Fused cyclic compound and organic light-emitting device comprising same
By using fused cyclic compounds in the emitting layer of the organic light emitting device, challenges in the prior art luminescence efficiency and service life are solved, and the effects of high-efficiency light emission and long-life are achieved.
Patent Information
- Application Number
- CN202510143882.5
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2019-04-09
- Filing Date
- 2020-02-05
- Publication Date
- 2025-05-13
AI Technical Summary
Existing organic light emitting devices have challenges in improving luminescence efficiency and extending service life, especially while maintaining efficient light emission and reducing thermal activation delayed fluorescence.
The fused cyclic compounds represented by Formula 1 are used as the key material in the emission layer. These compounds have high oscillator strength and small ΔEst values, and can cross between the inverted phase systems from triple excited state to singlet excited state through thermal activation, improving luminous efficiency and extending service life.
By using fused cyclic compounds, the efficient light emission, low driving voltage, high efficiency and long service life of the organic light emitting device are achieved, while reducing the service life deterioration caused by triplet concentration.
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Figure CN119978007A_ABST
Abstract
Description
[0001] CROSS-REFERENCE TO RELATED APPLICATIONS
[0002] This application is a divisional application of Chinese Patent Application No. 202010080326.5, claiming the benefit of Korean Patent Application No. 10-2019-0041497 filed with the Korean Intellectual Property Office on April 9, 2019, the entire contents of which are incorporated herein by reference. Technical Field
[0003] One or more aspects of embodiments of the present disclosure relate to a condensed cyclic compound and an organic light-emitting device including the condensed cyclic compound. Background Art
[0004] Organic light-emitting devices are self-emissive devices that can produce full-color images, and also have wide viewing angles, high contrast, short response times, and superior characteristics in terms of brightness, driving voltage, and / or response speed compared to devices in the art.
[0005] In an example, an organic light-emitting device may include a first electrode arranged (e.g., placed) on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially arranged on the first electrode. Holes provided by the first electrode may move toward the emission layer through the hole transport region, and electrons provided by the second electrode may move toward the emission layer through the electron transport region. Carriers (e.g., holes and electrons) may then recombine in the emission layer to generate excitons. These excitons transition from an excited state to a ground state, thereby generating light. Summary of the invention
[0006] Aspects of embodiments of the present disclosure are directed to 1) a condensed cyclic compound and 2) an organic light-emitting device including the condensed cyclic compound.
[0007] Additional aspects will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the presented embodiments.
[0008] Embodiments of the present disclosure provide a fused cyclic compound represented by Formula 1:
[0009] Formula 1
[0010]
[0011] In formula 1,
[0012] Y 1 Can be N or C (R 1 ), Y 2 Can be N or C (R 2 ), Y 3Can be N or C (R 3 ), Y 4 Can be N or C (R 4 ), Y 5 Can be N or C (R 5 ), Y 6 Can be N or C (R 6 ), Y 7 Can be N or C (R 7 ), Y 8 Can be N or C (R 8 ), Y 9 Can be N or C (R 9 ), Y 10 Can be N or C (R 10 ), Y 11 Can be N or C (R 11 ), Y 12 Can be N or C (R 12 ), Y 13 Can be N or C (R 13 ), Y 14 Can be N or C (R 14 ), and Y 15 Can be N or C (R 15 ), wherein Y 1 To Y 15 At least one of them is not N,
[0013] X 1 Can be selected from O, S, N (R 16 )、C(R 16 )(R 17 ) and Si(R 16 )(R 17 ),
[0014] X 2 Can be selected from O, S, N (R 18 )、C(R 18 )(R 19 ) and Si(R 18 )(R 19 ),as well as
[0015] Selected from R 1 To R 15 At least one of may be a group represented by Formula 2:
[0016] Formula 2
[0017]
[0018] In equation 1 and equation 2,
[0019] L 1To L 3 can be independently selected from a single bond, a substituted or unsubstituted C 5 -C 60 Carbocyclic groups and substituted or unsubstituted C 1 -C 60 Heterocyclic groups,
[0020] a1 to a3 can each independently be an integer from 1 to 3,
[0021] X 3 Can be selected from O, S, N (R 22 )、C(R 22 )(R 23 ) and Si(R 22 )(R 23 ),
[0022] A 1 Can be selected from C 5 -C 30 Carbocyclic groups and C 2 -C 30 Heterocyclic groups,
[0023] Ar 1 To Ar 3 can be independently selected from 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 60heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups and substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic groups,
[0024] R 1 To R 23 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 carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ),
[0025] R 16 and R 17, R 18 and R 19 and / or R 22 and R 23 may be optionally linked to form a saturated ring or an unsaturated ring,
[0026] b20 can be an integer from 1 to 3,
[0027] b21 can be an integer from 1 to 6,
[0028] The substituted C 5 -C 60 The carbocyclic group, the substituted C 1 -C 60 Heterocyclic group, the substituted C 1 -C 60 The alkyl group, the substituted C 2 -C 60 The alkenyl group, the substituted C 2 -C 60 Alkynyl group, the substituted C 1 -C 60 Alkoxy groups, the substituted C 3 -C 10 Cycloalkyl groups, the substituted C 1 -C 10 Heterocycloalkyl group, the substituted C 3 -C 10 Cycloalkenyl group, the substituted C 1 -C 10 Heterocycloalkenyl group, the substituted C 6 -C 60 The aryl group, the substituted C 6 -C 60 The aryloxy group, the substituted C 6 -C 60 Arylthio group, the 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:
[0029] 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;
[0030] 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 -C 60 Alkenyl group, C 2 -C 60 Alkynyl groups and C 1 -C 60 Alkoxy groups;
[0031] 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 -C60 Arylthio group, C 1 -C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups;
[0032] 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 )(Q 23 )、-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 60Aryl 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
[0033] -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 ),as well as
[0034] Q 1 To Q 3 , 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 a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.
[0035] Another embodiment of the present disclosure provides an organic light-emitting device including: a first electrode; a second electrode facing the first electrode; an organic layer between the first electrode and the second electrode, the organic layer including an emission layer; and at least one condensed cyclic compound represented by Formula 1. BRIEF DESCRIPTION OF THE DRAWINGS
[0036] These and / or other aspects will become apparent and more readily understood from the following description of the embodiments taken in conjunction with the accompanying drawings, in which:
[0037] Figure 1 is a schematic view of an organic light emitting device according to an embodiment;
[0038] Figure 2 is a schematic view of an organic light emitting device according to another embodiment;
[0039] Figure 3 is a schematic view of an organic light emitting device according to another embodiment; and
[0040] Figure 4 is a schematic view of an organic light emitting device according to another embodiment. DETAILED DESCRIPTION
[0041] Reference will now be made to the embodiment in more detail, the example examples of the embodiment 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 can have different forms and should not be construed as being limited to the description set forth herein. Therefore, by referring to the accompanying drawings, only the embodiment is described below to explain the aspects of the current description. As used herein, the term "and / or" includes any combination and all combinations of one or more than one of the related listed items. Expressions such as "at least one (kind) in ... ", "one (kind) in ... " and "selected from " when before a column of elements, modify the elements of the entire column, without modifying the single element of the column. In addition, when describing embodiments of the present invention, the use of "may" can refer to "one or more than one embodiment of the present invention".
[0042] The fused cyclic compound according to one or more embodiments is represented by Formula 1:
[0043] Formula 1
[0044]
[0045] In formula 1, Y 1 Can be N or C (R 1 ), Y 2 Can be N or C (R 2 ), Y 3Can be N or C (R 3 ), Y 4 Can be N or C (R 4 ), Y 5 Can be N or C (R 5 ), Y 6 Can be N or C (R 6 ), Y 7 Can be N or C (R 7 ), Y 8 Can be N or C (R 8 ), Y 9 Can be N or C (R 9 ), Y 10 Can be N or C (R 10 ), Y 11 Can be N or C (R 11 ), Y 12 Can be N or C (R 12 ), Y 13 Can be N or C (R 13 ), Y 14 Can be N or C (R 14 ), and Y 15 Can be N or C (R 15 ). Select from Y 1 To Y 15 At least one of them is not N.
[0046] In Formula 1, R 1 To R 15 At least one of may be a group represented by Formula 2:
[0047] Formula 2
[0048]
[0049] In one or more than one embodiment, Y 1 It can be C(R 1 ), Y 2 It can be C(R 2 ), Y 3 It can be C(R 3 ), Y 4 It can be C(R 4 ), Y 5 It can be C(R 5 ), Y 6 It can be C(R 6 ), Y 7 It can be C(R 7 ), Y 8 It can be C(R 8 ), Y 9 It can be C(R9 ), Y 10 It can be C(R 10 ), Y 11 It can be C(R 11 ), Y 12 It can be C(R 12 ), Y 13 It can be C(R 13 ), Y 14 It can be C(R 14 ), and Y 15 It can be C(R 15 ).
[0050] In one or more than one embodiment, Y 1 It can be C(R 1 ), Y 2 It can be C(R 2 ), Y 3 It can be C(R 3 ), Y 4 It can be C(R 4 ), Y 5 It can be C(R 5 ), Y 6 It can be C(R 6 ), Y 7 It can be C(R 7 ), Y 8 It can be C(R 8 ), Y 9 It can be C(R 9 ), Y 10 It can be C(R 10 ), Y 11 It can be C(R 11 ), Y 12 It can be C(R 12 ), Y 13 It can be C(R 13 ), Y 14 It can be C(R 14 ), and Y 15 It can be C(R 15 ). In one or more than one embodiment, R 1 and R 3 To R 15 can be hydrogen independently and simultaneously, and R 2 It may be a group represented by Formula 2:
[0051] Formula 2
[0052]
[0053] In formula 1, X1 Can be selected from O, S, N (R 16 )、C(R 16 )(R 17 ) and Si(R 16 )(R 17 ),as well as
[0054] X 2 Can be selected from O, S, N (R 18 )、C(R 18 )(R 19 ) and Si(R 18 )(R 19 ).
[0055] In one or more than one embodiment, the fused cyclic compound may be represented by one selected from Formula 1-1 to Formula 1-21:
[0056]
[0057]
[0058]
[0059]
[0060] In Formula 1-1 to Formula 1-21,
[0061] Selected from R 1 To R 15 At least one of may be a group represented by Formula 2, and
[0062] R 1 To R 19 may each independently be the same as described herein.
[0063] In one or more than one embodiment, in Formula 1-1 to Formula 1-21, R 1 and R 3 To R 15 can be hydrogen independently and simultaneously, and R 2 It may be a group represented by Formula 2:
[0064] Formula 2
[0065]
[0066] In formula 2, L 1 To L 3 can be independently selected from a single bond, a substituted or unsubstituted C 5 -C 60 Carbocyclic groups and substituted or unsubstituted C 1 -C60 Heterocyclic group.
