60 Aryl-substituted C 6 -C 60"substituted phenyl group" having an aryl group as a substituent.
[0388] Unless otherwise defined, as used herein, the symbols * and *' refer to sites of attachment to adjacent atoms in a formula.
[0389] Hereinafter, compounds and organic light-emitting devices according to one or more embodiments will be described in more detail with reference to Examples. The expression "using B instead of A" used in describing a synthesis example means replacing A with the same number of molar equivalents of B.
[0390] Example
[0391] Example 1
[0392] An indium tin oxide (ITO) film (anode) was formed on a glass substrate to a thickness of 120 nm. The anode was then ultrasonically cleaned and pretreated (UV-O 3 treatment and heat treatment).
[0393] Compound HT5 was deposited on the anode to form a hole transport layer having a thickness of 120 nm.
[0394] Then, the main body (Alq 3 ) and a dopant (Compound 3, 1 wt %) were co-deposited to form a near-infrared light-emitting layer having a thickness of 30 nm.
[0395] Then, BAlq was deposited on the near-infrared light emitting layer to form a buffer layer having a thickness of 5 nm. 3 Deposited on the buffer layer to form an electron transport layer having a thickness of 25 nm. Then, LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 0.5 nm. Finally, aluminum (Al) was deposited on the electron injection layer to form a cathode having a thickness of 150 nm, thereby completing a structure having glass / ITO (120 nm) / HT5 (120 nm) / host: dopant (1 wt%, 30 nm) / BAlq (5 nm) / Alq 3 Fabrication of a light-emitting device with a structure of (25nm) / LiF(0.5nm) / Al(150nm).
[0396]
[0397] Examples 2 to 6 and Comparative Example B
[0398] Light-emitting devices according to Examples 2 to 6 and Comparative Example B were manufactured in substantially the same manner as in Example 1, except that the dopant materials shown in Table 1 were used for the respective near-infrared light-emitting layers.
[0399] Evaluation Example 1
[0400] Each of the light emitting devices prepared according to Examples 1 to 6 and Comparative Example B was evaluated using a Keithley 236 source measurement unit (SMU) and a PR650 luminance meter at 5 mA / cm 2 The service life under the current density (T 95 ) and the maximum emission wavelength. The results are shown in Table 1. Service life (T 95 ) represents the time (hours) for the brightness of each light-emitting device to decrease to 95% of its initial brightness.
[0401] Table 1
[0402]
[0403]
[0404]
[0405] Referring to Table 1, compared with the light emitting device according to Comparative Example B, it was found that the light emitting devices according to Examples 1 to 6 emitted near infrared light while having a long lifetime.
[0406] As is apparent from the foregoing description, the near-infrared light emitting diode can emit near-infrared light and has a long lifetime.
[0407] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should be considered as available for other similar features or aspects in other embodiments.
[0408] It should be understood that although the terms "first", "second", "third", etc. can be used in this article to describe various elements, components, areas, layers and / or parts, these elements, components, areas, layers and / or parts should not be limited to these terms. These terms are used to distinguish one element, component, area, layer and / or part from another element, component, area, layer and / or part. Therefore, without departing from the spirit and scope of the present disclosure, the first element, component, area, layer or part described above can be referred to as the second element, component, area, layer or part.
[0409] Spatially relative terms, such as "under", "lower", "lower", "below", "above", "upper", etc., may be used herein to describe the relationship of one element or feature to another element or feature for ease of explanation, as illustrated in the accompanying drawings. It should be understood that in addition to the directions described in the accompanying drawings, spatially relative terms are intended to also include different orientations of the device in use or operation. For example, if the device in the accompanying drawings is flipped, the elements described as being "under" or "under" or "below" other elements or features will be positioned "above" other elements or features. Therefore, the exemplary terms "under" and "below" can include both the upper and lower directions. The device can be oriented in other ways (e.g., rotated 90 degrees or in other directions), and the spatially relative descriptors used herein should be interpreted accordingly.
