Organic light-emitting devices and compounds
By substituting carbazole derivatives at specific positions with aromatic groups and amino groups, the luminous efficiency of organic light-emitting devices is enhanced, addressing the inefficiencies in existing compounds.
Patent Information
- Application Number
- CN201911256492.X
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2019-02-13
- Filing Date
- 2019-12-10
- Publication Date
- 2025-01-03
- Estimated Expiration
- 2039-12-10
AI Technical Summary
Existing organic light-emitting devices using phenylenediamine and arylamine compounds with carbazole groups for hole injection and transport layers suffer from insufficient luminous efficiency.
Incorporating a carbazole derivative with specific substituents at the 2- and 3-positions and an aromatic group at the 9-position to enhance the hole transport compound, stabilizing the molecule electronically and increasing effective conjugation.
The modified carbazole derivative compounds improve luminous efficiency and thermal characteristics, leading to more effective organic light-emitting devices.
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Figure CN111564562B_ABST
Abstract
Description
[0001] This application claims the benefit of Korean Patent Application No. 10-2019-0016836 filed on February 13, 2019, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field
[0002] One or more embodiments of the present disclosure are directed to an organic light emitting device including an organic layer including a carbazole derivative compound. Background Art
[0003] Compared to other devices in the art, organic light emitting devices are self-emissive devices that have wide viewing angles, high contrast, short response times, and excellent characteristics in terms of brightness, driving voltage, and / or response speed, and can produce full-color images.
[0004] An example of such an organic light-emitting device may include a first electrode disposed (e.g., placed or positioned) on a substrate and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially disposed on the first electrode. Holes provided from the first electrode may move toward the emission layer through the hole transport region, and electrons provided from the second electrode may move toward the emission layer through the electron transport region. Carriers such as holes and electrons may then recombine in the emission layer to generate excitons. The excitons then transition from an excited state to a ground state, thereby generating light.
[0005] In the prior art, a phenylenediamine structure is disclosed as a hole injection material that can be used for an organic light-emitting device. As hole transport materials, aromatic diamine derivatives and / or aromatic condensed ring diamine derivatives are known. As improved (or derived) compounds from these compounds, arylamine compounds containing carbazole have been disclosed and used as hole transport materials. In addition, arylamine compounds having a carbazole group substituted at position 3 have been disclosed and used as hole injection materials.
[0006] However, since devices in which these compounds are used for a hole injection layer and / or a hole transport layer generally have insufficient luminous efficiency, improved luminous efficiency characteristics are required. Summary of the invention
[0007] One or more aspects of embodiments of the present disclosure relate to hole transport compounds having improved luminous efficiency characteristics compared to comparable compounds and organic light emitting devices including the hole transport compounds.
[0008] Additional embodiments will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the presented embodiments.
[0009] An embodiment of the present disclosure provides an organic light-emitting device, the organic light-emitting device comprising:
[0010] a first electrode;
[0011] a second electrode facing the first electrode; and
[0012] an organic layer, located between the first electrode and the second electrode, the organic layer comprising an emission layer,
[0013] wherein the organic layer comprises a carbazole derivative,
[0014] From substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 1 -C 60 A substituent selected from a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group is attached to the 2-position of the carbazole group of the carbazole derivative,
[0015] The amino substituent is directly or indirectly connected to the 3-position of the carbazole group of the carbazole derivative, and
[0016] Substituted or unsubstituted C 6 -C 60 The aryl group is bonded to the 9-position of the carbazole group of the carbazole derivative.
[0017] Another aspect of the present disclosure provides a compound represented by Formula 1:
[0018] Formula 1
[0019]
[0020] In formula 1,
[0021] R 1 and R 4 To R 8 can be independently selected from hydrogen, deuterium, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, R 2 ,Ar 1 and Ar 2 can be independently selected from substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 1 -C 60heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, R 9 Can be selected from substituted or unsubstituted C 6 -C 60 Aryl,
[0022] L can be selected from single bonds, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0023] Substituted C 6 -C 60 Aryl, substituted C 1 -C 60 Heteroaryl, substituted monovalent non-aromatic condensed polycyclic group, substituted monovalent non-aromatic condensed heteropolycyclic group, substituted C 6 -C 60 Arylene, substituted C 1 -C 60 At least one substituent in the heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group and the substituted divalent non-aromatic condensed heteropolycyclic group may be selected from:
[0024] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;
[0025] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed 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 ) selected from at least one of the C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;
[0026] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups;
[0027] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed 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 ) selected from at least one of the C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and
[0028] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),and
[0029] Q 11 To Q13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups and terphenyl groups.
[0030] Another embodiment of the present disclosure provides an electronic device, which includes a thin film transistor and the above-mentioned organic light-emitting device, wherein the thin film transistor includes a source electrode, a drain electrode, an active layer and a gate electrode, and the first electrode of the organic light-emitting device is electrically contacted with one of the source electrode and the drain electrode of the thin film transistor. BRIEF DESCRIPTION OF THE DRAWINGS
[0031] These and / or other aspects will become apparent and more easily understood through the following description of the embodiments in conjunction with the accompanying drawings, in which:
[0032] Figure 1 is a schematic diagram of an organic light emitting device according to an embodiment;
[0033] Figure 2 is a schematic diagram of an organic light emitting device according to an embodiment;
[0034] Figure 3 is a schematic diagram of an organic light emitting device according to an embodiment; and
[0035] Figure 4 is a schematic diagram of an organic light emitting device according to an embodiment. DETAILED DESCRIPTION
[0036] Now will be more detailed with reference to embodiment, the example of embodiment is shown in the accompanying drawings, wherein the same reference numerals represent the same element from time to time. In this regard, the present embodiment can have different forms, and should not be construed as being limited to the description set forth herein. Therefore, the embodiment is described below only by reference to the accompanying drawings to explain the many aspects of this specification. As used herein, the term "and / or" includes any combination and all combinations of one or more of the relevant listed items. When such as "at least one (kind / person) in ...", "one (kind / person) in ..." and "select (selected from ...) from ..." are expressed after (or before) a column of elements (elements), the entire column of elements (elements) is modified, and the individual elements (elements) in the column are not modified. In addition, when describing an embodiment of the present invention, the use of "can" can refer to "one or more embodiments of the present invention".
[0037] The organic light emitting device according to the embodiment includes: a first electrode; a second electrode facing the first electrode; and an organic layer located between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes a carbazole derivative, which is selected from substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 1 -C 60 A substituent selected from a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group is attached to the 2-position of the carbazole group of the carbazole derivative, an amino substituent is directly or indirectly attached to the 3-position of the carbazole group of the carbazole derivative, and a substituted or unsubstituted C 6 -C 60 The aryl group is bonded to the 9-position of the carbazole group of the carbazole derivative.
[0038] The position numbering of the carbazole group follows a general numbering sequence, the details of which are as follows:
[0039]
[0040] The term "directly or indirectly connected" may mean that the amino substituent is directly connected to carbazole, or that a divalent connecting group (eg, L in Formula 1) is first connected to carbazole and then the amino substituent is connected to the divalent connecting group.
[0041] The amino-type substituent may refer to a substituent in which one hydrogen and one substituent other than hydrogen are bonded to N, or a substituent in which two substituents other than hydrogen are bonded to N. The amino-type substituent may be, for example, a diarylamino group.
[0042] An embodiment of the present disclosure provides a heterocyclic compound represented by Formula 1:
[0043] Formula 1
[0044]
[0045] In formula 1,
[0046] R 1 and R 4 To R 8 can be independently selected from hydrogen, deuterium, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, R 2 ,Ar 1 and Ar 2 can be independently selected from substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, R 9 Can be selected from substituted or unsubstituted C 6 -C 60 Aryl,
[0047] L can be selected from single bonds, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0048] Substituted C 6 -C 60 Aryl, substituted C 1 -C 60 Heteroaryl, substituted monovalent non-aromatic condensed polycyclic group, substituted monovalent non-aromatic condensed heteropolycyclic group, substituted C 6 -C 60 Arylene, substituted C 1 -C 60 At least one substituent in the heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group and the substituted divalent non-aromatic condensed heteropolycyclic group may be selected from:
[0049] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;
[0050] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed 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 (Q11) and -P(=O)(Q 11 )(Q 12 ) selected from at least one of the C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;
[0051] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C6 -C 60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups;
[0052] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed 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 ) selected from at least one of the C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C6 -C 60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and
[0053] -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
[0054] 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, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups and terphenyl groups.
[0055] In one or more embodiments, in Formula 1, R 1 and R 4 To R 8 and may each independently be hydrogen or deuterium.
[0056] In the existing compounds in which substituents are linked at the 1-position and 3-position of the carbazole moiety, thermal characteristics and electrochemical characteristics are relatively insufficient compared to compounds in which substituents are linked at the 2-position and 3-position.