[0067] In one or more than one embodiment, L 1 To L 3 Can be independently selected from:
[0068] a single bond, a cyclobutylene group, a cyclopentylene group, a cyclohexylene group, 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 phenalenylene group, an anthrylene group, a fluoranthenylene group, a phenanthrenylene group, a py ... a phenylene group, a tetraphenylene group, a perylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a quinolylene group, an isoquinolylene group, a benzoquinolylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene 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, and a dibenzosilylene group; and
[0069] 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 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, a heptalenyl group, an indacenyl group, an acenaphthenyl 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 naphthyl group, a pyrenyl group, a peryl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl 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, -Si(Q 31 )(Q32 )(Q 33 )、-N(Q 31 )(Q 32 ) and -B(Q 31 )(Q 32 ) is at least one substituted cyclobutylene group, cyclopentylene group, cyclohexylene group, phenylene group, pentalenylene group, indenylene group, naphthylene group, azulenylene group, heptalenylene group, indacenylene group, acenaphthenylene group, fluorenylene group, spiro-difluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, phenanthrenylene group, py ... The invention also includes but is not limited to: a benzothiophene group, a tetraphenylene group, a perylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a quinolylene group, an isoquinolylene group, a benzoquinolylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a thienylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophene group, a dibenzofuranylene group, a dibenzothiophene group, a benzocarbazolylene group, a dibenzocarbazolylene group, and a dibenzosilylene group.
[0070] In Formula 2, a1 to a3 may each independently be an integer of 1 to 3.
[0071] a1 means L 1 and when a1 is 2 or 3, 2 or 3 L 1 They may be the same or different from each other. a2 represents L 2 and when a2 is 2 or 3, 2 or 3 L 2 They may be the same or different from each other. a3 represents L 3 and when a3 is 2 or 3, 2 or 3 L 3 May be the same as or different from each other.
[0072] In one or more than one embodiment, L 1 To L 3 may be a single bond at the same time, and a1 to a3 may be 1 at the same time.
[0073] In formula 2, X 3 Can be selected from O, S, N (R 22 )、C(R 22 )(R 23 ) and Si(R 22 )(R 23 ).
[0074] In formula 2, A 1 Can be selected from C 5 -C 30 Carbocyclic groups and C 2 -C 30 Heterocyclic group.
[0075] In one or more than one embodiment, A 1 It can be selected from benzene ring, indene ring, naphthalene ring, anthracene ring, fluorene ring, phenanthrene ring, triphenylene ring, pyrene ring, ring, tetracene ring, pyrrole ring, imidazole ring, pyrazole ring, pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, indole ring, isoindole ring, indazole ring, quinoline ring, isoquinoline ring, benzoquinoline ring, naphthridine ring, quinoxaline ring, quinazoline ring, cinnoline ring, carbazole ring, phenanthridine ring, acridine ring, phenanthroline ring, phenazine ring, benzimidazole ring, furan ring, benzofuran ring, thiophene ring, benzothiophene ring, thiazole ring, isothiazole ring, benzothiazole ring, isoxazole ring, oxazole ring, triazole ring, oxadiazole ring, triazine ring, benzoxazole ring, dibenzofuran ring, dibenzothiophene ring, benzocarbazole ring and dibenzocarbazole ring.
[0076] For example, A 1 The ring may be selected from a benzene ring, a naphthalene ring, a pyridine ring, a pyrimidine ring, and a pyrazine ring, but the embodiments of the present disclosure are not limited thereto.
[0077] For example, A 1 It may be a benzene ring, but embodiments of the present disclosure are not limited thereto.
[0078] In formula 1 and formula 2, Ar 1 To Ar 3 can be independently selected from 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 C6 -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.
[0079] In one or more than one embodiment, Ar 1 To Ar 3 Can be independently selected from:
[0080] C 1 -C 20 Alkyl group, C 2 -C 20 Alkenyl group, C 2 -C 20 Alkynyl groups and C 1 -C 20 Alkoxy groups;
[0081] 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 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 phenyl group, a naphthyl group, a pyridyl group, a pyrimidinyl 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 ) at least one substituted C 1 -C 20 Alkyl group, C 2 -C 20 Alkenyl group, C 2 -C 20 Alkynyl groups and C 1 -C 20 Alkoxy groups;
[0082] 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 phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, a phenanthrenyl group, a anthracenyl group, a fluoranthenyl group, a triphenylphenanthrenyl group, a pyrenyl group, a pyrrolyl group, a furanyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl 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 phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzothiazolyl 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 imidazopyridinyl group, and an imidazopyrimidinyl group; and
[0083] 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 2 -C 20 Alkenyl group, C 2 -C 20 Alkynyl group, C 1 -C 20 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 phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl 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 pyrrolyl group, a furanyl group, a thienyl 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 phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazole group, a benzofuranyl group, a benzothiophenyl group, a benzothiazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazine group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidinyl group, a -Si(Q) group, 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 cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, pentalenyl group, indenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenaltenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a pyrrolyl group, a furanyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl 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 phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzothiazolyl 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 imidazopyridinyl group, and an imidazopyrimidinyl group, and
[0084] Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a cyano group, C 1 -C 20 Alkyl group, C 2 -C 20 Alkenyl group, C 2 -C 20 Alkynyl group, C 1 -C 20 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 20 Aryl group, C 1 -C 20 a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.
[0085] In one or more than one embodiment, Ar 1 To Ar 3 Can be independently selected from:
[0086] Methyl group, -CD 3, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, neopentyl group, n-hexyl group, isohexyl group and phenyl group; and
[0087] 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 methyl group, -CD 3 The present invention may be substituted with at least one of an alkyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a neopentyl group, an n-hexyl group, an isohexyl group and a phenyl group.
[0088] Ar 1 To Ar 3 Can be the same or different from each other. In one or more than one embodiment, Ar 1 To Ar 3 can be identical to each other. For example, Ar 1 To Ar 3 All of them may be an isopropyl group, a phenyl group, a 2,4-dimethylphenyl group or a 2,4,6-trimethylphenyl group.
[0089] In equations 1 and 2, R 1 To R 23 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 carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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 60Aryl 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)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ),
[0090] R 16 and R 17 , R 18 and R 19 and / or R 22 and R 23 may be optionally linked to form a saturated ring or an unsaturated ring,
[0091] b20 may be an integer from 1 to 3, and
[0092] b21 can be an integer from 1 to 6.
[0093] In one or more than one embodiment, R 1 To R 23 Can be independently selected from:
[0094] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, methyl group, -CD 3 , ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, neopentyl group, n-hexyl group, isohexyl group and phenyl group; and
[0095] 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 methyl group, -CD 3The present invention may be substituted with at least one of an alkyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a neopentyl group, an n-hexyl group, an isohexyl group and a phenyl group.
[0096] In one or more than one embodiment, X 1 Can be selected from O, S, N (R 16 )、C(R 16 )(R 17 ) and Si(R 16 )(R 17 ), X 2 Can be selected from O, S, N (R 18 )、C(R 18 )(R 19 ) and Si(R 18 )(R 19 ), and X 3 Can be selected from O, S, N (R 22 )、C(R 22 )(R 23 ) and Si(R 22 )(R 23 ), R 16 To R 19 , R 22 and R 23 Can be independently selected from:
[0097] Methyl group, -CD 3 , ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, neopentyl group, n-hexyl group, isohexyl group and phenyl group; and
[0098] 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 methyl group, -CD 3 The present invention may be substituted with at least one of an alkyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a neopentyl group, an n-hexyl group, an isohexyl group and a phenyl group.
[0099] In one or more than one embodiment, X 1 It can be C(R 16 )(R 17 ), R 16 and R 17may each independently be a phenyl group, and R 16 and R 17 can be connected via a single bond, i.e., comprising C(R 16 )(R 17 ) can be represented by a fluorene ring.
[0100] In one or more than one embodiment, X 2 It can be C(R 18 )(R 19 ), R 18 and R 19 may each independently be a phenyl group, and R 18 and R 19 can be connected via a single bond, i.e., comprising C(R 18 )(R 19 ) can be represented by a fluorene ring.
[0101] In one or more than one embodiment, in Formula 1, selected from R 1 To R 15 At least one of may be a group represented by Formula 2A.
[0102] Formula 2A
[0103]
[0104] In Formula 2A,
[0105] X 3 , L 1 To L 3 、a1 to a3、Ar 3 , R 20 , R 21 , b20 and b21 may each independently be the same as described herein, and
[0106] * indicates the connection site with the adjacent atom.
[0107] In one or more than one embodiment, in Formula 1, selected from R 1 To R 15 At least one of may be a group represented by Formula 2A-1:
[0108] Formula 2A-1
[0109]
[0110] In Formula 2A-1,
[0111] X 3 ,Ar 3 , R 20 , R 21, b20 and b21 may each independently be the same as described herein, and
[0112] * indicates the connection site with the adjacent atom.
[0113] In one or more than one embodiment, in Formula 1, selected from R 1 To R 15 At least one of the groups may be selected from the group represented by Formula 2A-2 to Formula 2A-8:
[0114]
[0115] In Formula 2A-2 to Formula 2A-8,
[0116] Ar 3 can be the same as described herein, and
[0117] * indicates the connection site with the adjacent atom.
[0118] In one or more than one embodiment, the fused cyclic compound can be selected from Compound 1 to Compound 117:
[0119]
[0120]
[0121]
[0122]
[0123]
[0124]
[0125]
[0126]
[0127]
[0128]
[0129]
[0130]
[0131]
[0132] Since the fused cyclic compound according to one or more embodiments includes the fused cyclic structure represented by Formula 1, the fused cyclic compound may have high oscillator strength due to multiple resonance and may have a small ΔE since the singlet energy level and triplet energy level of the molecule do not overlap with each other. st In this regard, even at room temperature, antiphase intersystem crossing from a triplet excited state to a singlet excited state by thermal activation may be possible. Therefore, the fused cyclic compound represented by Formula 1 may exhibit delayed fluorescence. Since the excitons in the triplet state are used for light emission, the luminous efficiency may be improved.
[0133] For example, in the structure represented by Formula 1, since X 1 and X 2 is represented by an atom with electron donating properties, and since X 1 and X 2 The benzene part is located in a para position relative to the boron atom (the benzene part is located between the boron atom and X 1 and X 2 The possibility of having a charge transfer characteristic in a higher-order triplet phase higher than T1 or higher can be increased, thereby having a small E st .