[0410] It should be understood that when an element or layer is referred to as being "on," "connected to," or "coupled to" another element or layer, it can be directly on, directly connected to, or directly coupled to another element or layer, or there can be one or more intervening elements or layers. In addition, it should be understood that when an element or layer is referred to as being "between" two elements or layers, it can be the only element or layer between the two elements or layers, or there can also be one or more intervening elements or layers.
[0411] The terms used herein are used only for the purpose of describing specific embodiments and are not intended to limit the present disclosure. As used herein, the singular forms "a" and "an" are intended to include the plural forms as well, unless the context clearly indicates otherwise. It should also be understood that the terms "comprises", "comprising", "includes" and "including", when used in this specification, indicate the presence of specified features, integers, behaviors, operations, elements and / or components, but do not exclude the presence or addition of one or more than one other features, integers, behaviors, operations, elements, components and / or groups thereof.
[0412] As used herein, the terms "substantially", "about" and similar terms are used as approximate terms rather than as terms of degree, and are intended to explain the inherent deviations in measured or calculated values, which are recognized by those of ordinary skill in the art. In addition, when describing an embodiment of the present disclosure, the use of "may" refers to "one or more than one embodiment of the present disclosure". As used herein, the terms "use", "using" and "used" may be considered to be synonymous with the terms "utilize", "utilizing" and "utilized", respectively. In addition, the term "exemplary" is intended to refer to an example or illustration.
[0413] In addition, any numerical range listed herein is intended to include all sub-ranges of the same numerical precision within the scope of the listing. For example, the range of "1.0 to 10.0" is intended to include all sub-ranges between the listed minimum value 1.0 and the listed maximum value 10.0 (and including the end value), that is, having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, for example, such as 2.4 to 7.6. Any maximum numerical value listed herein is intended to include all lower numerical limits included therein, and any minimum numerical value listed in this specification is intended to include all higher numerical limits included therein. Therefore, the applicant reserves the right to modify this specification (including claims) to explicitly list any sub-ranges included in the scope explicitly listed herein.
[0414] Although one or more embodiments have been described with reference to the accompanying drawings, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope as defined by the claims and their equivalents.
Claims
1. Near infrared light emitting diodes, including: a first electrode; a second electrode; as well as an organic layer between the first electrode and the second electrode, wherein the organic layer includes a near-infrared light-emitting layer, the near-infrared light-emitting layer includes an organometallic compound containing osmium, and the organometallic compound containing osmium is configured to emit near-infrared light having a maximum emission wavelength in a range of 680 nm or more and 3,000 nm or less, The osmium-containing organometallic compound is represented by Formula 1: Formula 1 M(L1) n1 (L2) n2 Among them, in formula 1, M is Os, L1 is selected from the ligand represented by formula 1-1: Formula 1-1 n1 is an integer from 1 to 4; and when n1 is 2 or greater, at least two L1 are the same as or different from each other, L2 is an organic ligand, n2 is an integer from 0 to 4; and when n2 is 2 or greater, at least two L2 are the same as or different from each other, i) at least two selected