[0057] According to the present embodiment, the compound represented by Formula 1 has substituents at positions 2, 3, and 9 of the carbazole group. By substituting the amino group at the 3-position, a structure in which the compound in a cationic state is stable can be achieved, and by substituting the aromatic group at the 2-position, effective conjugation is increased, thereby stabilizing the resulting molecule electronically.
[0058] In one or more embodiments, R in Formula 1 9 It can be expressed by formula 2a:
[0059]
[0060] In formula 2a,
[0061] R 11 It can be selected from hydrogen, deuterium, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -C(Q1)(Q2)(Q 3 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ),
[0062] a11 can be an integer from 1 to 4,
[0063] Substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 At least one substituent in the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:
[0064] Deuterium, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;
[0065] All substituted with deuterium, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -O(Q 11 )、-S(Q 11 )、-Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-P(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 ) and -P(=O)(Q 11 )(Q 12 ) selected from at least one of the C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;
[0066] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups;
[0067] All substituted with deuterium, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -O(Q 21 )、-S(Q 21 )、-Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-P(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 ) and -P(=O)(Q 21 )(Q 22 ) selected from at least one of the C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and
[0068] -O(Q 31 )、-S(Q 31)、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),
[0069] 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, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group, and
[0070] *Indicates the binding site with the adjacent atom.
[0071] In one or more embodiments, R in Formula 1 2 It can be expressed by one selected from Formula 3a to Formula 3c:
[0072]
[0073] In Formula 3a to Formula 3c,
[0074] R21 To R 23 can be independently selected from substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -C(Q 1 )(Q 2 )(Q 3 )、-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 ),
[0075] X 1 Can be O, S or CR 51 R 52 ,
[0076] R 51 and R 52 can be independently selected from substituted or unsubstituted C 1 -C 60Alkyl, substituted or unsubstituted C 6 -C 60 Aryl and substituted or unsubstituted C 1 -C 60 Heteroaryl,
[0077] a21 can be an integer from 1 to 4,
[0078] a22 and a23 may each independently be an integer from 1 to 6,
[0079] Substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 At least one substituent in the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:
[0080] Deuterium, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;
[0081] All substituted with deuterium, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -O(Q 11 )、-S(Q 11 )、-Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-P(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 ) and -P(=O)(Q 11 )(Q 12 ) selected from at least one of the C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;
[0082] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups;
[0083] All substituted with deuterium, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -O(Q 21 )、-S(Q 21 )、-Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-P(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 ) and -P(=O)(Q 21 )(Q 22 ) selected from at least one of the C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and
[0084] -O(Q 31 )、-S(Q 31)、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),
[0085] 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, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group, and
[0086] *Indicates the binding site with the adjacent atom.
[0087] In one or more embodiments, in Formula 1, Ar 1 and Ar 2 can be independently represented by one selected from Formula 4a to Formula 4d:
[0088]
[0089] In Formula 4a to Formula 4d,
[0090] R 31 To R 34 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -C(Q 1 )(Q 2 )(Q 3 )、-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 ),
[0091] X 2 Can be O, S or CR 53 R 54 ,
[0092] R 53 and R 54can be independently selected from substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 6 -C 60 Aryl and substituted or unsubstituted C 1 -C 60 Heteroaryl,
[0093] a31 can be an integer from 1 to 4,
[0094] a32 and a34 may each independently be an integer from 1 to 6,
[0095] a33 can be an integer from 1 to 8, and
[0096] Substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 At least one substituent in the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:
[0097] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;
[0098] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -O(Q 11 )、-S(Q 11 )、-Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-P(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 ) and -P(=O)(Q 11 )(Q 12 ) selected from at least one of the C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;
[0099] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups;
[0100] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -O(Q 21 )、-S(Q 21 )、-Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-P(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 ) and -P(=O)(Q 21 )(Q 22 ) selected from at least one of the C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6-C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and
[0101] -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),
[0102] 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, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group, and
[0103] *Indicates the binding site with the adjacent atom.
[0104] In one or more embodiments, L in Formula 1 may be a single bond or a group represented by Formula 5a:
[0105]
[0106] In Formula 5a, * indicates a bonding site with an adjacent atom.
[0107] In one or more embodiments, R in Formula 1 9 It can be phenyl. For example, Formula 1 can be represented by Formula 2:
[0108] Formula 2
[0109]
[0110] In one or more embodiments, L in Formula 1 may be a single bond. For example, Formula 1 may be represented by Formula 3:
[0111] Formula 3
[0112]
[0113] In one or more embodiments, R in Formula 1 2 and R 9 Both may be phenyl. For example, Formula 1 may be represented by Formula 4:
[0114] Formula 4
[0115]
[0116] In Formula 2 to Formula 4, Ar 1 To Ar 4 and L may each independently be the same as defined in conjunction with Formula 1.
[0117] In one or more embodiments, in Formula 1, Ar 1 and Ar 2 One of the 2 and R 9 Both may be phenyl.
[0118] In one or more embodiments, the carbazole derivative represented by Formula 1 may be selected from Compound 1 to Compound 84:
[0119]
[0120]
[0121]
[0122]
[0123] The expression “(organic layer) includes at least one compound” as used herein may include the case where “(organic layer) includes one or more identical compounds represented by Formula 1” or the case where “(organic layer) includes two or more different compounds represented by Formula 1”.
[0124] For example, the organic layer may include only compound 1 as a compound of formula 1. In this regard, compound 1 may be present only in (e.g., may be included only in) the emission layer of the organic light-emitting device. In one or more embodiments, the organic layer may include compound 1 and compound 2 as compounds of formula 1. In one or more embodiments, both compound 1 and compound 2 may be present in (e.g., may be included in) the same (same) layer (e.g., both compound 1 and compound 2 may be present in the emission layer), or may be present in different layers (e.g., compound 1 may be present in the emission layer, and compound 2 may be present in the electron transport region).
[0125] An embodiment of the present disclosure provides an organic light-emitting device, the organic light-emitting device comprising:
[0126] a first electrode;
[0127] a second electrode facing the first electrode; and
[0128] an organic layer, located between the first electrode and the second electrode,
[0129] The organic layer includes an emission layer and a compound represented by Formula 1.
[0130] In one or more embodiments, in an organic light emitting device,
[0131] The first electrode may be an anode,
[0132] The second electrode may be a cathode,
[0133] 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.
[0134] The hole transport region may include a hole injection layer, a hole transport layer, a buffer layer, an electron blocking layer, or any one or more combinations thereof, and
[0135] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any one or more combinations thereof.
[0136] In one or more embodiments, the emissive layer may be a fluorescent emissive layer.
[0137] In one or more embodiments, the compound represented by Formula 1 may be used in a hole transport region, for example, may be used in a hole transport layer.
[0138] Another embodiment of the present disclosure provides an electronic device, the electronic device comprising:
[0139] Thin film transistors; and
[0140] The organic light emitting device of this embodiment,
[0141] The thin film transistor includes a source electrode, a drain electrode, an active layer and a gate electrode, and the first electrode of the organic light emitting device is electrically in contact with (eg, electrically coupled to) one selected from the source electrode and the drain electrode of the thin film transistor.
[0142] The term "organic layer" as used herein may refer to a single layer and / or a plurality of layers disposed 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.
[0143] Figure 1 Description
[0144] Figure 1 is a schematic cross-sectional view of an organic light emitting device 10 according to an embodiment of the present disclosure. The organic light emitting device 10 includes a first electrode 110, an organic layer 150, and a second electrode 190.
[0145] In the following, we will combine Figure 1 A structure of an organic light emitting device 10 according to an embodiment of the present disclosure and a method of manufacturing the organic light emitting device 10 according to an embodiment of the present disclosure are described.
[0146] First electrode 110
[0147] exist Figure 1 In the embodiment, a substrate may be additionally disposed below the first electrode 110 or above the second electrode 190. To be used as a substrate, the substrate may be a glass substrate and / or a plastic substrate having excellent (or suitable) mechanical strength, thermal stability, transparency, surface flatness, ease of handling, and / or waterproofness.
[0148] 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.
[0149] 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, the material used to form the first electrode 110 may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), and combinations thereof, but the embodiments of the present disclosure are not limited thereto. In one or more 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 combinations thereof, but the embodiments of the present disclosure are not limited thereto.
[0150] 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.
[0151] Organic layer 150
[0152] The organic layer 150 may be disposed on the first electrode 110. The organic layer 150 may include an emission layer.
[0153] 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 .
[0154] Hole transport region in the organic layer 150
[0155] The hole 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 multilayer structure having a plurality of layers including a plurality of different materials.
[0156] The hole transport region may include at least one layer selected from a hole injection layer, a hole transport layer, an emission auxiliary layer, and an electron blocking layer.