[0134] In addition, in the structure represented by Formula 1, 1 and X 2 The fused ring The angle of bonding with the adjacent 1,4-azahydrocarbyl boron is reduced to suppress the decrease of the T1 energy of the fused cyclic compound. Therefore, the E of the fused cyclic compound according to one or more embodiments can be reduced. st For example, in formula 1-1 (when X 1 N(R 16 ) and X 2 N(R 18 )) contains X 1 or X 2 The fused ring has an amine (*-N(Ar 1 )-*' or *-N(Ar 2 )-*') is substituted at the 4-position of each carbazole ring. In this example, as shown below, since *-N(Ar 1 )-*' or *-N(Ar 2 )-*' relative to the partial structure of the biphenyl group connected to the ortho position, so the reduction of T1 energy can be reduced. Therefore, the fused cyclic compound according to one or more embodiments can have a relatively small ΔE st .
[0135] Formula 1-1
[0136]
[0137] In addition, since the fused cyclic compound represented by Formula 1 has a bulky structure, the distance between dopant molecules can be increased, thereby reducing dexter energy transfer. Therefore, the service life deterioration caused by the increase of triplet concentration, for example, the service life deterioration caused by triplet-triplet annihilation (TTA) and / or triplet-polaron quenching (TPQ) can be reduced.
[0138] For example, the fused cyclic compound represented by Formula 1 may satisfy Equation 1:
[0139] Equation 1
[0140] △E st =S1–T1≤0.4eV.
[0141] In Equation 1, S1 is the singlet energy level of the fused cyclic compound, and
[0142] T1 is the triplet energy level of the fused cyclic compound.
[0143] In addition, the fused cyclic compound may include a group represented by Formula 2 in the molecular structure. In the group represented by Formula 2, a carbon atom at a specific position of the benzene part (“C 4 ”) can be linked to the nitrogen atom of the amine group. For example, when X 3 When the fused ring is carbazole, the 4-position of carbazole can be connected to a nitrogen atom or an amine group. Due to such structural characteristics, the carbon atom at another position (e.g., "C 1 ”, “C 2 ” and / or “C 3 Compared with the amine-containing compound in which the condensed cyclic compound is connected to the carbon (carbon) and nitrogen atoms, the condensed cyclic compound may have a relatively high triplet energy. From the same point of view, it can be understood that as the connection structure changes in the order of para, meta and ortho positions, a trend of increasing triplet energy is observed in the biphenyl structure. According to one or more embodiments, since the condensed cyclic compound may have a relatively small ΔE st , thus the thermally activated delayed fluorescence properties can be improved.
[0144] The fused cyclic group including the group represented by Formula 2 has a relatively high probability of being positioned in a perpendicular bending direction relative to the plane including the core structure. This can lead to steric hindrance to the molecule, thereby preventing or reducing the approach to adjacent molecules and reducing dexter energy transfer. Therefore, as described above, the deterioration of the service life caused by the increase in triplet concentration can be reduced.
[0145]
[0146] In addition, since the condensed cyclic compound represented by Formula 1 has a relatively high charge (hole or electron) transport capability, it is possible to improve the exciton formation ratio in the emission layer of the organic light-emitting device including the condensed cyclic compound represented by Formula 1. Therefore, the organic light-emitting device can have a low driving voltage, high efficiency, a long service life, and a high maximum quantum efficiency.
[0147] The synthesis method for the fused cyclic compound represented by Formula 1 should be apparent to one of ordinary skill in the art by referring to the following examples.
[0148] The fused cyclic compound represented by Formula 1 can be used between a pair of electrodes of an organic light-emitting device. For example, the fused cyclic compound represented by Formula 1 can be included in at least one selected from a hole transport region, an electron transport region, and an emission layer. In one or more embodiments, the fused cyclic compound represented by Formula 1 can be used as a material for a covering layer located outside a pair of electrodes of an organic light-emitting device.
[0149] One or more embodiments of the present disclosure provide an organic light-emitting device including: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, the organic layer including an emission layer and at least one condensed cyclic compound represented by Formula 1.
[0150] In one or more embodiments, the first electrode may be an anode,
[0151] The second electrode may be a cathode,
[0152] The organic layer may comprise a fused cyclic compound,
[0153] The organic layer may further include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode,
[0154] The hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof, and
[0155] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0156] In one or more embodiments, the emission layer of the organic light-emitting device may include at least one fused cyclic compound. The fused cyclic compound included in the emission layer may serve as a thermally activated delayed fluorescence (TADF) emitter, so that the emission layer may emit delayed fluorescence.
[0157] In one or more embodiments, the emission layer of the organic light-emitting device may include at least one fused cyclic compound and may further include a host. Here, the host may include at least one selected from anthracene-based compound, pyrene-based compound, spiro-bifluorene-based compound, carbazole-based compound, benzimidazole-based compound, and phosphine oxide-based compound. The amount of the host included in the emission layer may be greater than the amount of the fused cyclic compound included in the emission layer. For example, based on 100 parts by weight of the emission layer, the amount of the host may be from about 0.1 parts by weight to about 30 parts by weight.
[0158] In one or more embodiments, the emission layer of the organic light-emitting device may include the condensed cyclic compound, and may emit blue light having a maximum emission wavelength of 420 nm to 480 nm both inclusive.
[0159] In one or more embodiments, the hole transport region of the organic light-emitting device may include a hole transport layer, and the hole transport layer may include a first hole transport layer and a second hole transport layer.
[0160] The term "organic layer" as used herein may refer to a single layer and / or a plurality of layers disposed (positioned) between a first electrode and a second electrode of an organic light-emitting device. Materials included in the "organic layer" are not limited to organic materials.
[0161] Figure 1 Description
[0162] Figure 1 is a schematic cross-sectional view of an organic light-emitting device 10 according to an embodiment. The organic light-emitting device 10 includes a first electrode 110 , an organic layer 150 , and a second electrode 190 .
[0163] In the following, we will discuss Figure 1 A structure of an organic light-emitting device 10 and a method of manufacturing the organic light-emitting device 10 according to the embodiment are described.
[0164] First electrode 110
[0165] exist Figure 1 In the embodiment, the substrate may be additionally arranged under the first electrode 110 or over the second electrode 190. The substrate may be a glass substrate or a plastic substrate each having excellent (or suitable) mechanical strength, thermal stability, transparency, surface smoothness, ease of handling and / or water resistance.
[0166] The first electrode 110 may be formed by depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 may be selected from materials having a high work function to facilitate hole injection.
[0167] 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 embodiments of the present disclosure are not limited thereto. In one or more than one embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the material used to form the first electrode 110 may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof, but the embodiments of the present disclosure are not limited thereto.
[0168] The first electrode 110 may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 110 is not limited thereto.
[0169] Organic layer 150
[0170] The organic layer 150 may be disposed on the first electrode 110. The organic layer 150 may include an emission layer.
[0171] The organic layer 150 may further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 190 .
[0172] Hole transport region in the organic layer 150
[0173] The hole transport region may have i) a single-layer structure including a single layer containing a single material, ii) a single-layer structure including 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.
[0174] The hole transport region may include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an emission assisting layer, and an electron blocking layer.
[0175] For example, the hole transport zone may have a single-layer structure including a single layer containing a plurality of different materials, or a multi-layer structure having a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission auxiliary layer structure, a hole injection layer / emission auxiliary layer structure, a hole transport layer / emission auxiliary layer structure, or a hole injection layer / hole transport layer / emission auxiliary layer structure, wherein for each structure, the constituent layers are stacked in sequence from the first electrode 110 in this prescribed order, but the structure of the hole transport zone is not limited thereto.
[0176] 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:
[0177]
[0178] Formula 201
[0179]
[0180] Formula 202
[0181]
[0182] In equation 201 and equation 202,
[0183] 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,
[0184] L 205 Can be selected from *-O-*', *-S-*', *-N(Q 201 )-*', substituted or unsubstituted C 1 -C 20 Alkylene group, substituted or unsubstituted C 2 -C 20 Alkenylene group, substituted or unsubstituted C3 -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,
[0185] xa1 to xa4 can each independently be an integer from 0 to 3,
[0186] xa5 can be an integer from 1 to 10, and
[0187] 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.
[0188] For example, in Equation 202, R 201 and R 202 can be optionally linked via a single bond, a dimethyl-methylene group or a diphenyl-methylene group, and R 203 and R 204 The attachment may optionally be via a single bond, a dimethyl-methylene group or a diphenyl-methylene group.
[0189] In one or more than one embodiments, in Formula 201 and Formula 202,
[0190] L 201 To L 205 Can be independently selected from:
[0191] 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 phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a phenylene group, a phenanthrenylene group, a py ... 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
[0192] 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(Q31 )(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, acenaphthenylene group, fluorenylene group, spiro-difluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenalenylene 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 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
[0193] 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.
[0194] In one or more than one embodiments, xa1 to xa4 can each independently be 0, 1 or 2.
[0195] In one or more than one embodiments, xa5 can be 1, 2, 3 or 4.
[0196] In one or more than one embodiment, R 201 To R 204 and Q 201 Can be independently selected from:
[0197] a phenyl group, a biphenyl group, a terphenyl group, 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 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
[0198] 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, and
[0199] Q 31 To Q 33 Same as described above.
[0200] In one or more than one embodiment, in Formula 201, R 201 To R 203 At least one of can be independently selected from:
[0201] fluorenyl groups, spiro-bifluorenyl groups, carbazolyl groups, dibenzofuranyl groups, and dibenzothiophenyl groups; and
[0202] 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 a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,
[0203] However, the embodiments of the present disclosure are not limited thereto.
[0204] In one or more than one embodiment, in Formula 202, i) R 201 and R 202 can be connected via a single bond, and / or ii) R 203 and R 204 Can connect via one-touch.
[0205] In one or more than one embodiment, R selected from Formula 202 201 To R 204 At least one of may be selected from:
[0206] a carbazolyl group; and
[0207] 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 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 dibenzothienyl group,
[0208] However, the embodiments of the present disclosure are not limited thereto.