from n1 number of L1, ii) at least two selected from n2 number of L2, or iii) at least one selected from n1 number of L1 and at least one selected from n2 number of L2, optionally via a single bond, a double bond, *=N-*', *-N=*', *=C[(L3) a3 -(R3)]-*',*-C[(L3) a3 -(R3)] = *', *-N[(L3) a3 -(R3)]-*', *-B(R3)-*', *-P(R3)-*', *-C(R3)(R4)-*', *-Si(R3)(R4)-*', *-Ge(R3)(R4)-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R3)=*', *=C(R3)-*', *-C(R3)=C(R4)-*', *-C(=S)-*' or *-C≡C-*' to form a tridentate ligand, a tetradentate ligand, a pentadentate ligand or a hexadentate ligand, and * and *' each represent a site of attachment to an adjacent atom, Among them, in formula 1-1, Ring A1 and Ring A2 are each independently C5-C 30 Carbocyclic group or C1-C 30 Heterocyclic groups, Z 31 and Z 32 each independently represents a covalent bond, a coordinate bond, O, S, C(R7)(R8), Si(R7)(R8), N(R7), P(R7), C(R7)(R8)(R9), Si(R7)(R8)(R9), N(R7)(R8) or P(R7)(R8), X1 and X2 are each independently C or N, Ring A1 and T1; and T1 and Ring A2 are each independently bonded via a single bond or a double bond, T1 is a single bond, a double bond, *=N-*', *-N=*', *=C[(L5) a5 -(R5)]-*',*-C[(L5) a5 -(R5)] = *', *-N[(L5) a5 -(R5)]-*', *-B(R5)-*', *-P(R5)-*', *-C(R5)(R6)-*', *-Si(R5)(R6)-*', *-Ge(R5)(R6)-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R5)=*', *=C(R5)-*', *-C(R5)=C(R6)-*', *-C(=S)-*' or *-C≡C-*', wherein * and *' each represent a site of attachment to an adjacent atom, L3 and L5 are each independently a single bond, unsubstituted or substituted with at least one R 10 Substituted C5-C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10 Substituted C1-C 30 Heterocyclic groups, a3 and a5 are each independently an integer from 1 to 5, R1 to R 10 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a substituted or unsubstituted C1-C 60 Alkyl group, substituted or unsubstituted C2-C 60 Alkenyl group, substituted or unsubstituted C2-C 60 Alkynyl group, substituted or unsubstituted C1-C 60 Alkoxy groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkyl group, substituted or unsubstituted C3-C 10 Cycloalkenyl group, substituted or unsubstituted C1-C 10 Heterocycloalkenyl group, substituted or unsubstituted C6-C 60 Aryl group, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthio group, substituted or unsubstituted C1-C 60 heteroaryl group, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)2(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), Selected from R1 to R 10 Two adjacent groups in the optionally combined to form an unsubstituted or substituted group with at least one R 10a Substituted C5-C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a A substituted heterocyclic group, R 10a With R 10 The same definition, b1 and b2 are each independently an integer from 0 to 10, * 1 and* 2 Each represents a connection site with M in Formula 1, M and Z in formula 1-1 31 or X1 and the bond between M and Z in formula 1-1 32 or X2 are each independently a covalent bond or a coordination bond, and The substituted C1-C 60 Alkyl group, the substituted C2-C 60 Alkenyl group, the substituted C2-C 60 Alkynyl group, the substituted C1-C 60 Alkoxy group, the substituted C3-C 10 Cycloalkyl group, the substituted C1-C 10 Heterocycloalkyl group, the substituted C3-C 10 Cycloalkenyl group, the substituted C1-C 10 Heterocycloalkenyl group, the substituted C6-C 60 Aryl group, the substituted C6-C 60 Aryloxy group, the substituted C6-C 60 Arylthio group, the substituted C1-C 60 At least one substituent of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group is selected from: Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups and C1-C 60 Alkoxy groups; Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C1-C 60 heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)2(Q 11 )、-S(=O)2(Q 11 ) and -P(=O)(Q 11 )(Q 12 ) at least one substituted C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups and C1-C 60 Alkoxy groups; C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C1-C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heteropolycyclic groups, biphenyl groups, and terphenyl groups; Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group, C1-C 60 Alkoxy groups, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C1-C 60 heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)2(Q 21 )、-S(=O)2(Q 21 ) and -P(=O)(Q 21 )(Q 22 ) at least one substituted C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C1-C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups; and -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)2(Q 31 )、-S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ), Among them, Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group, C1-C 60 Alkoxy groups, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl groups, with at least one C1-C 60 Alkyl-substituted C6-C 60 Aryl group, with at least one C6-C 60 Aryl-substituted C6-C 60 Aryl group, terphenyl group, C1-C 60 Heteroaryl groups, with at least one C1-C 60 Alkyl-substituted C1-C 60 Heteroaryl groups, with at least one C6-C 60 Aryl-substituted C1-C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups and monovalent non-aromatic fused heteropolycyclic groups, Wherein L2 is selected from the ligands represented by Formula 4-1 to Formula 4-4: Among them, in Formula 4-1 to Formula 4-4, Y1 is C, P or As, Y 11 is O, N, N(Z 13 ), P(Z 13 )(Z 14 ), or As(Z 13 )(Z 14 ), Y 12 is O, N, N(Z 15 ), P(Z 15 )(Z 16 ), or As(Z 15 )(Z 16 ), T 11 For single bonds, double bonds, *-C(Z 11 )(Z 12 )-*'、*-C(Z 11 )(Z 12 )-C(Z 13 )(Z 14 )-*'、*-C(Z 11 )=C(Z 12 )-*'、*=C(Z 11 )-*'、*-C(Z 11 )=*'、*=C(Z 11 )-C(Z 12 )=C(Z 13 )-*'、*-C(Z 11 )=C(Z 12 )-C(Z 13 )=*'or*-N(Z 11 )-*', where * and *' each represent a connection site with an adjacent atom, *-C(Z 11 )=C(Z 12 )-*' 11 and Z 12 Optionally combined to form unsubstituted or substituted with at least one R 10a Substituted C5-C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C1-C 30 A heterocyclic group, and R 10a is defined as the same as that defined in Formula 1-1, Y 13 and Y 14 are each independently C or N, Y 17 C, N(Z 17 ) or P(Z 17 ), Ring A 11 C5-C 30 Carbocyclic group or C1-C 30 Heterocyclic groups, Z 11 and Z 13 To Z 17 Each is defined as the same as R1 defined in Formula 1-1, c11 is an integer from 0 to 10, and * and *' each independently represent a connection site with M in Formula 1, Among them, the formula 1-1 The moiety represented by is selected from the groups represented by formulae A1-1 to A1-52 and A1-54 to A1-56: Wherein in Formulas A1-1 to A1-52 and A1-54 to A1-56, X1 and R1 are respectively the same as those defined in Formula 1-1, b12 is an integer from 0 to 2, b13 is an integer from 0 to 3, b14 is an integer from 0 to 4, b15 is an integer from 0 to 5, b16 is an integer from 0 to 6, b17 is an integer from 0 to 7, *' represents the Z in formula 1-1 31 The attachment site, and * represents the connection site with T1 in Formula 1-1, Among them, the formula 1-1 The moiety represented by is selected from the groups represented by the formulae A2-1 to A2-32, A2-34 to A2-37, A2-39 and A2-41 to A2-50: Wherein in formulae A2-1 to A2-32, A2-34 to A2-37, A2-39 and A2-41 to A2-50, X2 and R2 are respectively the same as those defined in Formula 1-1, X 21 Selected from O, S, N (R 21 )、C(R 21 )(R 22 ) and Si(R 21 )(R 22 ), R 21 and R 22 Each is the same as defined in R2, b22 is an integer from 0 to 2, b23 is an integer from 0 to 3, b24 is an integer from 0 to 4, b25 is an integer from 0 to 5, b26 is an integer from 0 to 6, b27 is an integer from 0 to 7, *' represents the Z in formula 1-1 32 The attachment site, and * represents the bonding site with T1 in Formula 1-1. 2 . The near-infrared light emitting diode according to claim 1 , wherein the osmium-containing organometallic compound is neutral and is configured to emit near-infrared light having a maximum emission wavelength in a range of 700 nm or more and 850 nm or less. The near-infrared light-emitting diode as claimed in claim 1 , wherein T1 is a single bond.
4. The near-infrared light emitting diode as claimed in claim 1, wherein R1 to R6 and R 10 Each independently is: hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group or a hydrazone group; Each is unsubstituted or selected from deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a tetrahydro-2H-pyranyl group, a morpholinyl group, a phenyl group, (C1-C 10 Alkyl)phenyl group, di(C1-C 10 alkyl)phenyl group, biphenyl group, di(phenyl)phenyl group, terphenyl group, naphthyl group, pyridyl group, pyrimidyl group, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ) at least one substituted C1-C 10 Alkyl groups, C2-C 10 Alkenyl groups, C2-C 10 Alkynyl group or C1-C 10 Alkoxy groups; Each is unsubstituted or selected from deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C 10 Alkyl groups, C2-C 10 Alkenyl groups, C2-C 10 Alkynyl group, C1-C 10 an alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a tetrahydro-2H-pyranyl group, a morpholinyl group, a dioxanyl group, a phenyl group, a (C1-C 10 Alkyl)phenyl group, di(C1-C 10 alkyl)phenyl group, biphenyl group, di(phenyl)phenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a benzofuranyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophene ... a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidinyl group, a 2,3-dihydro-1H-indenyl group, a 1,2,3,4-tetrahydronaphthyl group, a 2,3-dihydrobenzodioxinyl group, a benzodioxanyl group, an -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ) is at least one substituted cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, tetrahydro-2H-pyranyl group, morpholinyl group, dioxanyl group, phenyl group, (C1-C 10 Alkyl)phenyl group, di(C1-C 10 alkyl)phenyl group, biphenyl group, di(phenyl)phenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a pyrrolyl group, a thienyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuroyl group, a 1,2,3,4-tetrahydronaphthyl group, a 2,3-dihydrobenzodioxazolyl group, a 1,2,3,4-tetrahydronaphthyl group, a 2,3-dihydrobenzodioxinyl group, or a benzodioxanyl group; or -O(Q1), -S(Q1), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), Among them, Q1 to Q3 and Q 31 To Q 33 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C 10 Alkyl groups, C2-C 10 Alkenyl groups, C2-C 10 Alkynyl group, C1-C 10 an alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a tetrahydro-2H-pyranyl group, a morpholinyl group, a dioxanyl group, a phenyl group, a (C1-C 10 Alkyl)phenyl group, di(C1-C 10 alkyl)phenyl group, biphenyl group, di(phenyl)phenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a benzoyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzo[pi]nyl group, a benzo[pi]nyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzo[pi]nyl group, a benzo[pi]nyl group, a quinol ... A furanyl group, a benzothienyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothienyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a 2,3-dihydro-1H-indenyl group, a 1,2,3,4-tetrahydronaphthyl group, a 2,3-dihydrobenzodioxinyl group or a benzodioxanyl group.
5. The near-infrared light-emitting diode according to claim 1, wherein L1 is selected from the ligand represented by formula 1-1(1): Formula 1-1(1) in, In formula 1-1(1), Ring A1, Ring A2, Z 31 , Z 32 ,X1,X2,R1,R2,b1,b2,R 10a ,* 1 and* 2 each being the same as those defined in claim 1, Ring A 10 is defined as being the same as the ring A1 defined in claim 1, and b10 is defined to be the same as b1 defined in claim 1.
6. The near-infrared light-emitting diode according to claim 1, wherein the organometallic compound containing osmium is selected from Compound 1 to Compound 42: The near-infrared light emitting diode as claimed in claim 1 , wherein the near-infrared light emitting layer further comprises a host. 8 . The near-infrared light emitting diode of claim 1 , wherein the organic layer further comprises a hole transport region between the first electrode and the near-infrared light emitting layer and an electron transport region between the near-infrared light emitting layer and the second electrode. 9 . The near-infrared light emitting diode of claim 8 , wherein at least one selected from the hole transport region, the near-infrared light emitting layer, and the electron transport region comprises a carbazole-containing compound. 10 . The near-infrared light emitting diode of claim 1 , wherein the organic layer further comprises a visible light emitting layer.
11. A device comprising a near-infrared light emitting diode according to any one of claims 1 to 10. 12 . The device of claim 11 , wherein the device further comprises a visible light emitting diode comprising a first electrode, a second electrode, and a visible light emitting layer between the first electrode and the second electrode.
13. The apparatus of claim 11, wherein the apparatus further comprises a sensor configured to identify near infrared light reflected from an object exposed to at least a portion of the near infrared light emitted by the near infrared light emitting diode.
14. The apparatus of claim 13, wherein the object is a part of a human body.
15. The device of claim 11, wherein the device is a transmitting device, an authenticating device, or an electronic device.
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Triode type ionization vacuum gauge and pressure measurement method
KR1020190006434A