[0157] For example, the hole transport region may have a single-layer structure or a multi-layer structure, wherein the single-layer structure includes a single layer comprising a plurality of different materials, and the multi-layer structure has a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission assisting layer structure, a hole injection layer / emission assisting layer structure, a hole transport layer / emission assisting layer structure or a hole injection layer / hole transport layer / emission assisting layer structure, wherein, for each structure, the constituent layers are stacked sequentially (e.g., layered) from the first electrode 110 in the order stated, but the structure of the hole transport region is not limited thereto.
[0158] The hole transport region may include a layer including the compound represented by Formula 1.
[0159] In one or more embodiments, 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), and polyaniline / poly(4-styrenesulfonate) (PANI / PSS):
[0160]
[0161]
[0162] The thickness of the hole transport region can be approximately To about In the range of, 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 in the range of about To about In the range of, for example, about To about In the range of To about In the range of, 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 appropriate) hole transport characteristics may be obtained without significantly increasing the driving voltage.
[0163] The emission assisting layer can improve luminous 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 the flow of electrons from the electron transport region. The emission assisting layer and the electron blocking layer can each independently include any of the materials described above.
[0164] p-dopant
[0165] 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.
[0166] The charge generating material may be, for example, a p-dopant.
[0167] In one or more embodiments, the p-dopant can have a lowest unoccupied molecular orbital (LUMO) energy level of about -3.5 eV or less.
[0168] The p-dopant may include at least one selected from quinone derivatives, metal oxides, and cyano-containing compounds, but embodiments of the present disclosure are not limited thereto.
[0169] For example, the p-dopant may include at least one selected from the following compounds:
[0170] Quinone derivatives, such as tetracyanoquinodimethane (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);
[0171] Metal oxides, such as tungsten oxide and / or molybdenum oxide;
[0172] 1,4,5,8,9,12-Hexaazatriphenylene-hexanitrile (HAT-CN); and
[0173] The compound represented by formula 221,
[0174] However, the embodiments of the present disclosure are not limited thereto:
[0175]
[0176] Formula 221
[0177]
[0178] In formula 221,
[0179] R 221 To R 223 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, wherein R 221 To R223 At least one selected from the group consisting of cyano, -F, -Cl, -Br, -I, C substituted with -F 1 -C 20 Alkyl, C substituted with -Cl 1 -C 20 Alkyl, C substituted with -Br 1 -C 20 Alkyl and C substituted with -I 1 -C 20 At least one substituent selected from the group consisting of:
[0180] Emission layer in the organic layer 150
[0181] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and a blue emission layer. In one or more embodiments, the emission layer may have a stacked structure of two or more layers selected from the red emission layer, the green emission layer, and the blue emission layer, wherein the two or more layers are in contact with each other or separated from each other. In one or more embodiments, the emission layer may include two or more materials selected from red light-emitting materials, green light-emitting materials, and blue light-emitting materials, wherein the two or more materials are mixed with each other in a single layer to emit white light.
[0182] 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.
[0183] The amount of the dopant in the emission layer may be in the range of 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.
[0184] The thickness of the emitter layer can be approximately To about In the range of, for example, about To about When the thickness of the emission layer is within any of these ranges, excellent (or suitable) emission characteristics can be obtained without significantly increasing the driving voltage.
[0185] Subject in the emission layer
[0186] The host may include a compound represented by Formula 301:
[0187] Formula 301
[0188] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ]xb21 .
[0189] In formula 301,
[0190] Ar 301 It can be substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,
[0191] xb11 can be 1, 2 or 3,
[0192] L 301 Can be selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0193] xb1 can be an integer from 0 to 5.
[0194] R 301 It can be selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed 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 ),
[0195] xb21 can be an integer from 1 to 5, and
[0196] Q 301 To Q 303 can be independently selected from C 1 -C 10 Alkyl, 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.
[0197] In one or more embodiments, in Formula 301, Ar 301 Can be selected from:
[0198] naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, naphthacene, peryl, perylenyl, pentaphenyl, indenoanthryl, dibenzofuranyl, and dibenzothiophenyl; and
[0199] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -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 of naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, naphthacene, peryl, peryl, pentaphenyl, indenoanthryl, dibenzofuranyl and dibenzothiophenyl, and
[0200] Q 31 To Q 33 can be independently selected from C 1 -C 10 Alkyl, 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.
[0201] In Formula 301, when xb11 is two or more, two or more Ar 301 Can connect via one-touch.
[0202] In one or more embodiments, the compound represented by Formula 301 may be represented by Formula 301-1 or Formula 301-2:
[0203] Formula 301-1
[0204]
[0205] Formula 301-2
[0206]
[0207] In Formula 301-1 and Formula 301-2,
[0208] A 301 To A 304 can be independently be benzene, naphthalene, phenanthrene, fluoranthene, benzo[9,10]phenanthrene, pyrene, pyridine, pyrimidine, indene, fluorene, spirobifluorene, benzofluorene, dibenzofluorene, indole, carbazole, benzocarbazole, dibenzocarbazole, furan, benzofuran, dibenzofuran, naphthofuran, benzonaphthofuran, dinaphthofuran, thiophene, benzothiophene, dibenzothiophene, naphthiophene, benzonaphthothiophene and dinaphthothiophene,
[0209] X 301 Can be O, S or N-[(L304 ) xb4 -R 304 ],
[0210] R 311 To R 314 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -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 ),
[0211] xb22 and xb23 can each independently be 0, 1 or 2,
[0212] L 301 、xb1、R 301 and Q 31 To Q 33 Same as described above,
[0213] L 302 To L 304 can be independently combined with L 301 The same definition,
[0214] xb2 to xb4 may each independently be the same as defined in conjunction with xb1, and
[0215] R 302 To R 304 can be independently combined with R 301 The definition is the same.
[0216] For example, in Formula 301, Formula 301-1, and Formula 301-2, L 301 To L 304 Can be independently selected from:
[0217] Phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene yl, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridylene, imidazopyrimidylene, and azacarbazolylene; and
[0218] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyridyl azine, pyrimidinyl, pyridazinyl, triazine, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, -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 of phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene, yl, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridylene, imidazopyrimidylene and azacarbazolylene, and
[0219] Q 31 To Q 33 Same as described above.
[0220] In one or more embodiments, in Formula 301, Formula 301-1, and Formula 301-2, R 301 To R 304 Can be independently selected from:
[0221] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and
[0222] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyridyl azine, pyrimidinyl, pyridazinyl, triazine, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, -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 selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl, and
[0223] Q 31 To Q 33 Same as described above.
[0224] In one or more embodiments, the host may include an alkaline earth metal complex. For example, the host may be selected from a Be complex (eg, compound H55), a Mg complex, and a Zn complex.
[0225] In one or more embodiments, 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 the embodiments of the present disclosure are not limited thereto:
[0226]
[0227]
[0228]
[0229] [Phosphorescent Dopant in Emission Layer Included in Organic Layer 150]
[0230] The phosphorescent dopant may include an organometallic complex represented by Formula 401:
[0231] Formula 401
[0232] M(L 401 ) xc1 (L 402 ) xc2
[0233] Formula 402
[0234]
[0235] In equations 401 and 402,
[0236] 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),
[0237] L 401 can be selected from the ligand represented by formula 402, xc1 can be 1, 2 or 3, wherein when xc1 is two or more, two or more L 401 can be the same or different from each other,
[0238] L 402It can be an organic ligand, and xc2 can be an integer from 0 to 4, wherein when xc2 is two or more, two or more L 402 can be the same or different from each other,
[0239] X 401 To X 404 may each independently be nitrogen or carbon,
[0240] X 401 and X 403 Can be connected via single or double bonds, X 402 and X 404 Can be connected via single or double bonds,
[0241] A 401 and A 402 can be independently C 5 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group,
[0242] 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, C 1 -C 20 alkoxy, phenyl, biphenyl, terphenyl or naphthyl,
[0243] X 406 Can be a single bond, O or S,
[0244] R 401 and R 402 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 20 Alkyl, substituted or unsubstituted C 1 -C 20 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed 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, C 1 -C 10 Alkoxy, C 6 -C 20 Aryl and C 1 -C 20 Heteroaryl,
[0245] xc11 and xc12 may each independently be an integer from 0 to 10, and
[0246] The * and *' in formula 402 both represent the binding site with M in formula 401.
[0247] In one or more embodiments, in Formula 402, A 401 and A 402They can all be independently selected from phenyl, naphthyl, fluorenyl, spirobifluorenyl, indenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiophenyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl and dibenzothiophenyl.
[0248] In one or more embodiments, in Formula 402, i) X 401 Can be nitrogen, X 402 It can be carbon, or ii) X 401 and X 402 They may both be nitrogen.