[0209] The compound represented by Formula 201 can be represented by the following Formula 201-1:
[0210] Formula 201-1
[0211]
[0212] For example, the compound represented by Formula 201 may be represented by the following Formula 201-2, but embodiments of the present disclosure are not limited thereto:
[0213] Formula 201-2
[0214]
[0215] In one or more than one embodiments, the compound represented by Formula 201 may be represented by the following Formula 201-2(1), but the embodiments of the present disclosure are not limited thereto:
[0216] Formula 201-2(1)
[0217]
[0218] In one or more than one embodiments, the compound represented by Formula 201 can be represented by the following Formula 201A:
[0219] Formula 201A
[0220]
[0221] In one or more than one embodiments, the compound represented by Formula 201 may be represented by the following Formula 201A(1), but the embodiments of the present disclosure are not limited thereto:
[0222] Formula 201A(1)
[0223]
[0224] In one or more than one embodiments, the compound represented by Formula 201 may be represented by the following Formula 201A-1, but the embodiments of the present disclosure are not limited thereto:
[0225] Formula 201A-1
[0226]
[0227] In one or more than one embodiments, the compound represented by Formula 202 can be represented by the following Formula 202-1:
[0228] Formula 202-1
[0229]
[0230] In one or more than one embodiments, the compound represented by Formula 202 can be represented by the following Formula 202-1(1):
[0231] Formula 202-1(1)
[0232]
[0233] In one or more than one embodiments, the compound represented by Formula 202 can be represented by the following Formula 202A:
[0234] Formula 202A
[0235]
[0236] In one or more than one embodiments, the compound represented by Formula 202 can be represented by the following Formula 202A-1:
[0237] Formula 202A-1
[0238]
[0239] In equation 201-1, equation 201-2, equation 201-2(1), equation 201A, equation 201A(1), equation 201A-1, equation 202-1, equation 202-1(1), equation 202A, and equation 202A-1,
[0240] L 201 To L 203, xa1 to xa3, xa5 and R 202 To R 204 Same as described above,
[0241] L 205 may be selected from phenylene groups and fluorenylene groups,
[0242] X 211 Can be selected from O, S and N (R 211 ),
[0243] X 212 Can be selected from O, S and N (R 212 ),
[0244] R 211 and R 212 can be independently compared with R 203 The same definitions, and
[0245] 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.
[0246] The hole transport region may include at least one compound selected from Compound HT1 to Compound HT48, but embodiments of the present disclosure are not limited thereto:
[0247]
[0248]
[0249]
[0250]
[0251] The thickness of the hole transport region may be about to about For example, 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 For example, about to about and the thickness of the hole transport layer may be about to about For example, about to about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within any of these ranges, satisfactory (or suitable) hole transport characteristics may be obtained without a significant increase in driving voltage.
[0252] The emission assisting layer can increase light emission efficiency by compensating the optical resonance distance according to the wavelength of light emitted by the emission layer, and the electron blocking layer can block or reduce the flow of electrons from the electron transport region. The emission assisting layer and the electron blocking layer can each independently include any one of the materials described above.
[0253] p-dopant
[0254] In addition to the materials described above, the hole transport region may further include a charge generating material for improving the conductive property. The charge generating material may be dispersed uniformly or non-uniformly in the hole transport region.
[0255] The charge generating material may be, for example, a p-dopant.
[0256] In one or more embodiments, the p-dopant can have a lowest unoccupied molecular orbital (LUMO) energy level of -3.5 eV or less.
[0257] 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 embodiments of the present disclosure are not limited thereto.
[0258] In one or more than one embodiments, the p-dopant may include at least one selected from the group consisting of:
[0259] Quinone derivatives, for example tetracyanoquinodimethane (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);
[0260] Metal oxides, such as tungsten oxide and / or molybdenum oxide;
[0261] 1,4,5,8,9,12-Hexaazatriphenylene-hexacarbonitrile (HAT-CN); and
[0262] The compound represented by formula 221,
[0263] However, the embodiments of the present disclosure are not limited thereto:
[0264]
[0265] Formula 221
[0266]
[0267] In formula 221,
[0268] 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 may have a cyano group, -F, -Cl, -Br, -I, C substituted by -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.
[0269] Emission layer in the organic layer 150
[0270] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer can be patterned into a red emission layer, a green emission layer, or a blue emission layer according to the sub-pixel. In one or more embodiments, the emission layer may have a stacked structure of two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer, wherein the two or more layers are in contact with each other or spaced apart from each other. In one or more embodiments, the emission layer may include two or more materials selected from a red light-emitting material, a green light-emitting material, and a blue light-emitting material, wherein the two or more materials are mixed with each other in a single layer to emit white light.
[0271] The emission layer may include a host and a dopant. The dopant may include at least one selected from a phosphorescent dopant and a fluorescent dopant.
[0272] In the emission layer, the amount of the dopant may be about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but embodiments of the present disclosure are not limited thereto.
[0273] The thickness of the emission layer can be about to about For example, about to about When the thickness of the emission layer is within this range, excellent (or suitable) light emission characteristics may be obtained without a significant increase in driving voltage.
[0274] Subject in the emission layer
[0275] In one or more than one embodiment, the host may comprise a compound represented by the following formula 301:
[0276] Formula 301
[0277] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 .
[0278] In formula 301,
[0279] Ar 301 It can be substituted or unsubstituted C 5 -C 60 A carbocyclic group or a substituted or unsubstituted C 1 -C 60 Heterocyclic groups,
[0280] xb11 can be 1, 2 or 3,
[0281] 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 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,
[0282] xb1 can be an integer from 0 to 5.
[0283] 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 60heteroaryl 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 ),
[0284] xb21 can be an integer from 1 to 5, and
[0285] 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 embodiments of the present disclosure are not limited thereto.
[0286] In one or more than one embodiment, Ar in Formula 301 301 Can be selected from:
[0287] 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
[0288] 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, groups, naphthacene groups, phenanthracene groups, perylene groups, pentaphenyl groups, indenoanthracene groups, dibenzofuran groups and dibenzothiophene groups, and
[0289] 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, but the embodiments of the present disclosure are not limited thereto.
[0290] When xb11 in formula 301 is two or more, two or more Ar 301 Can connect via one-touch.
[0291] In one or more than one embodiments, the compound represented by Formula 301 can be represented by the following Formula 301-1 or Formula 301-2:
[0292] Formula 301-1
[0293]
[0294] Formula 301-2
[0295]
[0296] In Formula 301-1 to Formula 301-2,
[0297] Ring A 301 To Ring A 304 can be independently selected from a benzene ring, a naphthalene ring, a phenanthrene ring, a fluoranthene ring, a triphenylene ring, a pyrene ring, ring, a pyridine ring, a pyrimidine ring, an indene ring, a fluorene ring, a spiro-bifluorene ring, a benzofluorene ring, a dibenzofluorene ring, an indole ring, a carbazole ring, a benzocarbazole ring, a dibenzocarbazole ring, a furan ring, a benzofuran ring, a dibenzofuran ring, a naphthofuran ring, a benzonaphthofuran ring, a dinaphthofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a naphthothiophene ring, a benzonaphthothiophene ring and a dinaphthothiophene ring,
[0298] X 301 Can be O, S or N-[(L 304) xb4 -R 304 ],
[0299] 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 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),
[0300] xb22 and xb23 can each independently be 0, 1 or 2,
[0301] L 301 、xb1、R 301 and Q 31 To Q 33 It can be understood by referring to the corresponding description presented herein,
[0302] L 302 To L 304 can be independently related to L 301 The same as defined,
[0303] xb2 to xb4 may each independently be the same as defined with respect to xb1, and
[0304] R 302 To R 304 can be independently compared with R 301 The same as defined.
[0305] For example, L in Formula 301, Formula 301-1, and Formula 301-2 301 To L 304 Can be independently selected from:
[0306] 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
[0307] 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 )(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, and
[0308] Q 31 To Q 33 Same as described above.
[0309] In one or more than one embodiments, R in Formula 301, Formula 301-1, and Formula 301-2 301 To R 304 Can be independently selected from:
[0310] 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
[0311] 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 )(Q 33 )、-N(Q31 )(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 pyrazinyl group, 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, and
[0312] Q 31 To Q 33 Same as described above.
[0313] In one or more embodiments, the host can include an alkaline earth metal complex. For example, the host can be selected from a Be complex (eg, compound H55), a Mg complex, and a Zn complex.
[0314] 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(carbazolyl-9-yl)benzene (TCP), and compounds H1 to H55, but embodiments of the present disclosure are not limited thereto:
[0315]
[0316]
[0317]
[0318] The phosphorescent dopant contained in the emission layer in the organic layer 150
[0319] The phosphorescent dopant may include an organic metal complex represented by the following Formula 401:
[0320] Formula 401
[0321] M(L 401 ) xc1 (L 402 ) xc2
[0322] Formula 402
[0323]
[0324] In equations 401 and 402,
[0325] M may be selected from iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh) and thulium (Tm),
[0326] L 401 A ligand represented by the formula 402 may be selected, and xc1 may be 1, 2 or 3, wherein when xc1 is two or more than two, two or more L 401 can be the same or different from each other,
[0327] L 402 It can be an organic ligand, and xc2 can be an integer from 0 to 4, wherein when xc2 is two or more than two, two or more L 402 Can be the same or different from each other
[0328] X 401 To X 404 may each independently be nitrogen or carbon,
[0329] X 401 and X 403 can be connected via single or double bonds, and X 402 and X 404 Can be connected via single or double bonds,
[0330] A 401 and A 402 Can be independently selected from C 5-C 60 Carbocyclic groups and C 1 -C 60 Heterocyclic groups,
[0331] X 405 It can be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 411 )-*'、*-C(Q 411 )(Q 412 )-*'、*-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 )=*'or*=C=*', where Q 411 and Q 412 can be independently hydrogen, deuterium, C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group,
[0332] X 406 Can be a single bond, O or S,
[0333] R 401 and R 402 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 substituted or unsubstituted C 1 -C 20 Alkyl groups, substituted or unsubstituted C 1 -C 20 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 60heteroaryl group, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O) 2 (Q 401 ) and -P(=O)(Q 401 )(Q 402 ), where Q 401 To Q 403 Can be independently selected from C 1 -C 10 Alkyl group, C 1 -C 10 Alkoxy groups, C 6 -C 20 Aryl groups and C 1 -C 20 Heteroaryl groups,
[0334] xc11 and xc12 may each independently be an integer from 0 to 10, and
[0335] * and *' in Formula 402 each represent a bonding site to M in Formula 401.
[0336] In one or more than one embodiments, A in Formula 402 401 and A 402 Each of the phenyl groups may be independently selected from a phenyl group, a naphthalene group, a fluorene group, a spiro-bifluorene group, an indene group, a pyrrole group, a thiophene group, a furan 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, a quinoline group, an isoquinoline group, a benzoquinoline group, a quinoxaline group, a quinazoline group, a carbazole group, a benzimidazole group, a benzofuran group, a benzothiophene group, an isobenzothiophene group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a dibenzofuran group, and a dibenzothiophene group.
[0337] In one or more than one embodiment, in Formula 402, i) X 401 may be nitrogen, and X 402 It can be carbon, or ii) X 401 and X 402 They may each be nitrogen at the same time.