[0249] In one or more embodiments, R in equation 402 401 and R 402 Can be independently selected from:
[0250] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;
[0251] The C groups are substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, phenyl, naphthyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl and norbornenyl. 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;
[0252] Cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl;
[0253] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20at least one selected from the group consisting 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;
[0254] -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
[0255] Q 401 To Q 403 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 alkoxy, phenyl, biphenyl, and naphthyl, but the embodiments of the present disclosure are not limited thereto.
[0256] In one or more embodiments, when xc1 in equation 401 is two or greater, two or more L 401 Two A's 401 It can be optionally connected via X as a linker 407 Connect, or two or more L 401 Two A's 402 It can be optionally connected via X as a linker 408 Connection (eg, see Compound PD1 to Compound PD4 and Compound PD7). 407 and X 408 can be 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, C 1 -C 20 alkoxy, phenyl, biphenyl, terphenyl or naphthyl), but the embodiments of the present disclosure are not limited thereto.
[0257] In formula 401, L 402 It can be a monovalent organic ligand, a divalent organic ligand or a trivalent organic ligand. 402 It can be selected from halogen, diketone (e.g., acetylacetone (compound)), carboxylic acid (e.g., picolinic acid (salt)), -C(=O)-, isonitrile, -CN and phosphorus (e.g., phosphine and / or phosphite (salt)), but the embodiments of the present disclosure are not limited thereto.
[0258] In one or more 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:
[0259]
[0260] Fluorescent dopants in the emitting layer
[0261] The fluorescent dopant may include an arylamine compound or a styrylamine compound.
[0262] The fluorescent dopant may include a compound represented by Formula 501:
[0263] Formula 501
[0264]
[0265] In formula 501,
[0266] Ar 501 It can be substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,
[0267] L 501 To L 503 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0268] xd1 to xd3 may each independently be an integer from 0 to 3,
[0269] R 501 and R 502 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and
[0270] xd4 can be an integer from 1 to 6.
[0271] In one or more embodiments, Ar in Formula 501 501 Can be selected from:
[0272] naphthyl, heptathenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, naphthacene, phenanthrenyl, perylenyl, pentaphenanthrenyl, indenoanthryl, and indenophenanthrenyl; and
[0273] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20at least one selected from the group consisting of alkoxy, phenyl, biphenyl, terphenyl and naphthyl, naphthyl, heptalenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, The following examples include 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33,
[0274] In one or more embodiments, L in Formula 501 501 To L 503 Can be independently selected from:
[0275] Phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene phenylene, ...
[0276] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, a phenylene group, a naphthylene group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracene group, an anthracene group, an fluoranthenyl group, a benzo[9,10]phenanthrenyl group, a pyrenyl group, a fluorenyl group, a phenanthrenyl group, a phenanthrenyl group, a fluoranthrenyl group, a benzo[9,10]phenanthrenyl group, a py ... The compounds include phenylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothiophenylene, and pyridylene.
[0277] In one or more embodiments, R in Formula 501 501 and R 502 Can be independently selected from:
[0278] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, and pyridyl; and
[0279] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl and -Si(Q 31 )(Q 32 )(Q 33 ) is at least one selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophene, and pyridyl, and
[0280] Q 31 To Q 33 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.
[0281] In one or more embodiments, xd4 in equation 501 may be 2, but the embodiments of the present disclosure are not limited thereto.
[0282] For example, the fluorescent dopant may be selected from Compound FD1 to Compound FD22:
[0283]
[0284]
[0285]
[0286] In one or more embodiments, the fluorescent dopant may be selected from the following compounds, but the embodiments of the present disclosure are not limited thereto:
[0287]
[0288] Electron transport region in the organic layer 150
[0289] 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 multilayer structure having a plurality of layers including a plurality of different materials.
[0290] The electron transport region may include at least one selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer, but the embodiments of the present disclosure are not limited thereto.
[0291] 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 sequentially stacked (e.g., laminated) from the emission layer in the order stated. However, embodiments of the structure of the electron transport region are not limited thereto.
[0292] The electron transport region (e.g., 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.
[0293] A "π-electron-poor 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.
[0294] For example, the "π-electron-poor nitrogen-containing ring" may be: i) a 5- to 7-membered heteromonocyclic group having at least one *-N=*' portion; ii) a heteropolycyclic group in which two or more 5- to 7-membered heteromonocyclic groups each having at least one *-N=*' portion are condensed with 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=*' portion is condensed with at least one C5 -C 60 A carbocyclic condensed heteropolycyclic group.
[0295] Examples of π-electron-poor 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.
[0296] For example, the electron transport region may include a compound represented by Formula 601:
[0297] Formula 601
[0298] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .
[0299] In formula 601,
[0300] Ar 601 It can be substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,
[0301] xe11 can be 1, 2 or 3,
[0302] L 601 Can be selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0303] xe1 can be an integer from 0 to 5,
[0304] R 601 Can be selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed 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 ),and
[0305] Q 601 To Q 603 can be independently C 1 -C 10 Alkyl, C 1 -C 10 alkoxy, phenyl, biphenyl, terphenyl or naphthyl, and
[0306] xe21 can be an integer from 1 to 5.
[0307] In one or more embodiments, the number of Ar from xe11 601 and xe21 number of R 601 At least one selected from may include a π-electron-poor nitrogen-containing ring.
[0308] In one or more embodiments, Ar in Formula 601 601 Can be selected from:
[0309] Phenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, naphthacene, phenanthrenyl, peryl, pentaphenanthrenyl, indenoanthryl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and
[0310] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q 31 )(Q 32 )(Q 33 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ) is at least one selected from phenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, naphthyl, phenanthrenyl, peryl, pentaphenanthrenyl, indenoanthryl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl, and
[0311] Q 31 To Q 33 can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.
[0312] When xe11 in Formula 601 is two or greater, two or more Ar 601 Can connect via one-touch.
[0313] In one or more embodiments, Ar in Formula 601 601 It may be anthracene.
[0314] In one or more embodiments, the compound represented by Formula 601 can be represented by Formula 601-1:
[0315] Formula 601-1
[0316]
[0317] In formula 601-1,
[0318] X 614 Can be N or C (R 614 ), X 615 Can be N or C (R 615 ), X 616 Can be N or C (R 616 ), and from X 614 To X 616 At least one of the selected ones may be N,
[0319] L 611 To L 613 can be independently combined with L 601 The same definition,
[0320] xe611 to xe613 can all independently be the same as defined in conjunction with xe1,
[0321] R 611 To R 613 can be independently combined with R 601 are defined identically, and
[0322] R 614 To R 616 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.
[0323] In one or more embodiments, L in equation 601 601 and L in formula 601-1 611 To L 613 Can be independently selected from:
[0324] Phenylene, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene yl, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridylene, imidazopyrimidylene, and azacarbazolylene; and
[0325] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazine at least one selected from the group consisting of phenylene, naphthylene, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl, naphthylene, fluorenylene, spirobifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthrylenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, pyrenylene yl, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene , pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridylene, imidazopyrimidylene and azacarbazolylene,
[0326] However, the embodiments of the present disclosure are not limited thereto.
[0327] In one or more embodiments, in Formula 601 and Formula 601-1, xe1 and xe611 to xe613 may each independently be 0, 1, or 2.
[0328] In one or more embodiments, in Formula 601 and Formula 601-1, R 601 and R 611 To R 613 Can be independently selected from:
[0329] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl , pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl;
[0330] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalide a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a benzo[9,10]phenanthrenyl group, a pyrenyl group, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and
[0331] -S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ),and
[0332] Q 601 and Q 602 Same as described above.
[0333] The electron transport region may include at least one compound selected from compound ET1 to compound ET36, but the embodiments of the present disclosure are not limited thereto:
[0334]
[0335]
[0336]
[0337] In one or more embodiments, the electron transport region may include 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq 3 At least one selected from the group consisting of BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ) and NTAZ:
[0338]
[0339] In one or more embodiments, the electron transport region may include a phosphine oxide compound (e.g., TSPO1 used in the following examples, etc.), but the embodiments of the present disclosure are not limited thereto. In one or more embodiments, a phosphine oxide compound may be used in a hole blocking layer in the electron transport region, but the embodiments of the present disclosure are not limited thereto.
[0340] The thickness of the buffer layer, the hole blocking layer, and the electron control layer can each independently be about To about In the range of, for example, about To about When the thickness of the buffer layer, the hole blocking layer or the electron control layer is within any of these ranges, excellent (or suitable) hole blocking characteristics and / or electron control characteristics can be obtained without significantly increasing the driving voltage.
[0341] The thickness of the electron transport layer can be about To about In the range of, for example, about To about When the thickness of the electron transport layer is within the range described above, satisfactory (or appropriate) electron transport characteristics may be obtained without significantly increasing the driving voltage.
[0342] In addition to the materials described above, the electron transport region (eg, an electron transport layer in the electron transport region) may further include a metal-containing material.
[0343] 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.
[0344] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (lithium hydroxyquinoline, LiQ) and / or compound ET-D2:
[0345]
[0346] The electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 190. The electron injection layer may be in direct contact with the second electrode 190.
[0347] 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 multilayer structure having a plurality of layers including a plurality of different materials.
[0348] 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 one or more combinations thereof.
[0349] 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.
[0350] The alkaline earth metal may be selected from Mg, Ca, Sr and Ba.
[0351] The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb and Gd.
[0352] The alkali metal compound, the alkaline earth metal compound and the rare earth metal compound may be selected from oxides and halides (eg, fluorides, chlorides, bromides and / or iodides) of alkali metals, alkaline earth metals and rare earth metals, respectively.
[0353] The alkali metal compound may be selected from alkali metal oxides (such as, Li 2 O, Cs 2 O and / or K 2 O) and alkali metal halides (such as, 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.
[0354] 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.
[0355] 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.
[0356] The alkali metal complex, alkaline earth metal complex and rare earth metal complex may respectively include ions of the alkali metal, alkaline earth metal and rare earth metal 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.
[0357] The electron injection layer may include alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any one or more combinations thereof as described above (e.g., may be composed of alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any one or more combinations thereof as described above). In one or more embodiments, the electron injection layer may also include organic materials. When the electron injection layer also includes organic materials, alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any one or more combinations thereof may be uniformly or non-uniformly dispersed in a matrix including an organic material.
[0358] The thickness of the electron injection layer can be about To about In the range of, for example, about To about When the thickness of the electron injection layer is within any of the ranges described above, satisfactory (or appropriate) electron injection characteristics can be obtained without significantly increasing the driving voltage.
[0359] The second electrode 190
[0360] The second electrode 190 may be disposed on the organic layer 150 having the structure according to an embodiment of the present disclosure. The second electrode 190 may be a cathode as 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.
[0361] 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.
[0362] The second electrode 190 may have a single-layer structure or a multi-layer structure including two or more layers.
[0363] Figures 2 to 4 Description
[0364] Figure 2is a schematic diagram of an organic light emitting device 20 according to an embodiment. The organic light emitting device 20 includes a first capping layer 210, a first electrode 110, an organic layer 150, and a second electrode 190 which are sequentially stacked (eg, laminated) in the stated order. Figure 3 is a schematic diagram 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 (eg, laminated) in the stated order. Figure 4 is a schematic diagram of an organic light emitting device 40 according to an embodiment. The organic light emitting device 40 includes a first capping layer 210, a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220 sequentially stacked (eg, laminated) in the stated order.
[0365] about Figures 2 to 4 , can be combined by reference Figure 1 Their respective descriptions are given to understand the first electrode 110 , the organic layer 150 , and the second electrode 190 .
[0366] 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.
[0367] The first capping layer 210 and the second capping layer 220 may improve external light emitting efficiency according to the principle of constructive interference.
[0368] 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. The organic capping layer may include polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resin (e.g., polymethyl methacrylate, polyacrylic acid, etc.), or any one or more combinations thereof.
[0369] At least one selected from the first capping layer 210 and the second capping layer 220 may each independently include at least one material selected from carbocyclic compounds, heterocyclic compounds, amine compounds, porphyrin derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, and alkaline earth metal complexes. The carbocyclic compounds, heterocyclic compounds, and amine compounds may each independently and selectively be substituted with a substituent containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I.
[0370] In one or more embodiments, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include an amine compound.
[0371] In one or more embodiments, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include a compound selected from the group consisting of compounds CP1 to CP5, but the embodiments of the present disclosure are not limited thereto:
[0372]
[0373] In the above, it has been combined Figures 1 to 4 The organic light emitting device according to one or more embodiments of the present disclosure is described, but the embodiments of the present disclosure are not limited thereto.
[0374] A layer constituting a hole transport region, an emission layer, and a layer constituting an electron transport region can be formed in a specific region independently by 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.
[0375] When the layer constituting the hole transport region, the emission layer, and / or 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 Up to about 10 -3 Torr vacuum and approx. / second to approximately The vacuum deposition was performed at a deposition rate of 2000 Å / s.
[0376] When a layer constituting a hole transport region, an emission layer and / or a layer constituting an electron transport region is formed by spin coating, spin coating can be performed at a coating speed of about 2000 rpm to about 5000 rpm and at a heat treatment temperature of about 80°C to about 200°C by taking into account the materials to be included in the layer to be formed and the structure of the layer to be formed.
[0377] equipment
[0378] The organic light emitting device may be included in various suitable devices. For example, a light emitting device, an authentication device, and / or an electronic device including the organic light emitting device may be provided.
[0379] In addition to the organic light-emitting device, the light-emitting device may further include a thin film transistor including a source electrode and a drain electrode. One of the source electrode and the drain electrode of the thin film transistor may be electrically connected to one of the first electrode and the second electrode of the organic light-emitting device. The light-emitting device may be used as various suitable displays and / or light sources, etc.
[0380] The authentication device may be, for example, a biometric authentication device for authenticating an individual by using biometric information of a biometric body (eg, fingertips and / or pupils, etc.).
[0381] In addition to the organic light emitting device, the authentication device may also include a biometric information collector.
[0382] The electronic device can be applied to personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notepads, electronic dictionaries, electronic game consoles, medical equipment (e.g., electronic thermometers, sphygmomanometers, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram (ECG) displays, ultrasonic diagnostic devices and / or endoscopic displays), fish finders, various measuring instruments, meters (e.g., meters for vehicles, aircraft and / or ships) and / or projectors, etc., but the embodiments of the present disclosure are not limited thereto.
[0383] General Definition of Substituents
[0384] As used herein, the term "C 1 -C 60 The term “alkyl” may refer to a linear or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms, and non-limiting examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl.
[0385] As used herein, the term "C 2 -C 60 "Alkenyl" may refer to 2 -C 60 The hydrocarbon chain of the alkyl group is substituted at one or more positions (e.g., at C 2 -C 60 The hydrocarbon group may be a hydrocarbon group having at least one carbon-carbon double bond (in the middle and / or at the terminal of the alkyl group), non-limiting examples of which include ethenyl, propenyl, and butenyl.
[0386] As used herein, the term "C 2 -C 60 "Alkynyl" may refer to2 -C 60 The hydrocarbon chain of the alkyl group is substituted at one or more positions (e.g., at C 2 -C 60 The terminator may be a hydrocarbon group having at least one carbon-carbon triple bond (in the middle and / or at the terminal of the alkyl group), non-limiting examples of which include ethynyl and propynyl.
[0387] As used herein, the term "C 1 -C 60 "Alkoxy" may refer to -OA 101 (Among them, A 101 C 1 -C 60 The monovalent group represented by an alkyl group is a methoxy group, an ethoxy group, and an isopropoxy group.
[0388] As used herein, the term "C 3 -C 10 "Cycloalkyl" may refer to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, non-limiting examples of which include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. As used herein, the term "Cycloalkyl" may refer to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, non-limiting examples of which include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. 3 -C 10 "Cycloalkylene" may refer to 3 -C 10 The cycloalkyl group is a divalent group having the same structure.
[0389] As used herein, the term "C 1 -C 10 The term “heterocycloalkyl” as used herein may refer to a monovalent saturated monocyclic group having at least one heteroatom 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 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl and tetrahydrothienyl. 1 -C 10 "Heterocycloalkylene" may refer to 1 -C 10 The heterocycloalkyl group has a divalent group of the same structure.
[0390] As used herein, the term “C 3 -C 10 "Cycloalkenyl" 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 not having aromaticity, and non-limiting examples thereof include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "Cycloalkenyl" 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 not having aromaticity, and non-limiting examples thereof include cyclopentenyl, cyclohexenyl, and cycloheptenyl. 3 -C 10 "Cycloalkenylene" may refer to 3 -C 10 The cycloalkenyl group is a divalent group having the same structure.
[0391] As used herein, the term "C 1 -C 10 The term "heterocycloalkenyl group" may refer to a monovalent monocyclic group having at least one hetero atom selected from N, O, Si, P and S as ring-forming atoms, 1 to 10 carbon atoms and at least one double bond in its ring. 1 -C 10 Non-limiting examples of heterocycloalkenyl groups include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothienyl. As used herein, the term “C 1 -C 10 "Heterocycloalkenylene" may refer to 1 -C 10 The heterocycloalkenyl group is a divalent group having the same structure.