[0338] In one or more than one embodiments, R in Formula 402 401 and R 402 Can be independently selected from:
[0339] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C 1 -C 20 Alkyl groups and C 1 -C 20 Alkoxy groups;
[0340] each of which is substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a phenyl group, a naphthyl group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, and a norbornenyl group; 1 -C 20 Alkyl groups and C 1 -C 20 Alkoxy groups;
[0341] a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;
[0342] 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 20a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group substituted with at least one of an alkoxy group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and
[0343] -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O) 2 (Q 401 ) and -P(=O)(Q 401 )(Q 402 ),as well as
[0344] Q 401 To Q 403 Can be independently selected from C 1 -C 10 Alkyl group, C 1 -C 10 An alkoxy group, a phenyl group, a biphenyl group, and a naphthyl group, but the embodiments of the present disclosure are not limited thereto.
[0345] In one or more embodiments, when xc1 in Formula 401 is two or greater than two, two or more L 401 Two A's 401 Optionally, X may be linked to 407 Connect, or two or more L 401 Two A's 402 Optionally, X may be linked to 408 Connection (see, for example, Compound PD1 to Compound PD4 and Compound PD7). 407 and X 408can be each independently a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 413 )-*'、*-C(Q 413 )(Q 414 )-*' or *-C(Q 413 )=C(Q 414 )-*'(where Q 413 and Q 414 can be independently hydrogen, deuterium, C 1 -C 20 Alkyl group, C 1 -C 20 An alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group), but the embodiments of the present disclosure are not limited thereto.
[0346] L in Formula 401 402 It can be a monovalent organic ligand, a divalent organic ligand or a trivalent organic ligand. 402 It may be a halogen, a diketone (e.g., acetylacetonate), a carboxylic acid (e.g., picolinate), -C(=O), an isonitrile, -CN, and a phosphide (e.g., phosphine and / or phosphite), but the embodiments of the present disclosure are not limited thereto.
[0347] In one or more than one embodiments, the phosphorescent dopant may be selected from, for example, Compound PD1 to Compound PD25, but the embodiments of the present disclosure are not limited thereto:
[0348]
[0349] Fluorescent dopants in the emitting layer
[0350] The fluorescent dopant may include a condensed cyclic compound represented by Formula 1, which may serve as a TADF emitter.
[0351] The fluorescent dopant may further include an arylamine compound and / or a styrylamine compound.
[0352] The fluorescent dopant may include a compound represented by the following Formula 501:
[0353] Formula 501
[0354]
[0355] In formula 501,
[0356] Ar 501 It can be substituted or unsubstituted C 5 -C 60 A carbocyclic group or a substituted or unsubstituted C 1-C 60 Heterocyclic groups,
[0357] L 501 To L 503 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,
[0358] xd1 to xd3 may each independently be an integer from 0 to 3,
[0359] R 501 and R 502 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 fused polycyclic group, and a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, and
[0360] xd4 can be an integer from 1 to 6.
[0361] In one or more than one embodiment, Ar in Formula 501 501 Can be selected from:
[0362] naphthyl group, heptalene 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, and an indenophenanthrene group; and
[0363] 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 a naphthyl group substituted with at least one of an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group, a heptalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, group, a naphthacene group, a phenanthrene group, a perylene group, a pentaphenyl group, an indenoanthracene group and an indenophenanthrene group.
[0364] In one or more than one embodiments, L in Formula 501 501 To L 503 Can be independently selected from:
[0365] 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 benzothienylene group, a dibenzofuranylene group, a dibenzothienylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilylene group, and a pyridylene group; and
[0366] 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, The invention also includes at least one substituted phenylene group, naphthyl group, fluorenyl group, spiro-difluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, anthracen ... The invention also includes but is not limited to: 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 benzothienylene group, a dibenzofuranylene group, a dibenzothienylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilylene group, and a pyridylene group.
[0367] In one or more than one embodiment, R in Formula 501 501 and R 502 Can be independently selected from:
[0368] 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 benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilyl group, and a pyridyl group; and
[0369] 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 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, and -Si(Q) 31 )(Q 32 )(Q 33 ) 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 benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilyl group, and a pyridyl group, and
[0370] 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.
[0371] In one or more than one embodiments, xd4 in Formula 501 may be 2, but embodiments of the present disclosure are not limited thereto.
[0372] For example, the fluorescent dopant may be selected from Compound FD1 to Compound FD22:
[0373]
[0374]
[0375]
[0376] In one or more than one embodiments, the fluorescent dopant may be selected from the following compounds, but the embodiments of the present disclosure are not limited thereto:
[0377]
[0378] Electron transport region in the organic layer 150
[0379] The electron transport region may have i) a single-layer structure including a single layer including a single material, ii) a single-layer structure including a single layer including a plurality of different materials, or iii) a multi-layer structure including a plurality of layers including a plurality of different materials.
[0380] 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 embodiments of the present disclosure are not limited thereto.
[0381] For example, 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 for each structure, the constituent layers are stacked sequentially from the emission layer. However, the embodiment of the structure of the electron transport region is not limited thereto.
[0382] The electron transport region (eg, a buffer layer, a hole blocking layer, an electron control layer, and / or an electron transport layer in the electron transport region) may include a metal-free compound containing at least one π-electron-depleted nitrogen-containing ring.
[0383] A "π-electron-depleted nitrogen-containing ring" may refer to a C-containing ring having at least one *-N=*' moiety as a ring-forming part. 1 -C 60 Heterocyclic group.
[0384] 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 two or more 5- to 7-membered heteromonocyclic groups, each having at least one *-N=*' moiety, are fused to each other, 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 carbocyclic group is a fused heteropolycyclic group.
[0385] Examples of π-electron-depleted nitrogen-containing rings include, but are not limited to, 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.
[0386] For example, the electron transport region may include a compound represented by the following Formula 601:
[0387] Formula 601
[0388] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .
[0389] In formula 601,
[0390] Ar 601 It can be substituted or unsubstituted C 5 -C 60 A carbocyclic group or a substituted or unsubstituted C 1 -C 60 Heterocyclic groups,
[0391] xe11 can be 1, 2 or 3,
[0392] 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,
[0393] xe1 can be an integer from 0 to 5,
[0394] 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)(Q 601 )、-S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ),
[0395] 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
[0396] xe21 can be an integer from 1 to 5.
[0397] In one or more than one 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.
[0398] In one or more than one embodiment, Ar in Formula 601 601 Can be selected from:
[0399] 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
[0400] 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 )、-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, and
[0401] 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.
[0402] When xe11 in formula 601 is 2 or greater, two or more Ar 601 Can connect via one-touch.
[0403] In one or more than one embodiment, Ar in Formula 601 601 It may be an anthracene group.
[0404] In one or more than one embodiments, the compound represented by Formula 601 can be represented by the following Formula 601-1:
[0405] Formula 601-1
[0406]
[0407] In formula 601-1,
[0408] X 614 Can be N or C (R 614 ), X 615 Can be N or C (R 615 ), and X 616 Can be N or C (R 616 ), where X 614 To X 616 At least one of may be N,
[0409] L 611 To L 613 can be independently related to L 601 The same definition,
[0410] xe611 to xe613 can each independently be the same as defined for xe1,
[0411] R 611 To R 613 can be independently compared with R 601 The same definitions, and
[0412] 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.
[0413] In one or more than one embodiments, L in Formula 601 and Formula 601-1 601 and L 611 To L 613 Can be independently selected from:
[0414] 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
[0415] 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, 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,
[0416] However, the embodiments of the present disclosure are not limited thereto.
[0417] In one or more than one embodiments, xe1 and xe611 to xe613 in Formula 601 and Formula 601-1 can each independently be 0, 1 or 2.
[0418] In one or more than one embodiments, R in Formula 601 and Formula 601-1 601 and R 611 To R 613 Can be independently selected from:
[0419] 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;
[0420] 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
[0421] -S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ),as well as
[0422] Q 601 and Q 602 Same as described above.
[0423] The electron transport region may include at least one compound selected from Compound ET1 to Compound ET36, but embodiments of the present disclosure are not limited thereto:
[0424]
[0425]
[0426]
[0427]
[0428] In one or more than one embodiment, the electron transport region may include a 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:
[0429]
[0430] The thickness of the buffer layer, the hole blocking layer and / or the electron control layer may each independently be about to about For example, about to about When the thickness of the buffer layer, the hole blocking layer and / or the electron control layer is within any of these ranges, the electron transport region may have excellent (or suitable) hole blocking characteristics and / or electron control characteristics without a significant increase in driving voltage.
[0431] The thickness of the electron transport layer can be about to about For example, about to about When the thickness of the electron transport layer is within the above-described range, satisfactory (or suitable) electron transport characteristics may be obtained without a significant increase in driving voltage.
[0432] The electron transport region (eg, an electron transport layer in the electron transport region) may further include a metal-containing material in addition to the materials described above.
[0433] The metal-containing material may include at least one selected from an alkali metal complex and an alkaline earth metal complex. The alkali metal complex may include a metal ion selected from Li ions, Na ions, K ions, Rb ions and Cs ions, and the alkaline earth metal complex may include a metal ion selected from Be ions, Mg ions, Ca ions, Sr ions and Ba ions. The ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline and cyclopentadiene, but the embodiments of the present disclosure are not limited thereto.
[0434] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, compounds ET-D1 (lithium hydroxyquinoline, LiQ) and / or ET-D2:
[0435]
[0436] The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 190. The electron injection layer may directly contact the second electrode 190.
[0437] The electron injection layer may have i) a single-layer structure including a single layer including a single material, ii) a single-layer structure including a single layer including a plurality of different materials, or iii) a multi-layer structure including a plurality of layers including a plurality of different materials.
[0438] 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 any combination thereof.
[0439] The alkali metal may be selected from Li, Na, K, Rb, and Cs. In one or more embodiments, the alkali metal may be Li, Na, or Cs. In one or more embodiments, the alkali metal may be Li or Cs, but the embodiments of the present disclosure are not limited thereto.
[0440] The alkaline earth metal may be selected from Mg, Ca, Sr and Ba.
[0441] The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb and Gd.
[0442] The alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound may each independently be selected from oxides and halides (eg, fluorides, chlorides, bromides, and / or iodides) of alkali metals, alkaline earth metals, and rare earth metals, respectively.
[0443] The alkali metal compound may be selected from alkali metal oxides (e.g., Li 2 O, Cs 2 O and / or K 2 O) and alkali metal halides (e.g., LiF, NaF, CsF, KF, LiI, NaI, CsI and / or KI). In one or more embodiments, the alkali metal compound may be selected from LiF, Li 2 O, NaF, LiI, NaI, CsI and KI, but the embodiments of the present disclosure are not limited thereto.
[0444] The alkaline earth metal compound may be selected from alkaline earth metal oxides, such as BaO, SrO, CaO, Ba x Sr 1-x O(0 < x < 1) and / or Ba x Ca 1-x O(0 < x < 1). In one or more embodiments, the alkaline earth metal compound may be selected from BaO, SrO and CaO, but the embodiments of the present disclosure are not limited thereto.
[0445] The rare earth metal compound may 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 one or more embodiments, the rare earth metal compound may be selected from YbF 3 , ScF 3 , TbF 3 , YbI 3 , ScI 3 and TbI 3 , but the embodiments of the present disclosure are not limited thereto.
[0446] The alkali metal complex, alkaline earth metal complex and rare earth metal complex may respectively contain ions of alkali metals, alkaline earth metals and rare earth metals as described above, and the ligands coordinated with the metal ions of the alkali metal complex, alkaline earth metal complex or rare earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline and cyclopentadiene, but the embodiments of the present disclosure are not limited thereto.
[0447] The electron injection layer may include the following (e.g., may be composed of the following): alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex or any combination thereof as described above. In one or more than one embodiment, the electron injection layer may 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 any combination thereof may be uniformly or non-uniformly dispersed in a matrix comprising organic material.
[0448] The thickness of the electron injection layer can be about to about For example, about to about When the thickness of the electron injection layer is within these ranges, satisfactory (or suitable) electron injection characteristics can be obtained without a significant increase in driving voltage.
[0449] The second electrode 190
[0450] The second electrode 190 may be arranged (positioned) on the organic layer 150 having the structure according to the embodiment of the present disclosure. The second electrode 190 may be a cathode, which is an electron injection electrode, and in this regard, a material for forming the second electrode 190 may be selected from metals, alloys, conductive compounds, and combinations thereof having a relatively low work function.
[0451] 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 embodiments of the present disclosure are not limited thereto. The second electrode 190 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
[0452] The second electrode 190 may have a single-layer structure, or a multi-layer structure including two or more layers.
[0453] Figures 2 to 4 Description
[0454] Figure 2 is a schematic view of an organic light-emitting device 20 according to an embodiment. The organic light-emitting device 20 includes a first cover layer 210, a first electrode 110, an organic layer 150, and a second electrode 190, which are sequentially stacked in this prescribed order. Figure 3is a schematic view of an organic light-emitting device 30 according to an embodiment. The organic light-emitting device 30 includes a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220, which are sequentially stacked in this prescribed order. Figure 4 is a schematic view of an organic light-emitting device 40 according to an embodiment. The organic light-emitting device 40 includes a first cover layer 210, a first electrode 110, an organic layer 150, a second electrode 190, and a second cover layer 220, which are sequentially stacked in this prescribed order.
[0455] about Figures 2 to 4 The first electrode 110, the organic layer 150, and the second electrode 190 can be described by referring to Figure 1 Their descriptions are presented to understand.
[0456] In the organic layer 150 of each of the organic light-emitting devices 20 and 40, light generated in the emission layer may pass through the first electrode 110 and the first cover layer 210 toward the outside, wherein the first electrode 110 may be a semi-transmissive electrode or a transmissive electrode. In the organic layer 150 of each of the organic light-emitting devices 30 and 40, light generated in the emission layer may pass through the second electrode 190 and the second cover layer 220 toward the outside, wherein the second electrode 190 may be a semi-transmissive electrode or a transmissive electrode.
[0457] The first cover layer 210 and the second cover layer 220 may increase external light emitting efficiency according to the principle of constructive interference.
[0458] The first capping layer 210 and the second capping layer 220 may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or a composite capping layer including an organic material and an inorganic material.
[0459] At least one selected from the first cover layer 210 and the second cover layer 220 may each independently contain at least one material selected from carbocyclic compounds, heterocyclic compounds, amine-based compounds, porphyrin derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, and alkaline earth metal complexes. The carbocyclic compounds, heterocyclic compounds, and amine-based compounds may each independently be optionally substituted with a substituent containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In one or more embodiments, at least one selected from the first cover layer 210 and the second cover layer 220 may each independently contain an amine-based compound.
[0460] In one or more than one embodiments, at least one selected from the first cover layer 210 and the second cover layer 220 may each independently include the compound represented by Formula 201 or the compound represented by Formula 202.
[0461] In one or more than one embodiments, at least one selected from the first cover layer 210 and the second cover layer 220 may each independently include a compound selected from Compound HT28 to Compound HT33 and Compound CP1 to Compound CP5, but the embodiments of the present disclosure are not limited thereto:
[0462]
[0463] In the above, we have already discussed Figures 1 to 4 The organic light-emitting device according to one or more than one embodiments of the present disclosure is described, but the embodiments of the present disclosure are not limited thereto.
[0464] The layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region can be formed in a certain region 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.
[0465] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by vacuum deposition, the deposition temperature may be about 100° C. to about 500° C., about 10 -8 To about 10 -3 Torr vacuum and approx. to about Deposition is carried out at a deposition rate of .
[0466] When a layer constituting a hole transport region, an emission layer, and a layer constituting an electron transport region are formed by spin coating, spin coating can be performed at a coating speed of about 2,000 rpm to about 5,000 rpm and at a heat treatment temperature of about 80°C to 200°C by considering the material to be included in the layer to be formed and the structure of the layer to be formed.
[0467] General Definition of Substituents
[0468] As used herein, the term "C 1 -C 60 The term "alkyl group" may refer to a linear or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms, and non-limiting 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" may refer to a 1 -C 60 A divalent group of the same structure as an alkyl group.
[0469] As used herein, the term "C 2 -C 60 The term "alkenyl group" may refer to an 2 -C 60 At one or more than one position of the hydrocarbon chain of the alkyl group (e.g., at C 2 -C 60 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" may refer to a 2 -C 60 Alkenyl groups are divalent groups of the same structure.
[0470] As used herein, the term "C 2 -C 60 "Alkynyl group" may refer to 2 -C 60 At one or more than one position of the hydrocarbon chain of the alkyl group (e.g., at C 2 -C 60 In some embodiments, C 2 -C 60 The alkynyl group may be C 2 -C 30 Alkynyl group, C 2 -C 20 Alkynyl group or C 2 -C 10 As used herein, the term "C 2 -C 60"Alkyne group" may refer to a 2 -C 60 Alkynyl groups are divalent groups of the same structure.
[0471] As used herein, the term "C 1 -C 60 The term "alkoxy group" may refer to 101 (A 101 C 1 -C 60 The term "alkyl group" refers to a monovalent group represented by an alkyl group, and non-limiting examples thereof include a methoxy group, an ethoxy group, and an isopropyloxy group.
[0472] As used herein, the term "C 3 -C 10 The term "cycloalkyl group" as used herein may refer to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. 3 -C 10 The cycloalkylene group may refer to a 3 -C 10 Cycloalkyl groups are divalent groups of the same structure.
[0473] As used herein, the term "C 1 -C 10 The term “heterocycloalkyl group” may refer to a monovalent monocyclic group having at least one heteroatom (e.g., 1 to 5 or 1 to 3, such as 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, and non-limiting 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 The term "heterocycloalkylene group" may refer to a 1 -C 10 Heterocycloalkyl groups are divalent groups of the same structure.
[0474] As used herein, the term "C 3 -C 10 The term "cycloalkenyl group" as used herein may refer to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and having no aromaticity, and non-limiting examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. 3 -C 10 The "cycloalkenylene group" may refer to a 3 -C 10Cycloalkenyl groups are divalent groups of the same structure.
[0475] As used herein, the term "C 1 -C 10 The term "heterocycloalkenyl group" may refer to a monovalent monocyclic group having at least one heteroatom (e.g., 1 to 5 or 1 to 3, such as 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 carbon double bond in its ring. 1 -C 10 Non-limiting examples of heterocycloalkenyl groups include 4,5-dihydro-1,2,3,4-oxatriazolyl groups, 2,3-dihydrofuranyl groups, and 2,3-dihydrothienyl groups. As used herein, the term “C 1 -C 10 The term "heterocycloalkenylene group" may refer to a 1 -C 10 Heterocycloalkenyl groups are divalent groups of the same structure.
[0476] As used herein, the term "C 6 -C 60 The term "aryl group" may refer to a monovalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms. 6 -C 60 Non-limiting examples of aryl groups include phenyl groups, naphthyl groups, anthracenyl groups, phenanthrenyl groups, pyrenyl groups and In some embodiments, C 6 -C 60 The aryl group may be C 6 -C 30 Aryl group, C 6 -C 24 Aryl group or C 6 -C 18 Aryl group. As used herein, the term "C 6 -C 60 The term "arylene group" may refer to a 6 -C 60 A divalent group with the same structure as the aromatic group. 6 -C 60 Aryl groups and C 6 -C 60 When the arylene groups each independently include two or more rings, the respective rings may be fused to each other.
[0477] As used herein, the term "C 1 -C 60The term "heteroaryl group" may refer to a monovalent group having a carbocyclic aromatic system containing at least one heteroatom (e.g., 1 to 5 or 1 to 3, such as 1, 2, 3, 4 or 5 heteroatoms) selected from N, O, Si, P and S as a ring atom other than 1 to 60 carbon atoms. 1 -C 60 Non-limiting examples of heteroaryl groups include pyridyl groups, pyrimidinyl groups, pyrazinyl groups, pyridazinyl groups, triazinyl groups, quinolyl groups, and isoquinolyl groups. 1 -C 60 The heteroaryl group may be C 1 -C 30 Heteroaryl groups, C 1 -C 24 Heteroaryl groups or C 1 -C 18 As used herein, the term "C 1 -C 60 The term "heteroarylene group" may refer to a 1 -C 60 Heteroaryl groups are divalent groups of the same structure. 1 -C 60 Heteroaryl groups and C 1 -C 60 When the heteroarylene groups each independently contain two or more rings, the respective rings may be condensed / fused to each other.
[0478] As used herein, the term "C 6 -C 60 The "aryloxy group" may refer to 102 (A 102 C 6 -C 60 aryl group), and C 6 -C 60 The arylthio group may be represented by -SA 103 (A 103 C 6 -C 60 A monovalent group represented by an aryl group.
[0479] As used herein, the term "monovalent non-aromatic fused polycyclic group" may refer to a monovalent group (e.g., having 8 to 60 carbon atoms, such as 8 to 30 or 8 to 18 carbon atoms) having two or more rings fused to each other, having only carbon atoms as ring atoms, and not having aromaticity in its entire molecular structure. A non-limiting example of a monovalent non-aromatic fused polycyclic group is a fluorenyl group. As used herein, the term "divalent non-aromatic fused polycyclic group" may refer to a divalent group having the same structure as a monovalent non-aromatic fused polycyclic group.
[0480] The term "monovalent non-aromatic fused heteropolycyclic group" as used herein may refer to a monovalent group (e.g., having 1 to 60 carbon atoms, such as 1 to 30 or 1 to 18 carbon atoms), which has two or more rings fused to each other, has at least one heteroatom (e.g., 1 to 5 or 1 to 3, such as 1, 2, 3, 4 or 5 heteroatoms) selected from N, O, Si, P and S other than carbon atoms as a ring-forming atom, and does not have aromaticity in its entire molecular structure. A non-limiting example of a monovalent non-aromatic fused heteropolycyclic group is a carbazolyl group. The term "divalent non-aromatic fused heteropolycyclic group" as used herein may refer to a divalent group having the same structure as a monovalent non-aromatic fused heteropolycyclic group.
[0481] As used herein, the term "C 5 -C 60 A "carbocyclic group" may refer to a monocyclic group or a polycyclic group having 5 to 60 carbon atoms (e.g., 5 to 30 or 5 to 18 carbon atoms), wherein the ring atoms are only carbon atoms. As used herein, the term "C 5 -C 60 The term "carbocyclic group" may refer to an aromatic carbocyclic group or a non-aromatic carbocyclic group. 5 -C 60 The carbocyclic group may be a ring (e.g., benzene), a monovalent group (e.g., a phenyl group), or a divalent group (e.g., a phenylene group). 5 -C 60 The number of substituents in a carbocyclic group, C 5 -C 60 The carbocyclic group may be a trivalent group or a tetravalent group.
[0482] As used herein, the term "C 1 -C 60 A "heterocyclic group" may refer to a 5 -C 60The invention relates to a group having the same structure as a carbocyclic group, but in addition to carbon atoms (the number of carbon atoms can be 1 to 60, for example 5 to 30 or 5 to 18 carbon atoms), at least one heteroatom (for example 1 to 5 or 1 to 3, such as 1, 2, 3, 4 or 5 heteroatoms) selected from N, O, Si, P and S is used as a ring-forming atom.
[0483] In this specification, substituted C 5 -C 60 Carbocyclic 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 60 Aryloxy 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:
[0484] 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;
[0485] 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 -C 60 Alkenyl group, C 2 -C 60 Alkynyl groups and C 1 -C 60 Alkoxy groups;
[0486] C 3 -C 10Cycloalkyl 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;
[0487] 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 )(Q 23 )、-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
[0488] -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 ),as well as
[0489] 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, C1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 1 -C 60 a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.
[0490] The term "Ph" as used herein may refer to a phenyl group, the term "Me" as used herein may refer to a methyl group, the term "Et" as used herein may refer to an ethyl group, the term "ter-Bu" or "Bu" as used herein may refer to an ethyl group. t " may refer to a tert-butyl group, the term "OMe" as used herein may refer to a methoxy group, and "D" may refer to deuterium.
[0491] The term "biphenyl group" as used herein may refer to a "phenyl group substituted by a phenyl group". In other words, the "biphenyl group" is a phenyl group having C 6 -C 60 Aryl groups are substituted phenyl groups as substituents.
[0492] The term "terphenyl group" as used herein may refer to a "phenyl group substituted by a biphenyl group". In other words, the "terphenyl group" is a phenyl group having a C 6 -C 60 Aryl-substituted C 6 -C 60 Aryl groups are substituted phenyl groups as substituents.
[0493] Unless otherwise defined, * and *' as used herein each refer to a site of attachment to an adjacent atom in the corresponding formula.
[0494] Hereinafter, the compound according to the embodiment and the organic light-emitting device according to the embodiment will be described in more detail with reference to Synthesis Examples and Examples. The phrase "using B instead of A" used in describing Synthesis Examples may mean using B instead of A in an equimolar amount.
[0495] Example
[0496] Synthesis example
[0497] Synthesis Example 1: Synthesis of Compound 14
[0498]
[0499] Synthesis of Intermediate 14-1
[0500] N-(3,5-dibromophenyl)-N-phenyldibenzo[b,d]furan-1-amine (1 equivalent), N,9-diphenyl-9H-carbazole-4-amine (2 equivalents), tris(dibenzylideneacetone)dipalladium(0) (0.1 equivalent), tri-tert-butylphosphine (0.2 equivalent) and sodium tert-butoxide (5 equivalents) were dissolved in toluene and stirred at a temperature of 100° C. for 12 hours. After the reaction mixture was cooled, the reaction mixture was washed three times by using ethyl acetate and water to obtain an organic layer. The organic layer was washed by using MgSO 4 Dry under reduced pressure. The product thus obtained was purified by column chromatography to obtain Intermediate 14-1 (yield: 65%).
[0501] Synthesis of compound 14
[0502] Intermediate 14-1 (1 equivalent) was dissolved in o-dichlorobenzene, and the reaction mixture was cooled to a temperature of 0°C. 3 14 (yield: 20%).
[0503] Synthesis Example 2: Synthesis of Compound 20
[0504]
[0505] Synthesis of Intermediate 20-1
[0506] Intermediate 20-1 was obtained in the same (or substantially the same) manner as in the synthesis of Intermediate 14-1 (yield: 71%), except that N-(3,5-dibromophenyl)-N-phenyldibenzo[b,d]thiophene-1-amine was used instead of N-(3,5-dibromophenyl)-N-phenyldibenzo[b,d]furan-1-amine.
[0507] Synthesis of compound 20
[0508] Compound 20 was obtained (yield: 29%) in the same (or substantially the same) manner as in the synthesis of Compound 14, except that Intermediate 20-1 was used instead of Intermediate 14-1.
[0509] Synthesis Example 3: Synthesis of Compound 107
[0510]
[0511] Synthesis of Intermediate 107-1
[0512] Intermediate 107-1 was obtained in the same (or substantially the same) manner as in the synthesis of intermediate 14-1 (yield: 64%), except that N-isopropyl-9-phenyl-9H-carbazole-4-amine (3 equivalents) was used instead of N,9-diphenyl-9H-carbazole-4-amine (2 equivalents), and tribromobenzene (1 equivalent) was used instead of N-(3,5-dibromophenyl)-N-phenyldibenzo[b,d]furan-1-amine (1 equivalent).
[0513] Synthesis of compound 107
[0514] Compound 107 (yield: 14%) was obtained in the same (or substantially the same) manner as in the synthesis of Compound 14, except that Intermediate 107-1 was used instead of Intermediate 14-1.
[0515] Synthesis Example 4: Synthesis of Compound 114
[0516]
[0517] Synthesis of Intermediate 114-1
[0518] Intermediate 114-1 was obtained in the same (or substantially the same) manner as in the synthesis of Intermediate 107-1 (yield: 65%), except that N-(2,6-dimethylphenyl)-9-phenyl-9H-carbazole-4-amine (3 equiv.) was used instead of N-isopropyl-9-phenyl-9H-carbazole-4-amine (3 equiv.).
[0519] Synthesis of compound 114
[0520] Compound 114 was obtained in the same (or substantially the same) manner as in the synthesis of Compound 14 (yield: 20%), except that Intermediate 114-1 was used instead of Intermediate 14-1.
[0521] Synthesis Example 5: Synthesis of Compound 115
[0522]
[0523] Synthesis of Intermediate 115-1
[0524] Intermediate 115-1 was obtained in the same (or substantially the same) manner as in the synthesis of Intermediate 107-1 (yield: 58%), except that N-(2,6-dimethylphenyl)dibenzo[b,d]furan-1-amine (3 equiv.) was used instead of N-isopropyl-9-phenyl-9H-carbazole-4-amine (3 equiv.).
[0525] Synthesis of compound 115
[0526] Compound 115 was obtained in the same (or substantially the same) manner as in the synthesis of Compound 14 (yield: 12%), except that Intermediate 115-1 was used instead of Intermediate 14-1.
[0527] Synthesis Example 6: Synthesis of Compound 116
[0528]
[0529] Synthesis of Intermediate 116-1
[0530] Intermediate 116-1 was obtained in the same (or substantially the same) manner as in the synthesis of Intermediate 107-1 (yield: 52%), except that N-(2,6-dimethylphenyl)dibenzo[b,d]thiophene-1-amine (3 equiv.) was used instead of N-isopropyl-9-phenyl-9H-carbazole-4-amine (3 equiv.).
[0531] Synthesis of compound 116
[0532] Compound 116 was obtained in the same (or substantially the same) manner as in the synthesis of Compound 14 (yield: 24%), except that Intermediate 116-1 was used instead of Intermediate 14-1.
[0533] Synthesis Example 7: Synthesis of Compound 117
[0534]
[0535] Synthesis of Intermediate 117-1
[0536] Intermediate 117-1 was obtained in the same (or substantially the same) manner as in the synthesis of Intermediate 14-1 (yield: 52%), except that N-mesityl-9-phenyl-9H-carbazole-4-amine was used instead of N,9-diphenyl-9H-carbazole-4-amine, and N-(3,5-dibromophenyl)-N-mesityldibenzo[b,d]thiophene-1-amine was used instead of N-(3,5-dibromophenyl)-N-phenyldibenzo[b,d]furan-1-amine.
[0537] Synthesis of compound 117
[0538] Compound 117 was obtained in the same (or substantially the same) manner as in the synthesis of Compound 14 (yield: 22%), except that Intermediate 117-1 was used instead of Intermediate 14-1.
[0539] The compounds synthesized according to Synthesis Examples 1 to 7 1 H NMR and (Fast Atom Bombardment Mass Spectrometry) MS / FAB are shown in Table 1.
[0540] By referring to the synthetic mechanisms and source materials described above, the synthesis methods of compounds other than those shown in Table 1 should be readily recognized by those of ordinary skill in the art.
[0541] Table 1
[0542]
[0543]
[0544] Evaluation Example
[0545] Evaluation Example 1: Evaluation of properties of TADF compounds
[0546] The HOMO energy levels (E) of the compounds synthesized according to Synthesis Examples 1 to 7, as well as Compounds A to F and Compound DABNA-1 were obtained by quantum chemical calculation. HOMO ), LUMO energy level (E LUMO ), energy gap (E g ), T1 energy level, S1 energy level and oscillator strength. Quantum chemical calculations were performed using Gaussian 09 based on DFT (B3LYP / 6-31G*) calculations.
[0547] Table 2
[0548]
[0549]
[0550]
[0551]
[0552] From the results of Table 1, it is confirmed that the compounds according to one or more than one embodiments have small ΔE compared to the related compounds DABNA-1 and compounds A to F. st and the usual increase in oscillator strength,
[0553] Evaluation Example 2: Evaluation of device performance
[0554] Example 1
[0555] Corning 15Ω / cm 2 The ITO glass substrate was cut into a size of 50 mm×50 mm×0.7 mm, ultrasonically treated with isopropyl alcohol and pure water for 5 minutes each, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes. Then, the ITO glass substrate was provided to a vacuum deposition apparatus. Compound NPD was vacuum deposited on the ITO glass substrate to form a A hole injection layer having a thickness of , and a hole transport compound TCTA is vacuum deposited on the hole injection layer to form a The hole transport compound CzSi is vacuum deposited on the first hole transport layer to form a The mCP and compound 14 were co-deposited on the second hole transport layer at a weight ratio of 99:1 to form a Then, TSPO1 is deposited on the emission layer to form an emission layer having a thickness of A buffer layer having a thickness of , and an electron transport compound TPBI is deposited on the buffer layer to form a The alkali metal halide LiF is deposited on the electron transport layer to form a The electron injection layer is formed by vacuum deposition of Al (cathode electrode) to A LiF / Al electrode is formed with a thickness of , thereby completing the manufacture of an organic light-emitting device.
[0556]
[0557] Example 2 to Example 7
[0558] An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Example 1, except that the compounds shown in Table 3 were each used to form an emission layer.
[0559] Comparative Examples 1 to 5
[0560] An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Example 1, except that Compound DABNA-1 and Compounds A to D were each used to form an emission layer.
[0561]
[0562] At 10mA / cm 2 The driving voltage (V), efficiency (cd / A), and maximum quantum efficiency (%) of the organic light-emitting devices manufactured according to Examples 1 to 7 and Comparative Examples 1 to 5 were measured, and the results are shown in Table 3.
[0563] Table 3
[0564]
[0565] From the results of Table 3, it is confirmed that the organic light-emitting devices of Examples 1 to 7, in which the compounds according to one or more embodiments are used as dopants for the emission layer, have low driving voltages and improved luminous efficiency and maximum quantum efficiency, compared to the organic light-emitting devices of Comparative Examples 1 to 5. In addition, it is confirmed that the organic light-emitting devices of Examples 1 to 7 emit blue light with high color purity, compared to the organic light-emitting devices of Comparative Examples 3 and 4.
[0566] That is, when the compound according to one or more than one embodiments is used in an electronic device (eg, an organic light-emitting device), excellent effects may be exhibited in terms of driving voltage and efficiency.
[0567] An organic light-emitting device including the fused cyclic compound may have low driving voltage, high efficiency, and a long lifetime.
[0568] As used herein, the terms "use," "using," and "used" may be considered synonymous with the terms "utilize," "utilizing," and "utilized," respectively.
[0569] Furthermore, the terms "substantially," "about," and similar terms are used as terms of approximation rather than terms of degree, and are intended to account for the inherent variations in measurements or calculations that would be recognized by those of ordinary skill in the art.
[0570] 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, 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 clearly list any sub-ranges included in the scope clearly listed herein.
[0571] 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 typically be considered as available for other similar features or aspects in other embodiments.
[0572] 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 of the present disclosure as defined by the claims and their equivalents.
Claims
1. An organic light-emitting device, comprising: a first electrode; a second electrode facing the first electrode; an organic layer between the first electrode and the second electrode, the organic layer comprising an emission layer; and at least one fused cyclic compound represented by Formula 1, The emission layer comprises a phosphorescent dopant, a fluorescent dopant, or a phosphorescent dopant and a fluorescent dopant: Formula 1 Among them, in formula 1, Y1 is C(R1), Y2 is C(R2), Y3 is C(R3), Y4 is C(R4), Y5 is C(R5), Y6 is C(R6), Y7 is C(R7), Y8 is C(R8), Y9 is C(R9), Y 10 C(R 10 ), Y 11 C(R 11 ), Y 12 C(R 12 ), Y 13 C(R 13 ), Y 14 C(R 14 ), and Y 15 C(R 15 ), R1 and R3 to R 15 are each independently hydrogen, R2 is a group represented by formula 2, X1 is selected from O, S and N (R 16 ), X2 is selected from O, S and N (R 18 ), Formula 2 Among them, in formula 1 and formula 2, L1 to L3 are each independently a single bond, a1 to a3 are each independently 1, X3 is selected from O, S and N (R 22 ), A1 is a benzene ring group, Ar1 to Ar3 are each independently selected from substituted or unsubstituted C1-C 60 Alkyl groups and substituted or unsubstituted C6-C 60 Aryl groups, R 20 and R 21 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 carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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 groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic groups, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) and -P(=O)(Q1)(Q2), R 16 , R 18 and R 22 are each independently selected from 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 groups, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic groups, b20 is an integer from 1 to 3, b21 is an integer from 1 to 6, 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)(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, and monovalent non-aromatic fused heteropolycyclic 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)(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)(Q 31 )、-S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ), and Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 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 group, C1-C 60 a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.
2. The organic light emitting device according to claim 1, wherein The phosphorescent dopant includes an organic metal complex represented by Formula 401: Formula 401 M(L 401 ) xc1 (L 402 ) xc2 In formula 401, M is selected from iridium, platinum, palladium, osmium, titanium, zirconium, hafnium, europium, terbium, rhodium and thulium, L 401 is selected from the ligand represented by formula 402, and xc1 is 1, 2 or 3, wherein, When xc1 is 2 or greater, two or more L 401 Same or different from each other, L 402 is an organic ligand, and xc2 is an integer from 0 to 4, wherein when xc2 is two or more than two, two or more L 402 Same or different from each other Formula 402 In formula 402, X 401 To X 404 are each independently nitrogen or carbon, X 401 and X 403 optionally linked via a single bond or a double bond, and X 402 and X 404 optionally linked via a single bond or a double bond, A 401 and A 402 Each independently selected from C5-C 60 Carbocyclic groups and C1-C 60 Heterocyclic groups, X 405 is a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 411 )-*'、*-C(Q 411 )(Q 412 )-*'、*-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 )=*'or*=C=*', X 406 is a single bond, O or S, R 401 and R 402 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 substituted or unsubstituted C1-C 20 Alkyl groups, substituted or unsubstituted C1-C 20 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(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O)2(Q 401 ) and -P(=O)(Q 401 )(Q 402 ), where Q 401 To Q 403 Each independently selected from C1-C 10 Alkyl groups, C1-C 10 Alkoxy groups, C6-C 20 Aryl groups and C1-C 20 Heteroaryl groups, The substituted C1-C 20 Alkyl group, the substituted C1-C 20 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 20 Alkyl groups and C1-C 20 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)(Q 11 )、-S(=O)2(Q 11 ) and -P(=O)(Q 11 )(Q 12 ) at least one substituted C1-C 20 Alkyl groups and C1-C 20 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, and monovalent non-aromatic fused heteropolycyclic 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 20 Alkyl groups, C1-C 20 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)(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)(Q 31 )、-S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ), and Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 , Q 31 To Q 33 , Q 401 To Q 403 , Q 411 and Q 412 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 group, C1-C 60 heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups and terphenyl groups, xc11 and xc12 are each independently an integer from 0 to 10, and * and *' in Formula 402 each represent a bonding site to M in Formula 401.
3. The organic light emitting device according to claim 2, wherein In formula 402, i)X 401 is nitrogen, and X 402 for carbon, or ii)X 401 and X 402 Each is nitrogen.
4. The organic light emitting device according to claim 2, wherein R in Formula 402 401 and R 402 Each independently selected from: Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups and C1-C 20 Alkoxy groups; C1-C ... 20 Alkyl groups and C1-C 20 Alkoxy groups; a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; 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 20 Alkyl groups, C1-C 20 a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group substituted with at least one of an alkoxy group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O)2(Q 401 ) and -P(=O)(Q 401 )(Q 402 ), and Q 401 To Q 403 Each independently selected from C1-C 10 Alkyl groups, C1-C 10 an alkoxy group, a phenyl group, a biphenyl group, and a naphthyl group.
5. The organic light emitting device according to claim 2, wherein The phosphorescent dopant includes at least one compound selected from Compound PD1 to Compound PD25:
6. The organic light emitting device according to claim 1, wherein The fluorescent dopant includes at least one of the compounds represented by Formula 501: Formula 501 In formula 501, Ar 501 is substituted or unsubstituted C5-C 60 Carbocyclic group or substituted or unsubstituted C1-C 60 Heterocyclic groups, L 501 To L 503 are each independently selected from substituted or unsubstituted C3-C 10 Cycloalkylene group, substituted or unsubstituted C1-C 10 Heterocycloalkylene group, substituted or unsubstituted C3-C 10 Cycloalkenylene group, substituted or unsubstituted C1-C 10 Heterocycloalkenylene group, substituted or unsubstituted C6-C 60 Arylene group, substituted or unsubstituted C1-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, xd1 to xd3 are each independently an integer from 0 to 3, R 501 and R 502 are each independently selected from 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 a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, and xd4 is an integer from 1 to 6.
7. The organic light emitting device according to claim 6, wherein In formula 501, Ar 501 Selected from: naphthyl group, heptalene 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, and an indenophenanthrene group; and 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 20 Alkyl groups, C1-C 20 a naphthyl group substituted with at least one of an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group, a heptalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, group, a naphthacene group, a phenanthrene group, a perylene group, a pentaphenyl group, an indenoanthracene group and an indenophenanthrene group.
8. The organic light emitting device according to claim 6, wherein In formula 501, L 501 To L 503 Each independently selected from: 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 benzothienylene group, a dibenzofuranylene group, a dibenzothienylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilylene group, and a pyridylene group; and 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 20 Alkyl groups, C1-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, The invention also includes at least one substituted phenylene group, naphthyl group, fluorenyl group, spiro-difluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, anthracen ... The invention also includes but is not limited to: 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 benzothienylene group, a dibenzofuranylene group, a dibenzothienylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilylene group, and a pyridylene group.
9. The organic light emitting device according to claim 6, wherein In formula 501, R 501 and R 502 Each independently selected from: 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 benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilyl group, and a pyridyl group; and 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 20 Alkyl groups, C1-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 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, and -Si(Q) 31 )(Q 32 )(Q 33 ) 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 benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilyl group, and a pyridyl group, and Q 31 To Q 33 Each independently selected from C1-C 10 Alkyl groups, C1-C 10 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.
10. The organic light emitting device according to claim 6, wherein In formula 501, xd4 is 2.
11. The organic light emitting device according to claim 6, wherein The fluorescent dopant includes at least one compound selected from the group consisting of compounds FD1 to FD22, DPVBi, DPAVBi, TBPe, DCM, DCJTB, coumarin 6, and C545T:
12. The organic light emitting device according to claim 1, wherein The first electrode is an anode, The second electrode is a cathode, The organic layer comprises the condensed cyclic compound, The organic layer further includes a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode, The hole transport region includes a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof, and The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
13. The organic light emitting device according to claim 1, wherein The emission layer includes the condensed cyclic compound.
14. The organic light emitting device according to claim 1, wherein The emission layer will emit blue light having a maximum emission wavelength of 420 nm or more and 480 nm or less.
15. The organic light emitting device according to claim 12, wherein The hole transport region includes a hole transport layer, and The hole transport layer includes a first hole transport layer and a second hole transport layer.
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Laser welding method for joining solid and porous metal components
KR1020190041497A