[0392] As used herein, the term "C 6 -C 60 The term "aryl" may refer to a monovalent group having a carbocyclic aromatic system including 6 to 60 carbon atoms. 6 -C 60 Non-limiting examples of aryl groups include phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, and As used herein, the term "C 6 -C 60 "Arylene" may refer to 6 -C 60 Aryl has the same structure as a divalent group. 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each independently include two or more rings, the respective rings may be fused (condensed) to each other.
[0393] As used herein, the term "C 1 -C 60 The term "heteroaryl group" may refer to a monovalent group having a heterocyclic aromatic system having at least one hetero atom selected from N, O, Si, P and S as a ring-forming atom in addition to 1 to 60 carbon atoms. 1 -C 60 Non-limiting examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. As used herein, the term “C 1 -C 60 "Heteroarylene" may refer to 1 -C 60 Heteroaryl has a divalent group with the same structure. 1 -C 60 Heteroaryl and C 1 -C60 When the heteroarylene groups each independently include two or more rings, the respective rings may be condensed (fused) to each other.
[0394] As used herein, the term "C 6 -C 60 "Aryloxy" may refer to -OA 102 (Among them, A 102 C 6 -C 60 The term "C 6 -C 60 "Arylthio" may refer to -SA 103 (Among them, A 103 C 6 -C 60 A monovalent group represented by an aryl group.
[0395] The term "monovalent non-aromatic condensed polycyclic group" as used herein may refer to a monovalent group having two or more rings condensed with each other, only carbon atoms (e.g., having 8 to 60 carbon atoms) as ring atoms, and not having aromaticity in its entire molecular structure. A non-limiting example of a monovalent non-aromatic condensed polycyclic group is a fluorenyl group. The term "divalent non-aromatic condensed polycyclic group" as used herein may refer to a divalent group having the same structure as a monovalent non-aromatic condensed polycyclic group.
[0396] The term "monovalent non-aromatic condensed heteropolycyclic group" as used herein may refer to a monovalent group having two or more rings condensed with each other, at least one heteroatom selected from N, O, Si, P and S as ring-forming atoms other than carbon atoms (e.g., having 1 to 60 carbon atoms), and not having aromaticity in its entire molecular structure. A non-limiting example of a monovalent non-aromatic condensed heteropolycyclic group is a carbazolyl group. The term "divalent non-aromatic condensed heteropolycyclic group" as used herein may refer to a divalent group having the same structure as a monovalent non-aromatic condensed heteropolycyclic group.
[0397] As used herein, the term "C 5 -C 60 "Carbocyclic group" may refer to a monocyclic or polycyclic group having 5 to 60 carbon atoms, wherein the ring atoms are only carbon atoms. As used herein, the term "C 5 -C 60 "Carbocyclic group" may refer to an aromatic carbocyclic group or a non-aromatic carbocyclic group. 5 -C 60 The carbocyclic group can be a ring (such as benzene), a monovalent group (such as phenyl) or a divalent group (such as phenylene). In one or more embodiments, the carbonyl group is connected to the carbonyl group. 5 -C 60 The number of substituents of the carbocyclic group, C5 -C 60 The carbocyclic group may be a trivalent group or a tetravalent group.
[0398] As used herein, the term "C 1 -C 60 The term "heterocyclic group" may refer to a group consisting of at least one heteroatom selected from N, O, Si, P and S other than carbon atoms (the number of carbon atoms may be in the range of 1 to 60) as a ring-forming atom. 5 -C 60 The carbocyclic group has a group of the same structure.
[0399] In this specification, substituted C 5 -C 60 Carbocyclic, substituted C 1 -C 60 Heterocyclic, substituted C 3 -C 10 Cycloalkylene, substituted C 1 -C 10 Heterocycloalkylene, substituted C 3 -C 10 Cycloalkenylene, substituted C 1 -C 10 Heterocycloalkenylene, substituted C 6 -C 60 Arylene, substituted C 1 -C 60 Heteroarylene, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60At least one substituent in the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:
[0400] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;
[0401] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed 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 ) selected from at least one of the C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;
[0402] C 3 -C 10Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups;
[0403] are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed 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 ) selected from at least one of the C 3 -C 10Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and
[0404] -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
[0405] 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, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, C substituted with at least one selected from deuterium, -F and cyano 1 -C 60 alkyl, C substituted with at least one selected from deuterium, -F and cyano 6 -C 60 Aryl, biphenyl and terphenyl.
[0406] 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, and the terms "ter-Bu" or "Bu" as used herein may refer to a phenyl group. t " may refer to tert-butyl, the term "OMe" as used herein may refer to methoxy, and "D" may refer to deuterium.
[0407] As used herein, the term "biphenyl" may refer to a "phenyl group substituted with a phenyl group". For example, a "biphenyl group" may be a group having C 6 -C 60 A phenyl group substituted with an aryl group as a substituent.
[0408] As used herein, the term "terphenyl" may refer to a "phenyl group substituted with a biphenyl group". For example, a "terphenyl group" may be a phenyl group substituted with a C 6 -C 60 Aryl C 6 -C 60 Phenyl with aryl as substituent.
[0409] Unless otherwise defined, * and *' used herein refer to the binding sites to adjacent atoms in the corresponding formula.
[0410] 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 expression "using B instead of A" used in describing Synthesis Examples may mean using B instead of A with the same molar equivalent.
[0411] Example
[0412] Synthesis Example: Synthesis of a Compound
[0413] Synthesis Example 1: Synthesis of Compound 1
[0414]
[0415] Synthesis of intermediate 1-1
[0416] 2.59 g (10 mmol) of 9-phenyl-9H-carbazole-2-ol was dissolved in 20 mL of dichloromethane (DCM), and N-bromosuccinimide (1.78 g in DCM) was added thereto at 0° C. The reaction solution was stirred at room temperature for 5 hours, and 3 g of Na 2 S 2 O 3 Dissolved in water and added to the reaction solution. The resulting solution was washed 3 times with DCM (30 mL). 4 The washed DCM layer was dried and evaporated under reduced pressure to obtain the product. The product was separated and purified by silica gel chromatography to obtain 2.70 g of Intermediate 1-1 (white solid) (yield 80%). The obtained compound was identified by LC-MS (liquid chromatography-mass spectrometry). 18 H 12 BrNO:M + 338.2.
[0417] Synthesis of intermediate 1-2
[0418] 3.38 g (10 mmol) of intermediate 1-1, 1.69 g (10 mmol) of diphenylamine, 0.46 g (0.5 mmol) of Pd 2 dba 3 (Tris(dibenzylideneacetone)dipalladium(0)) and 2.88 g (30 mmol) of sodium tert-butoxide were dissolved in 60 mL of toluene and stirred at 80° C. for 3 hours. The reaction solution was cooled to room temperature, 40 mL of water was added thereto, and the organic layer was extracted therefrom three times by 50 mL of diethyl ether. The reaction mixture was stirred for 3 hours using MgSO 4 The collected organic layer was dried, and the residue obtained by evaporating the solvent therefrom was separated and purified by silica gel chromatography to obtain 3.20 g of Intermediate 1-2 (yield 75%). The obtained compound was identified by LC-MS. 30 H 22 N 2 O:M + 426.5.
[0419] Synthesis of intermediate 1-3
[0420] 2.29 g of p-toluenesulfonyl chloride (TsCl) was dissolved in 20 mL of DCM, slowly added to a flask in which 4.27 g (10 mmol) of intermediate 1-2 and 4.18 mL (30 mmol) of triethylamine were dissolved in 60 mL of DCM at a temperature of 0° C., and then stirred at room temperature for 5 hours. 40 mL of water was added to the reaction solution, and an organic layer was extracted therefrom three times by using 50 mL of diethyl ether. The reaction mixture was stirred for 5 hours by using MgSO 4 The collected organic layer was dried, and the residue obtained by evaporating the solvent therefrom was separated and purified by silica gel chromatography to obtain 4.64 g of Intermediate 1-3 (yield 80%). The obtained compound was identified by LC-MS. 37 H 28 N 2 O 3 S:M + 580.7.
[0421] Synthesis of compound 1
[0422] 5.81 g (10.0 mmol) of intermediate 1-3, 1.46 g (12.0 mmol) of phenylboronic acid, 0.58 g (0.5 mmol) of Pd(PPh 3 ) 4 and 4.14 g (30.0 mmol) of K 2 CO 3 Dissolve in 60 mL of THF / H 2 O (2 / 1) mixed solution, and stirred at a temperature of 80 ° C for 16 hours. The reaction solution was cooled to room temperature, and an organic layer was extracted therefrom three times by using 60 mL of water and 60 mL of diethyl ether. The organic layer obtained therefrom was dried by using magnesium sulfate, and the residue obtained by evaporating the solvent therefrom was separated and purified by silica gel chromatography to obtain 3.40 g of compound 1 (yield 70%). By MS / FAB (mass spectrometry / fast atom bombardment) and 1 The obtained compound was confirmed by H NMR. 36 H 26 N 2 :M + Calculated value: 486.62, found value 486.52.
[0423] Synthesis Example 2: Synthesis of Compound 2
[0424]
[0425] Compound 2 was synthesized in the same (or substantially the same) manner as Compound 1, except that N-phenyl-[1,1'-biphenyl]-4-amine was used instead of diphenylamine. 1 The obtained compound was confirmed by H NMR. 42 H 30 N 2 :M + Calculated value: 562.24, found value 562.14.
[0426] Synthesis Example 3: Synthesis of Compound 6
[0427]
[0428] Compound 6 was synthesized in the same (or substantially the same) manner as Compound 1, except that N-phenylnaphthalene-2-amine was used instead of diphenylamine. 1 The obtained compound was confirmed by H NMR. 40 H 28 N 2 :M + Calculated: 536.23, found: 536.13.
[0429] Synthesis Example 4: Synthesis of Compound 10
[0430]
[0431] Compound 10 was synthesized in the same (or substantially the same) manner as Compound 1, except that N-phenyldibenzo[b,d]furan-2-amine was used instead of diphenylamine. 1 The obtained compound was confirmed by H NMR. 42 H 28 N 2 O:M + Calculated value: 576.70, found value 576.60.
[0432] Synthesis Example 5: Synthesis of Compound 33
[0433]
[0434] Synthesis of Intermediate 33-1
[0435] 3.38 g (10.0 mmol) of intermediate 1-1, 1.56 g (10.0 mmol) of (4-chlorophenyl)boronic acid, 0.58 g (0.5 mmol) of Pd(PPh 3 ) 4 and 4.14 g (30.0 mmol) of K 2 CO3 Dissolve in 60 mL of THF / H 2 O (2 / 1) mixed solution, and stirred at a temperature of 80 ° C for 16 hours. The reaction solution was cooled to room temperature, and an organic layer was extracted therefrom three times by using 60 mL of water and 60 mL of diethyl ether. The organic layer obtained therefrom was dried by using magnesium sulfate, and the residue obtained by evaporating the solvent therefrom was separated and purified by silica gel chromatography to obtain 2.59 g of intermediate 33-1 (yield 70%). The obtained compound was determined by LC-MS. C 24 H 16 ClNO:M + 369.0.
[0436] Synthesis of Intermediate 33-2
[0437] 3.70 g (10 mmol) of intermediate 33-1, 1.69 g (10 mmol) of diphenylamine, 0.46 g (0.5 mmol) of Pd 2 dba 3 (Tris(dibenzylideneacetone)dipalladium(0)) and 2.88 g (30 mmol) of sodium tert-butoxide were dissolved in 60 mL of toluene and stirred at 80° C. for 3 hours. The reaction solution was cooled to room temperature, 40 mL of water was added thereto, and an organic layer was extracted therefrom three times by using 50 mL of diethyl ether. The mixture was stirred for 3 hours by using MgSO 4 The collected organic layer was dried, and the residue obtained by evaporating the solvent therefrom was separated and purified by silica gel chromatography to obtain 3.52 g of Intermediate 33-2 (yield 70%). The obtained compound was identified by LC-MS. 36 H 26 N 2 O:M + 502.2.
[0438] Synthesis of intermediate 33-3
[0439] 2.29 g of p-toluenesulfonyl chloride (TsCl) was dissolved in 20 mL of DCM, slowly added to a flask in which 5.03 g (10 mmol) of intermediate 33-2 and 4.18 mL (30 mmol) of triethylamine were dissolved in 60 mL of DCM at a temperature of 0° C., and then stirred at room temperature for 5 hours. 40 mL of water was added to the reaction solution, and an organic layer was extracted therefrom three times by using 50 mL of diethyl ether. The mixture was stirred for 5 hours by using MgSO 4The collected organic layer was dried, and the residue obtained by evaporating the solvent therefrom was separated and purified by silica gel chromatography to obtain 5.26 g of Intermediate 33-3 (yield 80%). The obtained compound was identified by LC-MS. 43 H 32 N 2 O 3 S:M + 656.2.
[0440] Synthesis of compound 33
[0441] 6.57 g (10.0 mmol) of intermediate 33-3, 1.46 g (12.0 mmol) of phenylboronic acid, 0.58 g (0.5 mmol) of Pd(PPh 3 ) 4 and 4.14 g (30.0 mmol) of K 2 CO 3 Dissolve in 60 mL of THF / H 2 O (2 / 1) mixed solution, and stirred at a temperature of 80 ° C for 16 hours. The reaction solution was cooled to room temperature, and an organic layer was extracted therefrom three times by using 60 mL of water and 60 mL of diethyl ether. The organic layer obtained therefrom was dried using magnesium sulfate, and the residue obtained by evaporating the solvent therefrom was separated and purified by silica gel chromatography to obtain 3.94 g of compound 33 (yield 70%). By MS / FAB and 1 The obtained compound was confirmed by H NMR. 42 H 30 N 2 :M + Calculated value: 562.24, found value 562.14.
[0442] Synthesis Example 6: Synthesis of Compound 34
[0443]
[0444] Compound 34 was synthesized in the same (or substantially the same) manner as Compound 33, except that N-phenyl-[1,1'-biphenyl]-4-amine was used instead of diphenylamine. 1 The obtained compound was confirmed by H NMR. 48 H 34 N 2 :M + Calculated value: 638.27, found value 638.17.
[0445] Synthesis Example 7: Synthesis of Compound 38
[0446]
[0447] Compound 38 was synthesized in the same (or substantially the same) manner as Compound 33, except that N-phenylnaphthalene-2-amine was used instead of diphenylamine. 1 The obtained compound was confirmed by H NMR. 46 H 32 N 2 :M + Calculated value: 612.26, found value 612.16.
[0448] Synthesis Example 8: Synthesis of Compound 42
[0449]
[0450] Compound 42 was synthesized in the same (or substantially the same) manner as Compound 33, except that N-phenyldibenzo[b,d]furan-2-amine was used instead of diphenylamine. 1 The obtained compound was confirmed by H NMR. 48 H 32 N 2 O:M + Calculated value: 652.25, found value 652.15.
[0451] The compounds synthesized in the synthesis examples 1 H NMR and MS / FAB are shown in Table 1.
[0452] The synthesis methods of compounds other than those shown in Table 1 should be apparent to those of ordinary skill in the art by referring to the above-described synthesis mechanisms and starting materials.
[0453] Table 1
[0454]
[0455]
[0456] Fabrication of organic light-emitting devices
[0457] Comparative Example 1
[0458] Corning 15Ω / cm 2 The ITO glass substrate was cut into a size of 50 mm×50 mm×0.7 mm, ultrasonicated using 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.
[0459] 2-TNATA was vacuum deposited on an ITO glass substrate to form A hole injection layer having a thickness of , and a hole transport material 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) is vacuum deposited on the hole injection layer to form a The hole transport layer has a thickness of .
[0460] A blue fluorescent host 9,10-di(naphthalene-2-yl)anthracene (DNA) and a blue fluorescent dopant 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi) were co-deposited on the hole transport layer in a weight ratio of 98:2 to form a blue fluorescent dopant having The thickness of the emission layer.
[0461] Comparative Example 2
[0462] An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Comparative Compound 638 was used instead of NPB in forming the hole transport layer.
[0463]
[0464] Comparative Compound 638
[0465] Comparison Example 3
[0466] An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Comparative Compound 31 was used instead of NPB in forming the hole transport layer.
[0467]
[0468] Comparative Compound 31
[0469] Comparison Example 4
[0470] An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Comparative Compound 3-22-1 was used instead of NPB in forming the hole transport layer.
[0471]
[0472] Comparative compound 3-22-1
[0473] Example 1
[0474] An organic light emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 1 was used instead of NPB in forming the hole transport layer.
[0475] Example 2
[0476] An organic light emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 2 was used instead of NPB in forming the hole transport layer.
[0477] Example 3
[0478] An organic light emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 6 was used instead of NPB in forming the hole transport layer.
[0479] Example 4
[0480] An organic light emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 10 was used instead of NPB in forming the hole transport layer.
[0481] Example 5
[0482] An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 33 was used instead of NPB in forming the hole transport layer.
[0483] Example 6
[0484] An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 34 was used instead of NPB in forming the hole transport layer.
[0485] Example 7
[0486] An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 38 was used instead of NPB in forming the hole transport layer.
[0487] Example 8
[0488] An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 42 was used instead of NPB in forming the hole transport layer.
[0489] The driving voltage, luminance, efficiency, and lifespan of the organic light emitting devices manufactured according to Examples 1 to 8 and Comparative Examples 1 to 4 were measured, and the results are shown in Table 2.
[0490] Table 2
[0491]
[0492]
[0493] Referring to Table 2, it was confirmed that the organic light emitting devices of Examples 1 to 8 showed excellent results including lower driving voltage and higher brightness, efficiency, and half-life compared to the organic light emitting devices of Comparative Examples 1 to 4.
[0494] An organic light emitting device including the compound represented by Formula 1 may have excellent efficiency.
[0495] As used herein, the term "use" and variations thereof may be considered synonymous with the term "utilize" and variations thereof, respectively.
[0496] Additionally, the terms "substantially," "approximately," 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 having ordinary skill in the art.
[0497] In addition, any numerical range stated herein is intended to include all subranges of the same numerical precision contained in the stated range. For example, the range "1.0 to 10.0" is intended to include all subranges between the stated minimum value 1.0 and the stated maximum value 10.0 (and including the stated minimum value 1.0 and the stated maximum value 10.0), 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 limit stated herein is intended to include all lower numerical limits contained therein, and any minimum numerical limit stated in this specification is intended to include all higher numerical limits contained therein. Therefore, the applicant reserves the right to modify this specification (including claims) to explicitly state any subrange contained in the scope explicitly stated herein.
[0498] 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.
[0499] Although one or more embodiments have been described with reference to the 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: first cap layer; A first electrode, located on the first cover layer; a second electrode, facing the first electrode; an organic layer, located between the first electrode and the second electrode, the organic layer comprising an emission layer; and a second capping layer, located on the second electrode, in: The organic layer includes a carbazole derivative represented by Formula 1: Formula 1 Among them, in formula 1, R1 and R4 to R8 are each independently hydrogen or deuterium, R2 and Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, R9 is selected from substituted or unsubstituted C6-C 60 Aryl, L is selected from a single bond, a substituted or unsubstituted C6-C 60 Arylene, substituted or unsubstituted C1-C 60 heteroarylene, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group, The substituted C6-C 60 Aryl, the substituted C1-C 60 heteroaryl, the substituted monovalent non-aromatic condensed polycyclic group, the substituted monovalent non-aromatic condensed heteropolycyclic group, the substituted C6-C 60 Arylene, the substituted C1-C 60 At least one substituent in the heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group and the substituted divalent non-aromatic condensed heteropolycyclic group is selected from: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 Alkoxy; are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed 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 ) selected from at least one of C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 Alkoxy; C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups; are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed 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 ) selected from at least one of C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed 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 Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C1-C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, monovalent non-aromatic condensed heteropolycyclic groups, biphenyl groups and terphenyl groups.
2. The organic light emitting device according to claim 1, wherein: R9 in Formula 1 is represented by Formula 2a: Wherein, in Formula 2a, R 11 Selected from hydrogen, deuterium, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) and -P(=O)(Q1)(Q2), a11 is an integer from 1 to 4, The substituted C1-C 60 Alkyl, the substituted C2-C 60 Alkenyl, the substituted C2-C 60 Alkynyl, the substituted C1-C 60 Alkoxy, the substituted C3-C 10 Cycloalkyl, the substituted C1-C 10 Heterocycloalkyl, the substituted C3-C 10 Cycloalkenyl, the substituted C1-C 10 Heterocycloalkenyl, the substituted C6-C 60 Aryl, the substituted C6-C 60 Aryloxy, the substituted C6-C 60 Arylthio, the substituted C1-C 60 At least one substituent in the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from: Deuterium, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 Alkoxy; All are substituted with deuterium, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -O(Q 11 )、-S(Q 11 )、-Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-P(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 ) and -P(=O)(Q 11 )(Q 12 ) selected from at least one of C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 Alkoxy; C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups; All are substituted with deuterium, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -O(Q 21 )、-S(Q 21 )、-Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-P(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 ) and -P(=O)(Q 21 )(Q 22 ) selected from at least one of C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 )和-P(=O)(Q 31 )(Q 32 ), Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are independently selected from hydrogen, deuterium, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C1-C 60 A heteroaryl group, a monovalent nonaromatic condensed polycyclic group, a monovalent nonaromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, and * represents a bonding position with an adjacent atom.
3. The organic light emitting device according to claim 1, wherein: R2 in Formula 1 is represented by one selected from Formula 3a to Formula 3c: Wherein, in Formula 3a to Formula 3c, R 21 To R 23 are independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) and -P(=O)(Q1)(Q2), X1 is O, S or CR 51 R 52 , R 51 and R 52 are independently selected from substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C6-C 60 Aryl and substituted or unsubstituted C1-C 60 Heteroaryl, a21 is an integer from 1 to 4, a22 and a23 are each independently an integer from 1 to 6, The substituted C1-C 60 Alkyl, the substituted C2-C 60 Alkenyl, the substituted C2-C 60 Alkynyl, the substituted C1-C 60 Alkoxy, the substituted C3-C 10 Cycloalkyl, the substituted C1-C 10 Heterocycloalkyl, the substituted C3-C 10 Cycloalkenyl, the substituted C1-C 10 Heterocycloalkenyl, the substituted C6-C 60 Aryl, the substituted C6-C 60 Aryloxy, the substituted C6-C 60 Arylthio, the substituted C1-C 60 At least one substituent in the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from: Deuterium, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 Alkoxy; All are substituted with deuterium, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -O(Q 11 )、-S(Q 11 )、-Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-P(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 ) and -P(=O)(Q 11 )(Q 12 ) selected from at least one of C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 Alkoxy; C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups; All are substituted with deuterium, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -O(Q 21 )、-S(Q 21 )、-Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-P(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 ) and -P(=O)(Q 21 )(Q 22 ) selected from at least one of C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 )和-P(=O)(Q 31 )(Q 32 ), Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are independently selected from hydrogen, deuterium, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C1-C 60 A heteroaryl group, a monovalent nonaromatic condensed polycyclic group, a monovalent nonaromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, and * represents a bonding position with an adjacent atom.
4. The organic light emitting device according to claim 1, wherein: Ar1 and Ar2 in Formula 1 are each independently represented by one selected from Formula 4a to Formula 4d: Wherein, in Formula 4a to Formula 4d, R 31 To R 34 are independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) and -P(=O)(Q1)(Q2), X2 is O, S or CR 53 R 54 , R 53 and R 54 are independently selected from substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C6-C 60 Aryl and substituted or unsubstituted C1-C 60 Heteroaryl, a31 is an integer from 1 to 4, a32 and a34 are each independently an integer from 1 to 6, a33 is an integer from 1 to 8, The substituted C1-C 60 Alkyl, the substituted C2-C 60 Alkenyl, the substituted C2-C 60 Alkynyl, the substituted C1-C 60 Alkoxy, the substituted C3-C 10 Cycloalkyl, the substituted C1-C 10 Heterocycloalkyl, the substituted C3-C 10 Cycloalkenyl, the substituted C1-C 10 Heterocycloalkenyl, the substituted C6-C 60 Aryl, the substituted C6-C 60 Aryloxy, the substituted C6-C 60 Arylthio, the substituted C1-C 60 At least one substituent in the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 Alkoxy; are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -O(Q 11 )、-S(Q 11 )、-Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-P(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 ) and -P(=O)(Q 11 )(Q 12 ) selected from at least one of C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl and C1-C 60 Alkoxy; C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups; are substituted with deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -O(Q 21 )、-S(Q 21 )、-Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-P(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 ) and -P(=O)(Q 21 )(Q 22 ) selected from at least one of C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ), Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C1-C 60 heteroaryl, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group, and *Indicates the binding site with the adjacent atom.
5. The organic light emitting device according to claim 1, wherein: L in Formula 1 is a single bond or a group represented by Formula 5a: In Formula 5a, * represents the bonding site with the adjacent atom.
6. The organic light emitting device according to claim 1, wherein: The carbazole derivative represented by Formula 1 is selected from Compound 1 to Compound 84:
7. The organic light emitting device according to claim 1, wherein: The first electrode is an anode, The second electrode is a cathode, and The organic layer further comprises: i) a hole transport region, located between the first electrode and the emission layer, the hole transport region comprising a hole injection layer, a hole transport layer, a buffer layer, an electron blocking layer or any combination thereof; and ii) an electron transport region, located between the emission layer and the second electrode, wherein the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer or any combination thereof.
8. 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 further comprises: i) a hole transport region, located between the first electrode and the emission layer, the hole transport region comprising a hole injection layer, a hole transport layer, a buffer layer, an electron blocking layer or any combination thereof; and ii) an electron transport region located between the emissive layer and the second electrode, the electron transport region comprising a hole blocking layer, an electron transport layer, an electron injection layer or any combination thereof, and The hole transport region includes the carbazole derivative.
9. A compound selected from the following compounds:
