Organic Light Emitting Device
By optimizing the design of the organic layer and combining specific organic compounds and electrode structures, the shortcomings of existing organic light emitting devices in brightness and driving voltage are solved, and an efficient and simplified organic light emitting device is achieved, with wide viewing angle, high contrast and short response. Characteristics of time.
Patent Information
- Application Number
- CN202011545665.2
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2015-12-29
- Filing Date
- 2016-10-31
- Publication Date
- 2025-01-07
- Estimated Expiration
- 2036-10-31
AI Technical Summary
While achieving wide viewing angle, high contrast and short response time, existing organic light emitting devices are difficult to take into account excellent brightness and driving voltage characteristics, and the structure is complex and manufacturing is difficult.
Using an organic layer composed of specific organic compounds, including a light emitting layer, the carrier recombination efficiency and light generation ability are improved and the structure is simplified by optimizing the design of the first electrode, the hole transport region and the electron transport region.
An organic light emitting device with high brightness, low driving voltage and short response time is realized, which simplifies the manufacturing process and improves the reliability and efficiency of the equipment.
Smart Images

Figure CN112670425B_ABST
Abstract
Description
[0001] This application is a divisional application of the invention patent application with the application date of October 31, 2016, application number 201610985019.5, and invention name “Organic Light-Emitting Device”.
[0002] CROSS-REFERENCE TO RELATED APPLICATIONS
[0003] This application claims priority to and the benefit of Korean Patent Application No. 10-2015-0188914 filed on December 29, 2015, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Background Art
[0004] 1. Field
[0005] One or more aspects of embodiments of the present disclosure relate to an organic light-emitting device.
[0006] 2. Description of Related Technology
[0007] Organic light-emitting devices are self-luminous devices that have wide viewing angles, high contrast, short response times, and excellent brightness, driving voltage, and response speed characteristics, and can produce full-color images.
[0008] The organic light-emitting device may include a first electrode arranged (e.g., placed) on a substrate, and a hole transport region, a light-emitting layer, an electron transport region, and a second electrode sequentially arranged on the first electrode. Holes provided by, for example, the first electrode may move toward the light-emitting layer through the hole transport region, and electrons provided by, for example, the second electrode may move toward the light-emitting layer through the electron transport region. Then, carriers such as holes and electrons may recombine in the light-emitting layer to generate excitons. These excitons transition from an excited state to a ground state, thereby generating light. Summary of the invention
[0009] One or more aspects of embodiments of the present disclosure relate to an organic light-emitting device.
[0010] Additional aspects will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the embodiments of the invention.
[0011] According to one or more embodiments, an organic light-emitting device includes a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, the organic layer including a light-emitting layer,
[0012] wherein the organic layer comprises a first compound represented by Formula 1 and a second compound represented by Formula 2, excluding the case where the first compound is 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP):
[0013] Formula 1
[0014]
[0015] Formula 2
[0016]
[0017] Among them, in formula 1,
[0018] Ar 11 is a group represented by formula 1-1,
[0019] Formula 1-1
[0020]
[0021] R 11 and R 12 Each is independently selected from the group represented by Formula 8-1, the group represented by Formula 8-2, hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, nitro, substituted or unsubstituted C 1 -C 60 Alkyl, 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, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ),
[0022]
[0023] L 11 To L 12 Each independently selected from *-O-*', *-S-*', *-C(=O)-*', *-P(=O)(Q 1 )-*'、*-Si(Q 1 )(Q 2 )-*', substituted or unsubstituted C 6 -C 60 Arylene and substituted or unsubstituted C 1 -C 60 Heteroarylene,
[0024] m11 is selected from 1 and 2,
[0025] a11 and a12 are each independently selected from 0, 1, 2 and 3,
[0026] n11 and n12 are each independently selected from 0, 1, 2, 3 and 4,
[0027] In Formula 1-1 and Formulas 8-1 to 8-2,
[0028] A 11 , A 12 , A 81 and A 82 Each independently selected from C 5 -C 20 Carbocyclic groups and C 1 -C 20 Heterocyclic groups,
[0029] X 11 Selected from N[(L 13 ) a13 -R 13 ]、C[(L 13 ) a13 -R 13 ][(L 14 ) a14 -R 14 ], O and S,
[0030] X 12 Selected from single bonds, N[(L 15 ) a15 -R 15 ]、C[(L 15 ) a15 -R 15 ][(L 16 ) a16 -R 16 ], O and S,
[0031] R 13 To R 16Each is independently selected from the group represented by Formula 8-1, the group represented by Formula 8-2, hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, nitro, substituted or unsubstituted C 1 -C 60 Alkyl, 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, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ), where R 13 and R 14 are optionally linked to each other to form a ring and R 15 and R 16 are optionally linked to each other to form a ring,
[0032] L 13 To L 16 Each independently selected from *-O-*', *-S-*', *-C(=O)-*', *-P(=O)(Q 1 )-*'、*-Si(Q 1 )(Q 2 )-*', substituted or unsubstituted C 6 -C 60 Arylene and substituted or unsubstituted C 1 -C 60 heteroarylene, a13 to a16 are each independently selected from 0, 1, 2 and 3,
[0033] R 101 and R 102 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, nitro, substituted or unsubstituted C 1 -C 60 Alkyl, 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, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ), b101 and b102 are each independently selected from 1, 2, 3, 4, 5 and 6,
[0034] X 81 Selected from N[(L 81 ) a81 -R 81 ]、C[(L 81 ) a81 -R 81 ][(L 82 ) a82 -R 82 ], O and S,
[0035] X 82 Selected from single bonds, N[(L 83 ) a83 -R 83 ]、C[(L83 ) a83 -R 83 ][(L 84 ) a84 -R 84 ], O and S,
[0036] R 85 and R 86 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, nitro, substituted or unsubstituted C 1 -C 60 Alkyl, 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, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ),
[0037] b85 and b86 are each independently selected from 1, 2, 3, 4, 5 and 6,
[0038] Among them, R 81 To R 84 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, nitro, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 1 -C 60Alkoxy, 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, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ), where R 81 and R 82 are optionally linked to each other to form a ring and R 83 and R 84 are optionally linked to each other to form a ring, wherein Q 1 To Q 3 are each 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,
[0039] L 81 To L 84 Each independently selected from *-O-*', *-S-*', *-C(=O)-*', *-P(=O)(Q 1 )-*'、*-Si(Q 1 )(Q 2 )-*', substituted or unsubstituted C 6 -C 60 Arylene and substituted or unsubstituted C 1 -C 60 heteroarylene, a81 to a84 are each independently selected from 0, 1, 2 and 3,
[0040] In formula 2,
[0041] A 21 Selected from C 6 -C 20 Aromatic groups and C 1 -C 20 Heteroaromatic groups,
[0042] X 21 Selected from N and C (R 21 ), X 22 Selected from N and C (R 22 ), X 23 Selected from N and C (R 23 ), X 24 Selected from N and C (R 24 ), X 25 Selected from N and C (R 25 ), selected from X 21 To X 25 At least one of them is N,
[0043] R 21 To R 26 Each independently selected from a group represented by any one of Formulas 9-1 to 9-3, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, 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 -C10 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 fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ), and is selected from R 21 To R 26 At least one of the groups represented by Formula 9-1 and the groups represented by Formula 9-2,
[0044] Where Q 1 To Q 3 are each 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,
[0045] Formula 9-1 Formula 9-2 Formula 9-3
[0046] *-(L 91 ) a91 -R 91 *-(L 92 ) a92 -R 92 *-(L 93 ) a93 -R 93 ,
[0047] b26 is selected from 1, 2, 3, 4, 5 and 6,
[0048] In formulas 9-1 to 9-3,
[0049] L 91 Selected from each selected from C 1 -C 60 Alkyl and C 3 -C 10 At least one substituted C 6 -C 60 Arylene and C 1 -C 60 Heteroarylene,
[0050] L 92 and L 93 are each independently selected from substituted or unsubstituted C 6 -C 60 Arylene and substituted or unsubstituted C 1 -C 60 Heteroarylene,
[0051] a91 is selected from 1 and 2,
[0052] a92 and a93 are each independently selected from 0, 1 and 2,
[0053] R 91 and R 93 are each independently selected from substituted or unsubstituted C 6 -C 60 Aryl and substituted or unsubstituted C 1 -C 60 Heteroaryl,
[0054] R 92 Selected from each selected from C 1 -C 60 Alkyl and C 3 -C 10 At least one substituted C6 -C 60 Aryl and C 1 -C 60 heteroaryl, and
[0055] * and *' each independently indicate a binding site to an adjacent atom. BRIEF DESCRIPTION OF THE DRAWINGS
[0056] These and / or other aspects will become apparent and more readily understood from the following description of the embodiments, taken in conjunction with the accompanying drawings, in which:
[0057] Figure 1 is a schematic cross-sectional view of an organic light-emitting device according to an embodiment;
[0058] Figure 2 is a schematic cross-sectional view of an organic light-emitting device according to another embodiment;
[0059] Figure 3 is a schematic cross-sectional view of an organic light-emitting device according to another embodiment; and
[0060] Figure 4 is a schematic cross-sectional view of an organic light-emitting device according to another embodiment. DETAILED DESCRIPTION
[0061] The present disclosure will now be described in more detail with reference to example embodiments. However, the present invention can be embodied in many different forms and should not be construed as being limited to the embodiments listed herein; on the contrary, these embodiments are provided so that the present disclosure will be sufficient and complete, and the concepts of the present disclosure will be fully conveyed to those skilled in the art. The advantages and features of the present disclosure and methods of achieving them will become apparent by reference to the described embodiments and the accompanying drawings. However, the present invention can be embodied in many different forms and should not be construed as being limited to the example embodiments.
[0062] Hereinafter, the embodiments are described in more detail by referring to the accompanying drawings, and in the drawings, the same reference numerals denote the same elements and excessive explanation will not be provided herein.
[0063] As used herein, the singular forms “a”, “an” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise.
[0064] It will be further understood that the terms “comprises” and / or “comprising” as used herein refer to the presence of recited features or components, but do not preclude the presence or addition of one or more other features or components.
[0065] It should be understood that when a layer, region, or component is referred to as being "on" or "over" another layer, region, or component, it may be formed directly or indirectly on the other layer, region, or component. That is, for example, one or more intervening layers, regions, or components may be present. In contrast, when an element is referred to as being "directly on" or "directly contacting" another element, there are no intervening elements.
[0066] For convenience of explanation, the sizes of components in the drawings may be exaggerated. In other words, since the sizes and thicknesses of components in the drawings may be arbitrarily illustrated for convenience of explanation, the following embodiments of the present disclosure are not limited thereto.
[0067] The expression “(the organic layer) includes the first compound” may refer to the case where the (organic layer) includes the first compound represented by Formula 1 and the case where the (organic layer) includes two or more different first compounds represented by Formula 1.
[0068] The term "organic layer" used herein refers to a single layer and / or multiple layers between a first electrode and a second electrode in an organic light-emitting device. Materials included in the "organic layer" include but are not limited to organic materials.
[0069] Expressions such as “at least one of,” “one of,” and “selected from,” when preceding a list of elements, modify the entire list of elements rather than the individual elements in the list. In addition, the use of “may” when describing embodiments of the present invention means “one or more embodiments of the present invention.”
[0070] According to one or more embodiments, the organic light-emitting device may include a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, the organic layer including a light-emitting layer,
[0071] The organic layer may include a first compound represented by Formula 1 and a second compound represented by Formula 2, and the first compound may not include 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP):
[0072] Formula 1
[0073]
[0074] Formula 1-1
[0075]
[0076] Formula 2
[0077]
[0078] Formula 9-1 Formula 9-2 Formula 9-3
[0079] *-(L91 ) a91 -R 91 *-(L 92 ) a92 -R 92 *-(L 93 ) a93 -R 93
[0080] Ar in Formula 1 11 It may be a group represented by Formula 1-1; A in Formula 1-1 11 , A 12 , X 11 , X 12 , R 101 , R 102 , b101 and b102 are the same as described below, and * and *' each independently indicates a binding site with an adjacent atom.
[0081] In Formula 1, m11 indicates Ar 11 , and m11 can be selected from 1 and 2.
[0082] A in formula 1-1, 8-1 and 8-2 11 , A 12 , A 81 and A 82 Can be independently selected from C 5 -C 20 Carbocyclic groups and C 1 -C 20 Heterocyclic group.
[0083] For example, A in formulas 1-1, 8-1, and 8-2 11 , A 12 , A 81 and A 82The phenyl group may be independently selected from phenyl, naphthyl, phenanthrenyl, anthracenyl, triphenylene radical, pyrenyl, chrysene, furanyl, thienyl, pyrrolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, 2,6-naphthyridinyl, 1,8-naphthyridinyl, 1,5-naphthyridinyl, 1,6-naphthyridinyl, 1,7-naphthyridinyl, 2,7-naphthyridinyl, quinoxalinyl, quinazolinyl, phenanthridinyl, phenanthrolinyl, benzofuranyl, benzothiophenyl, indene yl, indolyl, furopyridyl, thienopyridyl, cyclopentylpyridyl, pyrrolopyridyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, carbazolyl, benzofuranopyrrolyl, benzothiophenylpyrrolyl, indenopyrrolyl, indolopyrrolyl, benzofuranothiphenyl, benzothiophenylthiophenyl, indenothiophenyl, indolothiphenyl, benzofuranofuranyl, benzothiophenylfuranyl, indenofuranyl, indolofuranyl, benzofuranothiphenyl, benzothiophenylfuranyl, indenofuranyl, indolofuranyl, benzofuranothiphenyl pyridyl, benzothienopyridyl, indenopyridyl, indolopyridyl, benzofuranopyrimidinyl, benzothienopyrimidinyl, indenopyrimidinyl, indolopyrimidinyl, benzofuranoindolyl, benzothienoindolyl, indenoindolyl, indolinoindolyl, benzofuranobenzofuranyl, benzothienobenzofuranyl, indenobenzofuranyl, indolobenzofuranyl, benzofuranobenzothiophene, benzothienobenzothiophene, indenobenzo Thienyl, indolebenzothienyl, benzofuranoquinolyl, benzothiophenequinolyl, indenoquinolyl, indolequinolyl, benzonaphthofuranyl, benzonaphthothienyl, benzofluorenyl, benzocarbazolyl, dinaphthofuranyl, dinaphthothienyl, dibenzofluorenyl, dibenzocarbazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, naphthofuranyl, naphthothienyl, cyclopentanaphthyl, spiro-bifluorenyl and spiro-fluorene-indenyl, but are not limited thereto.
[0084] In various embodiments, A in Formulas 1-1, 8-1, and 8-2 11 and A 81 may be each independently selected from phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl and phenanthrolinyl, and
[0085] A 12 and A 82The phenyl group may be independently selected from phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl, phenanthrolinyl, benzofuranyl, benzothiophenyl, indenyl, indolyl, furopyridyl, thienopyridyl, cyclopentylpyridyl, pyrrolopyridyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, carbazolyl, benzofuranopyridyl, benzothienopyridyl, indenopyridine The invention also includes benzophenone, benzofuranopyrimidinyl, benzothiophenopyrimidinyl, indenopyrimidinyl, indolpyrimidinyl, benzonaphthofuranyl, benzonaphthothiophenyl, benzofluorenyl, benzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, naphthofuranyl and naphthothiophenyl, but is not limited thereto.
[0086] X in formula 1-1 11 Can be selected from N[(L 13 ) a13 -R 13 ]、C[(L 13 ) a13 -R 13 ][(L 14 ) a14 -R 14 ], O and S,
[0087] X 12 can be selected from a single bond, N[(L 15 ) a15 -R 15 ]、C[(L 15 ) a15 -R 15 ][(L 16 ) a16 -R 16 ], O and S,
[0088] Where L 13 To L 16 、a13 to a16、R 13 and R 16 Same as described below.
[0089] For example, X in formula 1-1 11 It can be N[(L 13 ) a13 -R 13 ],and
[0090] X 12 It may be a single bond, but the embodiment is not limited thereto.
[0091] In various embodiments, X in Formula 1-1 11 It can be C[(L 13 ) a13-R 13 ][(L 14 ) a14 -R 14 ],and
[0092] X 12 It may be a single bond, but the embodiment is not limited thereto.
[0093] In various embodiments, X in Formula 1-1 11 can be O, and
[0094] X 12 It may be a single bond, but the embodiment is not limited thereto.
[0095] In various embodiments, X in Formula 1-1 11 can be S, and
[0096] X 12 It may be a single bond, but the embodiment is not limited thereto.
[0097] X in formula 8-1 and 8-2 81 Can be selected from N[(L 81 ) a81 -R 81 ]、C[(L 81 ) a81 -R 81 ][(L 82 ) a82 -R 82 ], O and S, X 82 can be selected from a single bond, N[(L 83 ) a83 -R 83 ]、C[(L 83 ) a83 -R 83 ][(L 84 ) a84 -R 84 ], O and S,
[0098] Where L 81 To L 84 , a81 to a84 and R 81 To R 84 Same as described below.
[0099] For example, X in equations 8-1 and 8-2 81 It can be N[(L 81 ) a81 -R 81 ],and
[0100] X 82 It may be a single bond, but the embodiment is not limited thereto.
[0101] L in Formulas 1, 1-1, 1-2, 8-1 and 8-2 11 To L 16 and L 81 To L 84 can be independently selected from *-O-*', *-S-*', *-C(=O)-*', *-P(=O)(Q 1 )-*'、*-Si(Q 1 )(Q 2 )-*', substituted or unsubstituted C 6 -C 60 Arylene and substituted or unsubstituted C 1 -C 60 Heteroarylene,
[0102] Where Q 1 and Q 2 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, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group.
[0103] For example, L in Formulas 1, 1-1, 1-2, 8-1, and 8-2 11 To L 16 and L 81 To L 84 can be independently selected from the group consisting of:
[0104] *-Si(CH 3 ) 2 *'、*-Si(CH 3 )(Ph)-*'、*-Si(Ph) 2-*', phenylene, naphthylene, phenanthrylene, anthracenylene, triphenylene, pyrenylene, chrysene, pyridylene, pyrazylene, pyrimidylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridylene, quinoxalylene, quinazolinylene, phenanthridylene, acridinylene, phenanthrolinylene and triazinylene;
[0105] phenylene, naphthylene, phenanthrenylene, anthracenylene, triphenylene, pyrenylene, chrysene, pyridinylene, pyrazinylene, pyrimidinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalylene, quinazolinylene, phenanthridinylene, acridinylene, phenanthrolinylene and triazinylene, each of which is substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, tetracenyl, phenanthrenyl, peryl, pentaphenyl, hexacenyl, pentacecenyl, rubenyl, coronenyl, ovalenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isothiazolyl, oxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 );as well as
[0106] phenylene, naphthylene, phenanthrenylene, anthracenylene, triphenylene, pyrenylene, chrysene, pyridylene, pyrazylene, pyrimidylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridylene, quinoxalylene, quinazolinylene, phenanthridylene, acridinylene, phenanthrolinylene and triazinylene, each of which is substituted by at least one member selected from the group consisting of:
[0107] Each is selected from deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl, C 1 -C 20 At least one substituted cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, tetracenyl, phenanthrenyl, peryl, pentaphenyl, hexacenyl, pentacene, rubenyl, coronenyl, ovalenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiophene oxazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl and dibenzocarbazolyl,
[0108] Where Q 31 To Q 33 The groups may be each independently selected from hydrogen, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a tert-butyl group, a phenyl group, a biphenyl group, and a terphenyl group, but the embodiment is not limited thereto.
[0109] In various embodiments, L in Formulas 1, 1-1, 1-2, 8-1, and 8-2 11 To L 16 and L 81 To L 84 can be independently selected from the group consisting of:
[0110] *-Si(CH 3 ) 2 *'、*-Si(Ph) 2 -*', phenylene, naphthylene, pyridylene, pyrazinylene, pyrimidinylene, quinolylene, isoquinolylene, naphthyridinylene, quinoxalinylene and triazinylene;
[0111] phenylene, naphthylene, pyridylene, pyrazinylene, pyrimidylene, quinolylene, isoquinolylene, naphthyridylene, quinoxalylene and triazinylene, each substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triazinyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 );as well as
[0112] phenylene, naphthylene, pyridylene, pyrazinylene, pyrimidylene, quinolylene, isoquinolylene, naphthyridylene, quinoxalylene and triazinylene, each substituted by at least one member selected from the group consisting of:
[0113] Each is selected from deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl, C 1 -C 20 at least one substituted phenyl group of the alkoxy group and the phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthryl group, anthracenyl group, pyrenyl group, chrysene group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolyl group, isoquinolyl group, quinoxalinyl group, quinazolinyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group and triazinyl group,
[0114] Where Q 31 To Q 33 The groups may be each independently selected from hydrogen, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a tert-butyl group, a phenyl group, a biphenyl group, and a terphenyl group, but the embodiment is not limited thereto.
[0115] In various embodiments, L in Formulas 1, 1-1, 1-2, 8-1, and 8-2 11 To L 16 and L81 To L 84 can be independently selected from *-Si(CH 3 ) 2 *'、*-Si(Ph) 2 -*' and a group represented by any one of Formulae 3-1 to 3-13 and 3-16 to 3-163, but not limited thereto:
[0116]
[0117]
[0118]
[0119]
[0120]
[0121]
[0122] Wherein, in Formulas 3-1 to 3-13 and 3-16 to 3-163,
[0123] R 31 You can choose from the group consisting of:
[0124] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triazinyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 );as well as
[0125] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl and triazinyl, each of which is substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl and terphenyl,
[0126] Where Q 31 To Q 33 may be each independently selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, biphenyl and terphenyl,
[0127] b31 can be selected from 1, 2, 3 and 4,
[0128] b32 can be selected from 1, 2, 3, 4, 5 and 6,
[0129] b33 can be selected from 1, 2 and 3,
[0130] b34 can be selected from 1 and 2,
[0131] b35 can be 1, 2, 3, 4, and 5, and
[0132] * and *' can each independently indicate a binding site with an adjacent atom.
[0133] a11 to a16 and a81 to a84 in Formulae 1, 1-1, 1-2, 8-1 and 8-2 may each be independently selected from 0, 1, 2 and 3. When a11 is zero, (L 11 ) a11 It may be a single bond, and when a11 is 2 or greater, multiple L 11 The descriptions of a12 to a16 and a81 to a84 are the same as those provided in conjunction with a11.
[0134] For example, a11 to a16 and a81 to a84 in Formulae 1, 1-1, 1-2, 8-1, and 8-2 may each be independently selected from 0, 1, and 2, but are not limited thereto.
[0135] R in formula 1 and 1-1 11 To R 16 Each independently selected from the group represented by Formula 8-1, the group represented by Formula 8-2, hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, nitro, substituted or unsubstituted C 1 -C 60Alkyl, 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, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ), where R 13 and R 14 may be optionally linked to each other to form a ring and R 15 and R 16 may be optionally linked to each other to form a ring,
[0136] Where Q 1 To Q 3 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 -C10 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.
[0137] For example, R in formula 1 and 1-1 11 To R 16 can be independently selected from the group consisting of:
[0138] A group represented by Formula 8-1, a group represented by Formula 8-2, C 1 -C 20 Alkyl, C 6 -C 30 Aryl and C 1 -C 30 heteroaryl;
[0139] Each of the following C 6 -C 30 Aryl and C 1 -C 30 Heteroaryl: deuterium, -F, -Cl, -Br, -I, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, C 3 -C 10 Cycloalkyl, C 6 -C 30 Aryl, C 1 -C 30 Heteroaryl, -N(Q 31 )(Q 32 ) and -Si(Q 31 )(Q 32 )(Q 33 );as well as
[0140] Each of the following C 6 -C 30 Aryl and C 1 -C 30 Heteroaryl:
[0141] Each is selected from deuterium, -F, -Cl, -Br, -I, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, C 3 -C 10 Cycloalkyl, C 6 -C 30 Aryl, C1 -C 30 Heteroaryl, -N(Q 21 )(Q 22 ) and -Si(Q 21 )(Q 22 )(Q 23 ) at least one substituted C 6 -C 30 Aryl and C 1 -C 30 Heteroaryl,
[0142] Where Q 21 To Q 23 and Q 31 To Q 33 Can be independently selected from C 1 -C 20 Alkyl and C 6 -C 30 An aryl group, but the embodiment is not limited thereto.
[0143] In various embodiments, R in Formula 1 and 1-1 11 To R 16 Can be each independently selected from the group consisting of:
[0144] a group represented by formula 8-1, a group represented by formula 8-2, a methyl group, an ethyl group, an n-propyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a triphenyl group, a phenanthrenyl group, a phenanthrenyl group, a pyrenyl group, a tetraphenyl group, a chrysene group, a fluoranthenyl group, a pyrrolyl group, a furanyl group, a thienyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a triazine group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a pyridopyrimidinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzonaphthyridinyl group, a benzoquinoxalinyl group, a benzoquinazolinyl group, a benzophenanthrolinyl group, a thiazolyl group, an oxazolyl group, an imidazolyl group, a triazolyl group, an indolyl group, a benzimidazolyl group, an imidazopyridinyl group, a benzofuranyl group, a benzothienyl group, and a benzoxazolyl group;
[0145] phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, triphenylene, phenanthrenyl, pyrenyl, tetraphenyl, chrysene, fluoranthenyl, pyrrolyl, furanyl, thienyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, pyridopyrimidinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzonaphthyridinyl, benzoquinoxalinyl, benzoquinazolinyl, benzophenanthrolinyl, thiazolyl, oxazolyl, imidazolyl, triazolyl, indolyl, benzimidazolyl, imidazopyridinyl, benzofuranyl, benzothienyl and benzoxazolyl, each substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, C 1 -C 20Alkyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, -N(Q 31 )(Q 32 ) and -Si(Q 31 )(Q 32 )(Q 33 );as well as
[0146] phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, triphenylene, phenanthrenyl, pyrenyl, tetraphenyl, chrysene, fluoranthenyl, pyrrolyl, furanyl, thienyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, pyridopyrimidinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzonaphthyridinyl, benzoquinoxalinyl, benzoquinazolinyl, benzophenanthrolinyl, thiazolyl, oxazolyl, imidazolyl, triazolyl, indolyl, benzimidazolyl, imidazopyridinyl, benzofuranyl, benzothienyl and benzoxazolyl, each substituted by at least one selected from the following:
[0147] Each is selected from deuterium, -F, -Cl, -Br, -I, C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, -N(Q 21 )(Q 22 ) and -Si(Q 21 )(Q 22 )(Q 23 ) is at least one substituted phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, triphenylene, phenanthrenyl, pyrenyl, tetraphenyl, chrysene, pyrrolyl, furanyl, thienyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzphenanthrolinyl, thiazolyl, oxazolyl, imidazolyl, triazolyl, indolyl, benzimidazolyl, benzofuranyl, benzothiophenyl and benzoxazolyl,
[0148] Where Q 21 To Q 23 and Q 31 To Q 33 The groups may be each independently selected from a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but the embodiment is not limited thereto.
[0149] In various embodiments, R in Formula 1 and 1-1 11 To R 16Each may be independently selected from a group represented by Formula 8-1, a group represented by Formula 8-2, a methyl group, an ethyl group, an n-propyl group, and a group represented by any one of Formulae 5-1 to 5-55 and 5-80 to 5-92, but is not limited thereto:
[0150]
[0151]
[0152]
[0153] Wherein, in Formulas 5-1 to 5-55 and 5-80 to 5-92,
[0154] R 51 To R 53 Can be each independently selected from the group consisting of:
[0155] Hydrogen, deuterium, -F, -Cl, -Br, -I, C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, -N(Q 31 )(Q 32 ) and -Si(Q 31 )(Q 32 )(Q 33 );as well as
[0156] phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, triphenylene, phenanthrenyl, pyrenyl, tetraphenyl, chrysene, pyrrolyl, furanyl, thienyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzphenanthrolinyl, thiazolyl, oxazolyl, imidazolyl, triazolyl, indolyl, benzimidazolyl, benzofuranyl, benzothiophenyl and benzoxazolyl, each substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, -N(Q 21 )(Q 22 ) and -Si(Q 21 )(Q 22 )(Q 23 ),
[0157] Where Q 21 To Q 23 and Q 31 To Q 33may be each independently selected from phenyl, biphenyl, terphenyl and naphthyl,
[0158] b51 can be selected from 1, 2, 3, 4 and 5,
[0159] b52 can be selected from 1, 2, 3, 4, 5, 6 and 7,
[0160] b53 may be selected from 1, 2, 3, 4, 5 and 6,
[0161] b54 can be selected from 1, 2 and 3,
[0162] b55 can be selected from 1, 2, 3 and 4,
[0163] b56 can be 1 or 2, and
[0164] *Indicates the binding site with the neighboring atoms.
[0165] n11 in Formula 1 indicates that 11 ) a11 -R 11 The number of parts represented by n11 can be selected from 0, 1, 2, 3 and 4. When n11 is zero, A in Formula 1-1 11 (wherein the compound represented by Formula 1-1 represents Ar in Formula 1 11 ) has not been by *-(L 11 ) a11 -R 11 When n11 is 2 or more, multiple substitutions represented by *-(L 11 ) a11 -R 11 The represented parts may be the same as or different from each other.
[0166] n12 in Formula 1 indicates that 12 ) a12 -R 12 The number of parts represented by n12 can be selected from 0, 1, 2, 3 and 4. When n12 is zero, A in Formula 1-1 12 (wherein the compound represented by Formula 1-1 represents Ar in Formula 1 11 ) has not been by *-(L 12 ) a12 -R 12 When n12 is 2 or more, multiple substitutions represented by *-(L 12 ) a12 -R 12 The represented parts may be the same as or different from each other.
[0167] For example, the sum of n11 and n12 in Formula 1 may be selected from 0 and 1, but is not limited thereto.
[0168] R in formula 8-1 and 8-2 81 To R 84 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, nitro, substituted or unsubstituted C 1 -C 60 Alkyl, 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, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ),
[0169] Where Q 1 To Q 3 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 10Cycloalkenyl, 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.
[0170] For example, R in formulas 8-1 and 8-2 81 To R 84 Can be each independently selected from the group consisting of:
[0171] C 1 -C 20 Alkyl, C 6 -C 30 Aryl and C 1 -C 30 heteroaryl;
[0172] Each of the following C 6 -C 30 Aryl and C 1 -C 30 Heteroaryl: deuterium, -F, -Cl, -Br, -I, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, C 3 -C 10 Cycloalkyl, C 6 -C 30 Aryl, C 1 -C 30 Heteroaryl, -N(Q 31 )(Q 32 ) and -Si(Q 31 )(Q 32 )(Q 33 );as well as
[0173] Each of the following C 6 -C 30 Aryl and C 1 -C 30 Heteroaryl: each selected from deuterium, -F, -Cl, -Br, -I, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, C 3 -C 10 Cycloalkyl, C 6 -C 30 Aryl, C 1 -C30 Heteroaryl, -N(Q 21 )(Q 22 ) and -Si(Q 21 )(Q 22 )(Q 23 ) at least one substituted C 6 -C 30 Aryl and C 1 -C 30 Heteroaryl,
[0174] Where Q 21 To Q 23 and Q 31 To Q 33 Can be independently selected from C 1 -C 20 Alkyl and C 6 -C 30 An aryl group, but the embodiment is not limited thereto.
[0175] In various embodiments, R in Formulas 8-1 and 8-2 81 To R 84 Can be each independently selected from the group consisting of:
[0176] methyl, ethyl, n-propyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, triphenylene, phenanthrenyl, pyrenyl, tetraphenylene, chrysene, fluoranthenyl, pyrrolyl, furanyl, thienyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, pyridopyrimidinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzonaphthyridinyl, benzoquinoxalinyl, benzoquinazolinyl, benzophenanthrolinyl, thiazolyl, oxazolyl, imidazolyl, triazolyl, indolyl, benzimidazolyl, imidazopyridinyl, benzofuranyl, benzothienyl and benzoxazolyl;
[0177] phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, triphenylene, phenanthrenyl, pyrenyl, tetraphenyl, chrysene, fluoranthenyl, pyrrolyl, furanyl, thienyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, pyridopyrimidinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzonaphthyridinyl, benzoquinoxalinyl, benzoquinazolinyl, benzophenanthrolinyl, thiazolyl, oxazolyl, imidazolyl, triazolyl, indolyl, benzimidazolyl, imidazopyridinyl, benzofuranyl, benzothienyl and benzoxazolyl, each substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, C 1 -C 20Alkyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, -N(Q 31 )(Q 32 ) and -Si(Q 31 )(Q 32 )(Q 33 );as well as
[0178] phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, triphenylene, phenanthrenyl, pyrenyl, tetraphenyl, chrysene, fluoranthenyl, pyrrolyl, furanyl, thienyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, pyridopyrimidinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzonaphthyridinyl, benzoquinoxalinyl, benzoquinazolinyl, benzo-o-phenanthrolinyl, thiazolyl, oxazolyl, imidazolyl, triazolyl, indolyl, benzimidazolyl, imidazopyridinyl, benzofuranyl, benzothienyl and benzoxazolyl, each substituted by at least one selected from the group consisting of:
[0179] Each is selected from deuterium, -F, -Cl, -Br, -I, C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, -N(Q 21 )(Q 22 ) and -Si(Q 21 )(Q 22 )(Q 23 ) is at least one substituted phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, triphenylene, phenanthrenyl, pyrenyl, tetraphenyl, chrysene, pyrrolyl, thienyl, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzphenanthrolinyl, thiazolyl, oxazolyl, imidazolyl, triazolyl, indolyl, benzimidazolyl, benzofuranyl, benzothiophenyl and benzoxazolyl,
[0180] Where Q 21 To Q 23 and Q 31 To Q 33 The groups may be each independently selected from a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but the embodiment is not limited thereto.
[0181] In various embodiments, R in Formulas 8-1 and 8-2 81 To R 84Each may be independently selected from a methyl group, an ethyl group, an n-propyl group and a group represented by any one of Formulae 5-1 to 5-55 and 5-80 to 5-92, but is not limited thereto:
[0182]
[0183]
[0184]
[0185] Wherein, in Formulas 5-1 to 5-55 and 5-80 to 5-92,
[0186] R 51 To R 53 Can be each independently selected from the group consisting of:
[0187] Hydrogen, deuterium, -F, -Cl, -Br, -I, C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, -N(Q 31 )(Q 32 ) and -Si(Q 31 )(Q 32 )(Q 33 );as well as
[0188] phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, triphenylene, phenanthrenyl, pyrenyl, tetraphenyl, chrysene, pyrrolyl, furanyl, thienyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzphenanthrolinyl, thiazolyl, oxazolyl, imidazolyl, triazolyl, indolyl, benzimidazolyl, benzofuranyl, benzothiophenyl and benzoxazolyl, each substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, -N(Q 21 )(Q 22 ) and -Si(Q 21 )(Q 22 )(Q 23 ),
[0189] Where Q 21 To Q 23 and Q 31 To Q 33 may be each independently selected from phenyl, biphenyl, terphenyl and naphthyl,
[0190] b51 can be selected from 1, 2, 3, 4 and 5,
[0191] b52 can be selected from 1, 2, 3, 4, 5, 6 and 7,
[0192] b53 may be selected from 1, 2, 3, 4, 5 and 6,
[0193] b54 can be selected from 1, 2 and 3,
[0194] b55 can be selected from 1, 2, 3 and 4,
[0195] b56 can be 1 or 2, and
[0196] *Indicates the binding site with the neighboring atoms.
[0197] R in Formula 1, 1-1, 8-1 and 8-2 101 , R 102 , R 85 and R 86 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, nitro, substituted or unsubstituted C 1 -C 60 Alkyl, 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, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1)(Q 2 ),
[0198] Where Q 1 To Q 3 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, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group.
[0199] For example, R in Formulas 1, 1-1, 8-1, and 8-2 101 , R 102 , R 85 and R 86 Can be each independently selected from the group consisting of:
[0200] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 30 Aryl, C 6 -C 30 Aryloxy, C 6 -C 30 Arylthio, C 1 -C 30 Heteroaryl and -Si(Q 1 )(Q2 )(Q 3 );
[0201] Each is selected from deuterium, -F, -Cl, -Br, -I, cyano and -Si(Q 31 )(Q 32 )(Q 33 ) at least one substituted C 1 -C 20 Alkyl and C 3 -C 10 Cycloalkyl; and
[0202] Each of the following C 6 -C 30 Aryl and C 1 -C 30 Heteroaryl:
[0203] Each is selected from deuterium, -F, -Cl, -Br, -I, cyano and -Si(Q 21 )(Q 22 )(Q 23 ) at least one substituted C 1 -C 20 Alkyl, C 6 -C 30 Aryl and C 1 -C 30 Heteroaryl,
[0204] Where Q 1 To Q 3 , Q 21 To Q 23 and Q 31 To Q 33 Can be independently selected from C 1 -C 20 Alkyl, C 6 -C 30 Aryl, C 1 -C 30 A heteroaryl group, a biphenyl group, and a terphenyl group, but the embodiment is not limited thereto.
[0205] In various embodiments, R in Formulas 1, 1-1, 8-1, and 8-2 101 , R 102 , R 85 and R 86 Can be each independently selected from the group consisting of:
[0206] hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl and -Si(Q) 1 )(Q 2 )(Q 3 );
[0207] methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl, each substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, cyano and -Si(Q) 31 )(Q 32 )(Q 33 );as well as
[0208] Phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidyl, pyridazinyl, triazinyl, quinolyl and isoquinolyl, each substituted by at least one member selected from the group consisting of:
[0209] Each is selected from deuterium, -F, -Cl, -Br, -I, cyano and -Si(Q 21 )(Q 22 )(Q 23 ) is at least one substituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidyl, pyridazinyl, triazinyl, quinolyl and isoquinolyl,
[0210] Where Q 1 To Q 3 , Q 21 To Q 23 and Q 31 To Q 33 The groups may be each independently selected from a methyl group and a phenyl group, but the embodiment is not limited thereto.
[0211] b101, b102, b85 and b86 in Formula 1, 1-1, 8-1 and 8-2 may be independently selected from 1, 2, 3, 4, 5 and 6. When b101 is 2 or more, a plurality of R 101 The descriptions of b102, b85, and b86 may each independently be the same as the description provided in conjunction with b101.
[0212] The case where the first compound represented by Formula 1 is 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP) may be excluded.
[0213] For example, when m11 in equation 1 is 1, n11 and n12 are both zero, X 11 N[(L 13) a13 -R 13 ] and R 13 When the group is represented by Formula 8-2, (L 13 ) a13 The situation expressed by formula 10-1:
[0214]
[0215] Wherein * and *' in Formula 10-1 each independently indicate a binding site with an adjacent atom.
[0216] For example, the group represented by Formula 1-1 may be selected from the groups represented by Formulas 1-11 to 1-67, but is not limited thereto:
[0217]
[0218]
[0219]
[0220]
[0221]
[0222]
[0223]
[0224]
[0225] Wherein, in Formulas 1-11 to 1-67,
[0226] A 11 and A 13 may be each independently selected from phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl and phenanthroline,
[0227] X 11 Can be selected from N[(L 13 ) a13 -R 13 ]、C[(L 13 ) a13 -R 13 ][(L 14 ) a14 -R 14 ], O and S,
[0228] X 14 Can be selected from C(R 101d )(R 101e )、N(R 101d), O and S,
[0229] L 13 , L 14 、a13、a14、R 13 , R 14 , R 101 , R 102 The descriptions of b101 and b102 are the same as those provided in conjunction with Formula 1,
[0230] R 101a , R 101b , R 101c , R 101d and R 101e The descriptions are independently combined with R of Formula 1 101 The same ones provided,
[0231] The descriptions of b101a and b101b are each independently the same as those provided in conjunction with b101 of Formula 1, and
[0232] * and *' each independently indicate a binding site to an adjacent atom.
[0233] For example, the group represented by Formula 8-1 and the group represented by Formula 8-2 may each be independently selected from the groups represented by Formulae 8-11 to 8-44, but are not limited thereto:
[0234]
[0235]
[0236]
[0237]
[0238] Among them, in formulas 8-11 to 8-44,
[0239] A 81 and A 83 may be each independently selected from phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl and phenanthroline,
[0240] X 81 Can be selected from N[(L 81 ) a81 -R 81 ]、C[(L 81 ) a81 -R 81 ][(L 82 ) a82 -R 82 ], O and S,
[0241] X83 Can be selected from C(R 85c )(R 85d )、N(R 85c ), O and S,
[0242] L 81 , L 82 、a81、a82、R 81 , R 82 , R 85 , R 86 The descriptions of b85 and b86 are the same as those provided in conjunction with equations 8-1 and 8-2,
[0243] R 85a , R 85b , R 85c and R 85d The descriptions are independently combined with R in formula 8-1 and 8-2 85 The same ones provided,
[0244] The descriptions of b85a and b86b are each independently the same as those provided in conjunction with b85 in equation 8-1, and
[0245] * and *' each independently indicate a binding site to an adjacent atom.
[0246] A in Formula 2 21 Can be selected from C 6 -C 20 Aromatic groups and C 1 -C 20 Heteroaromatic groups.
[0247] For example, A in Formula 2 21 The group may be selected from phenyl, naphthyl, phenanthryl, anthracenyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, quinoxalinyl and quinazolinyl, but is not limited thereto.
[0248] In various embodiments, A in Formula 2 21 The group may be selected from phenyl, pyridyl, pyrazinyl, pyrimidinyl and triazine, but is not limited thereto.
[0249] In formula 2, X 21 Can be selected from N and C (R 21 ), X 22 Can be selected from N and C (R 22 ), X 23 Can be selected from N and C (R 23 ), X 24 Can be selected from N and C (R 24 ), and X 25 Can be selected from N and C (R 25 ), where X21 To X 25 At least one of them can be N and R 21 To R 25 Same as described below.
[0250] For example, in Formula 2, X 21 Can be N, X 22 It can be C(R 22 ), X 23 It can be C(R 23 ), X 24 It can be C(R 24 ), and X 25 It can be C(R 25 );
[0251] X 21 It can be C(R 21 ), X 22 Can be N, X 23 It can be C(R 23 ), X 24 It can be C(R 24 ), and X 25 It can be C(R 25 );
[0252] X 21 It can be C(R 21 ), X 22 It can be C(R 22 ), X 23 Can be N, X 24 It can be C(R 24 ), and X 25 It can be C(R 25 );
[0253] X 21 It can be C(R 21 ), X 22 It can be C(R 22 ), X 23 It can be C(R 23 ), X 24 Can be N, and X 25 It can be C(R 25 );
[0254] X 21 It can be C(R 21 ), X 22 It can be C(R 22 ), X 23 It can be C(R 23 ), X 24 It can be C(R 24 ), and X25 Can be N;
[0255] X 21 Can be N, X 22 It can be C(R 22 ), X 23 It can be C(R 23 ), X 24 It can be C(R 24 ), and X 25 Can be N;
[0256] X 21 Can be N, X 22 It can be C(R 22 ), X 23 Can be N, X 24 It can be C(R 24 ), and X 25 It can be C(R 25 );
[0257] X 21 It can be C(R 21 ), X 22 It can be C(R 22 ), X 23 Can be N, X 24 It can be C(R 24 ), and X 25 Can be N; or
[0258] X 21 Can be N, X 22 It can be C(R 22 ), X 23 Can be N, X 24 It can be C(R 24 ), and X 25 It may be N, but the implementation is not limited thereto.
[0259] R in Formula 2 21 To R 26 Each independently selected from a group represented by any one of Formulas 9-1 to 9-3, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, 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 C3 -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 fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ), and is selected from R 21 To R 26 At least one of the groups may be selected from the group represented by Formula 9-1 and the group represented by Formula 9-2,
[0260] Where Q 1 To Q 3 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.
[0261] For example, R in Formula 2 21 To R 26 Can be each independently selected from the group consisting of:
[0262] A group represented by any one of Formulae 9-1 to 9-3, hydrogen, C 1 -C 20 Alkyl and C 3 -C 10 Cycloalkyl;
[0263] C 6 -C 30 Aryl, C 1 -C 30 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups;
[0264] Each of the following C 6 -C 30 Aryl, C 1 -C 30 Heteroaryl, monovalent non-aromatic fused polycyclic group, and monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, C 1 -C 20 Alkyl, C 3 -C 10 Cycloalkyl, C 6 -C 30 Aryl, C 1 -C 30 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 31 )(Q 32 ) and -Si(Q 31 )(Q 32 )(Q 33 );as well as
[0265] Each of the following C 6 -C 30 Aryl, C 1 -C 30 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups:
[0266] Each is selected from deuterium, -F, -Cl, -Br, -I, C 1 -C 20 Alkyl, C 3 -C 10 Cycloalkyl, C 6 -C30 Aryl, C 1 -C 30 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 22 ) and -Si(Q 21 )(Q 22 )(Q 23 ) at least one substituted C 6 -C 30 Aryl, C 1 -C 30 heteroaryl, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heteropolycyclic group,
[0267] Where Q 21 To Q 23 and Q 31 To Q 33 Can be independently selected from C 1 -C 20 Alkyl and C 6 -C 30 An aryl group, but the embodiment is not limited thereto.
[0268] In various embodiments, R in Formula 2 21 To R 26 Can be each independently selected from the group consisting of:
[0269] a group represented by any one of formulae 9-1 to 9-3, hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, and cyclohexyl;
[0270] phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, triphenylene, phenanthrenyl, pyrenyl, tetraphenyl, chrysene, pyrrolyl, furanyl, thienyl, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzophenanthrolinyl, thiazolyl, oxazolyl, imidazolyl, triazolyl, indolyl, benzimidazolyl, benzofuranyl, benzothienyl, benzoxazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, fluorenyl, spiro-cyclopentane-fluorenyl, spiro-bifluorenyl, benzonaphthofuranyl, benzonaphthothienyl, benzocarbazolyl, and benzofluorenyl;
[0271] phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, triphenylene, phenanthrenyl, pyrenyl, tetraphenyl, chrysene, pyrrolyl, furanyl, thienyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenyl phenanthroline, thiazolyl, oxazolyl, imidazolyl, triazolyl, indolyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzoxazolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, spiro-cyclopentane-fluorenyl, spiro-bifluorenyl, benzonaphthofuranyl, benzonaphthothiophenyl, benzocarbazolyl and benzofluorenyl: deuterium, -F, -Cl, -Br, -I, C 1 -C 20 Alkyl, C 3 -C 10 Cycloalkyl, C 6 -C 30 Aryl, C 1 -C 30 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 31 )(Q 32 ) and -Si(Q 31 )(Q 32 )(Q 33 );as well as
[0272] phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, triphenylene, phenanthrenyl, pyrenyl, tetraphenyl, chrysene, pyrrolyl, furanyl, thienyl, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzophenanthrolinyl, thiazolyl, oxazolyl, imidazolyl, triazolyl, indolyl, benzimidazolyl, benzofuranyl, benzothienyl, benzoxazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, fluorenyl, spiro-cyclopentane-fluorenyl, spiro-bifluorenyl, benzonaphthofuranyl, benzonaphthothienyl, benzocarbazolyl and benzofluorenyl, each substituted with at least one member selected from the group consisting of:
[0273] Each is selected from deuterium, -F, -Cl, -Br, -I, C 1 -C 20 Alkyl, C 3 -C 10 Cycloalkyl, C 6 -C 30 Aryl, C 1 -C 30 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q22 ) and -Si(Q 21 )(Q 22 )(Q 23 ) is at least one substituted phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidyl, pyridazinyl and triazinyl,
[0274] Where Q 21 To Q 23 and Q 31 To Q 33 The groups may be each independently selected from a methyl group, an ethyl group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but the embodiment is not limited thereto.
[0275] In various embodiments, R in Formula 2 21 To R 26 Each independently may be selected from a group represented by any one of Formulas 9-1 to 9-3, hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl and a group represented by any one of Formulas 5-1 to 5-79, but is not limited thereto:
[0276]
[0277]
[0278]
[0279] Among them, in formulas 5-1 to 5-79,
[0280] X 51 Can be selected from N(R 55 )、C(R 55 )(R 56 ), O and S,
[0281] R 51 To R 56 Can be each independently selected from the group consisting of:
[0282] Hydrogen, deuterium, -F, -Cl, -Br, -I, C 1 -C 20 Alkyl, C 3 -C 10 Cycloalkyl, C 6 -C 30 Aryl, C 1 -C 30 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 31 )(Q 32 ) and -Si(Q 31 )(Q 32 )(Q33 );as well as
[0283] phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidyl, pyridazinyl and triazinyl, each substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, C 1 -C 20 Alkyl, C 3 -C 10 Cycloalkyl, C 6 -C 30 Aryl, C 1 -C 30 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 22 ) and -Si(Q 21 )(Q 22 )(Q 23 ),
[0284] Where Q 21 To Q 23 and Q 31 To Q 33 may be each independently selected from methyl, ethyl, phenyl, biphenyl, terphenyl and naphthyl,
[0285] b51 can be selected from 1, 2, 3, 4 and 5,
[0286] b52 can be selected from 1, 2, 3, 4, 5, 6 and 7,
[0287] b53 may be selected from 1, 2, 3, 4, 5 and 6,
[0288] b54 can be selected from 1, 2 and 3,
[0289] b55 can be selected from 1, 2, 3 and 4,
[0290] b56 can be 1 or 2, and
[0291] *Indicates the binding site with the neighboring atoms.
[0292] b26 in Formula 2 indicates R 26 The number of R 26 May be the same as or different from each other.
[0293] L in formula 9-1 91 Can be selected from each of the C 1 -C 60 Alkyl and C 3 -C 10 Cycloalkyl substituted C 6 -C60 Arylene and C 1 -C 60 Heteroarylene.
[0294] For example, L in formula 9-1 91 Can be selected from each selected from C 1 -C 20 At least one of the alkyl, cyclopentyl, cyclohexyl and cycloheptyl groups may be substituted with phenylene, naphthylene, phenanthrylene, anthracenylene, benzophenanthrylene, pyrenylene, chrysene, pyridylene, pyrazinylene, pyrimidinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridylene, quinoxalylene, quinazolinylene, phenanthridylene, acridinylene, phenanthrolinylene and triazinylene, but is not limited thereto.
[0295] In various embodiments, L in Formula 9-1 91 It can be selected from phenylene, naphthylene, pyridylene, pyrazinylene, pyrimidylene, quinolylene, isoquinolylene, naphthyridylene, quinoxalylene and triazinylene, each of which is substituted by at least one selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl and cycloheptyl, but is not limited thereto.
[0296] In various embodiments, L in Formula 9-1 91 The group represented by the formulae 3-1 to 3-13 and 3-16 to 3-163 may be selected:
[0297]
[0298]
[0299]
[0300]
[0301]
[0302]
[0303] Wherein, in Formulas 3-1 to 3-13 and 3-16 to 3-163,
[0304] R 31 may be selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl and cycloheptyl,
[0305] b31 can be selected from 1, 2, 3 and 4,
[0306] b32 can be selected from 1, 2, 3, 4, 5 and 6,
[0307] b33 can be selected from 1, 2 and 3,
[0308] b34 can be selected from 1 and 2,
[0309] b35 may be selected from 1, 2, 3, 4 and 5, and
[0310] * and *' each independently indicate a binding site to an adjacent atom.
[0311] L in formula 9-2 and 9-3 92 and L 93 may be independently selected from substituted or unsubstituted C 6 -C 60 Arylene and substituted or unsubstituted C 1 -C 60 Heteroarylene.
[0312] For example, L in equations 9-2 and 9-3 92 and L 93 Can be each independently selected from the group consisting of:
[0313] phenylene, naphthylene, phenanthrylene, anthracenylene, triphenylene, pyrenylene, chrysene, pyridylene, pyrazylene, pyrimidylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridylene, quinoxalylene, quinazolinylene, phenanthridylene, acridinylene, phenanthrolinylene and triazinylene;
[0314] phenylene, naphthylene, phenanthrenylene, anthracenylene, triphenylene, pyrenylene, chrysene, pyridinylene, pyrazinylene, pyrimidinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalylene, quinazolinylene, phenanthridinylene, acridinylene, phenanthrolinylene and triazinylene, each of which is substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, tetracenyl, phenanthrenyl, peryl, pentaphenyl, hexacenyl, pentacecenyl, rubenyl, coronenyl, ovalenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isothiazolyl, oxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 );as well as
[0315] phenylene, naphthylene, phenanthrenylene, anthracenylene, triphenylene, pyrenylene, chrysene, pyridylene, pyrazylene, pyrimidylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridylene, quinoxalylene, quinazolinylene, phenanthridylene, acridinylene, phenanthrolinylene and triazinylene, each of which is substituted by at least one member selected from the group consisting of:
[0316] Each is selected from deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl and C 1 -C 20At least one substituted alkoxy group is a cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, tetracenyl, phenanthrenyl, peryl, pentaphenyl, hexacenyl, pentacecenyl, rubenyl, coronenyl, ovalenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl , oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl and dibenzocarbazolyl,
[0317] Where Q 31 To Q 33 The groups may be each independently selected from hydrogen, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a tert-butyl group, a phenyl group, a biphenyl group, and a terphenyl group, but the embodiment is not limited thereto.
[0318] In various embodiments, L in Formulas 9-2 and 9-3 92 and L 93 Can be each independently selected from the group consisting of:
[0319] phenylene, naphthylene, pyridinylene, pyrazinylene, pyrimidinylene, quinolylene, isoquinolylene, naphthyridinylene, quinoxalinylene and triazinylene;
[0320] phenylene, naphthylene, pyridylene, pyrazinylene, pyrimidylene, quinolylene, isoquinolylene, naphthyridylene, quinoxalylene and triazinylene, each substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triazinyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 );as well as
[0321] phenylene, naphthylene, pyridylene, pyrazinylene, pyrimidylene, quinolylene, isoquinolylene, naphthyridylene, quinoxalylene and triazinylene, each substituted by at least one member selected from the group consisting of:
[0322] Each is selected from deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl and C 1 -C 20 at least one substituted phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl and triazinyl of the alkoxy group,
[0323] Where Q 31 To Q 33 The groups may be each independently selected from hydrogen, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a tert-butyl group, a phenyl group, a biphenyl group, and a terphenyl group, but the embodiment is not limited thereto.
[0324] In various embodiments, L in Formulas 9-2 and 9-3 92 and L 93 can be independently selected from the groups represented by the formulae 3-1 to 3-13 and 3-16 to 3-163,
[0325] Wherein, in Formulas 3-1 to 3-13 and 3-16 to 3-163,
[0326] R 31 You can choose from the group consisting of:
[0327] Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, triazinyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 );as well as
[0328] Phenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, quinolyl, isoquinolyl, naphthyridinyl, quinoxalinyl and triazinyl, each of which is substituted by at least one member selected from the group consisting of:
[0329] Each is selected from deuterium, -F, -Cl, -Br, -I, cyano, C 1 -C 20 Alkyl and C 1 -C 20 at least one substituted phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, chrysene, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl and triazinyl of the alkoxy group,
[0330] Where Q 31 To Q 33 may be each independently selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, biphenyl and terphenyl,
[0331] b31 can be selected from 1, 2, 3 and 4,
[0332] b32 can be selected from 1, 2, 3, 4, 5 and 6,
[0333] b33 can be selected from 1, 2 and 3,
[0334] b34 can be selected from 1 and 2,
[0335] b35 may be selected from 1, 2, 3, 4 and 5, and
[0336] * and *' each independently indicates a binding site with an adjacent atom, but the embodiment is not limited thereto.
[0337] a91 in formula 9-1 indicates L 91 The number of, and a91 can be selected from 1 and 2. When a91 is 2, the two L 91 May be the same as or different from each other.
[0338] a92 and a93 in formula 9-2 and 9-3 can be independently selected from 0, 1 and 2. When a92 is zero, (L 92 ) a92 It can indicate a single bond. When a92 is 2, two L 92 The description of a93 may be the same as the description of a92.
[0339] R in formula 9-1 and 9-3 91 and R 93 may be independently selected from substituted or unsubstituted C 6 -C 60 Aryl and substituted or unsubstituted C 1 -C 60 Heteroaryl.
[0340] For example, R in formulas 9-1 and 9-3 91 and R 93 Can be each independently selected from the group consisting of:
[0341] C 6 -C 30 Aryl and C 1 -C 30 heteroaryl;
[0342] Each of the following C 6 -C 30 Aryl and C 1 -C 30 Heteroaryl: deuterium, -F, -Cl, -Br, -I, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, C 3 -C 10 Cycloalkyl, C 6 -C 30 Aryl, C 1 -C 30 Heteroaryl, -N(Q 31 )(Q 32 ) and -Si(Q 31 )(Q 32 )(Q 33 );as well as
[0343] Each of the following C6 -C 30 Aryl and C 1 -C 30 Heteroaryl: each selected from deuterium, -F, -Cl, -Br, -I, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, C 3 -C 10 Cycloalkyl, C 6 -C 30 Aryl, C 1 -C 30 Heteroaryl, -N(Q 21 )(Q 22 ) and -Si(Q 21 )(Q 22 )(Q 23 ) at least one substituted C 6 -C 30 Aryl and C 1 -C 30 Heteroaryl,
[0344] Where Q 21 To Q 23 and Q 31 To Q 33 Can be independently selected from C 1 -C 20 Alkyl and C 6 -C 30 An aryl group, but the embodiment is not limited thereto.
[0345] In various embodiments, R in Formulas 9-1 and 9-3 91 and R 93 Can be each independently selected from the group consisting of:
[0346] phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, triphenylene, phenanthrenyl, pyrenyl, tetraphenylene, chrysene, pyrrolyl, furanyl, thienyl, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzophenanthrolinyl, thiazolyl, oxazolyl, imidazolyl, triazolyl, indolyl, benzimidazolyl, benzofuranyl, benzothiophenyl and benzoxazolyl;
[0347] phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, triphenylene, phenanthrenyl, pyrenyl, tetraphenyl, chrysene, pyrrolyl, furanyl, thienyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzphenanthrolinyl, thiazolyl, oxazolyl, imidazolyl, triazolyl, indolyl, benzimidazolyl, benzofuranyl, benzothiophenyl and benzoxazolyl, each substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, -N(Q 31 )(Q 32 ) and -Si(Q 31 )(Q 32 )(Q 33 );as well as
[0348] phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, triphenylene, phenanthrenyl, pyrenyl, tetraphenyl, chrysene, pyrrolyl, furanyl, thienyl, pyridyl, pyrazinyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzphenanthrolinyl, thiazolyl, oxazolyl, imidazolyl, triazolyl, indolyl, benzimidazolyl, benzofuranyl, benzothienyl and benzoxazolyl, each substituted by at least one member selected from the group consisting of:
[0349] Each is selected from deuterium, -F, -Cl, -Br, -I, C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, -N(Q 21 )(Q 22 ) and -Si(Q 21 )(Q 22 )(Q 23 ) is at least one substituted phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, triphenylene, phenanthrenyl, pyrenyl, tetraphenyl, chrysene, pyrrolyl, furanyl, thienyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzphenanthrolinyl, thiazolyl, oxazolyl, imidazolyl, triazolyl, indolyl, benzimidazolyl, benzofuranyl, benzothiophenyl and benzoxazolyl,
[0350] Where Q 21 To Q 23 and Q 31 To Q33 The phenyl groups may be independently selected from a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group, but are not limited thereto.
[0351] In various embodiments, R in Formulas 9-1 and 9-3 91 and R 93 can be independently selected from the groups represented by the formulae 5-1 to 5-55,
[0352] Among them, in formulas 5-1 to 5-55,
[0353] R 51 To R 53 Can be each independently selected from the group consisting of:
[0354] Hydrogen, deuterium, -F, -Cl, -Br, -I, C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, -N(Q 31 )(Q 32 ) and -Si(Q 31 )(Q 32 )(Q 33 );as well as
[0355] phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, triphenylene, phenanthrenyl, pyrenyl, tetraphenyl, chrysene, pyrrolyl, furanyl, thienyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzphenanthrolinyl, thiazolyl, oxazolyl, imidazolyl, triazolyl, indolyl, benzimidazolyl, benzofuranyl, benzothiophenyl and benzoxazolyl, each substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, C 1 -C 20 Alkyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, -N(Q 21 )(Q 22 ) and -Si(Q 21 )(Q 22 )(Q 23 ),
[0356] Where Q 21 To Q 23 and Q 31 To Q 33 may be each independently selected from phenyl, biphenyl, terphenyl and naphthyl,
[0357] b51 can be selected from 1, 2, 3, 4 and 5,
[0358] b52 can be selected from 1, 2, 3, 4, 5, 6 and 7,
[0359] b53 may be selected from 1, 2, 3, 4, 5 and 6,
[0360] b54 can be selected from 1, 2 and 3,
[0361] b55 can be selected from 1, 2, 3 and 4,
[0362] b56 can be 1 or 2, and
[0363] * indicates a binding site with an adjacent atom, but the embodiment is not limited thereto.
[0364] R in Formula 9-2 92 Can be selected from each selected from C 1 -C 60 Alkyl and C 3 -C 10 At least one substituted C 6 -C 60 Aryl and C 1 -C 60 Heteroaryl.
[0365] For example, R in Formula 9-2 92 You can choose from the group consisting of:
[0366] phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, triphenylene, phenanthrenyl, pyrenyl, tetraphenyl, chrysene, pyrrolyl, furanyl, thienyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzphenanthrolinyl, thiazolyl, oxazolyl, imidazolyl, triazolyl, indolyl, benzimidazolyl, benzofuranyl, benzothiophenyl and benzoxazolyl, each substituted by at least one member selected from the group consisting of: C 1 -C 20 Alkyl, cyclopentyl, cyclohexyl and cycloheptyl, but are not limited thereto.
[0367] In various embodiments, R in Formula 9-2 92The phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, triphenylene, phenanthrenyl, pyrenyl, tetraphenyl, chrysene, pyrrolyl, furanyl, thienyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzophenanthrolinyl, thiazolyl, oxazolyl, imidazolyl, triazolyl, indolyl, benzimidazolyl, benzofuranyl, benzothiophenyl and benzoxazolyl groups may be selected, but are not limited thereto.
[0368] In various embodiments, R in Formula 9-2 92 It can be selected from the groups represented by the formulae 5-1 to 5-55,
[0369] Among them, in formulas 5-1 to 5-55,
[0370] R 51 To R 53 may be each independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopentyl, cyclohexyl and cycloheptyl,
[0371] b51 can be selected from 1, 2, 3, 4 and 5,
[0372] b52 can be selected from 1, 2, 3, 4, 5, 6 and 7,
[0373] b53 may be selected from 1, 2, 3, 4, 5 and 6,
[0374] b54 can be selected from 1, 2 and 3,
[0375] b55 can be selected from 1, 2, 3 and 4,
[0376] b56 can be 1 or 2, and
[0377] * indicates a binding site with an adjacent atom, but the embodiment is not limited thereto.
[0378] For example, the second compound represented by Formula 2 may be represented by Formula 2-1, but is not limited thereto:
[0379] Formula 2-1
[0380]
[0381] In formula 2-1,
[0382] X 21 Can be selected from N and C (R 21 ), X 22 Can be selected from N and C (R22 ), X 23 Can be selected from N and C (R 23 ), X 24 Can be selected from N and C (R 24 ), and X 25 Can be selected from N and C (R 25 ), where X 21 To X 25 At least one of may be N,
[0383] R 21 To R 25 and R 26a To R 26e Each independently selected from a group represented by any one of Formulas 9-1 to 9-3, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, 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 fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ), and is selected from R21 To R 25 and R 26a To R 26e At least one of the groups may be selected from the group represented by Formula 9-1 and the group represented by Formula 9-2,
[0384] Where Q 1 To Q 3 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, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group.
[0385] In various embodiments, the second compound represented by Formula 2 may be represented by one selected from Formulae 2-11 to 2-22, but is not limited thereto:
[0386]
[0387]
[0388] Among them, in formulas 2-11 to 2-22,
[0389] X 21 Can be selected from N and C (R 21 ), X 22 Can be selected from N and C (R 22 ), X 23 Can be selected from N and C (R 23 ), X 24 Can be selected from N and C (R 24 ), and X 25 Can be selected from N and C (R 25 ), where X 21 To X 25At least one of may be N,
[0390] R 21 To R 25 and R 26a To R 26e can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, 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 fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ),
[0391] L 91 , L 91a , L 91b and L 91c Can be independently selected from C 1 -C 60 Alkyl and C 3 -C 10 At least one substituted C 6 -C60 Arylene and C 1 -C 60 Heteroarylene,
[0392] L 92 , L 92a , L 92b and L 92c may be independently selected from substituted or unsubstituted C 6 -C 60 Arylene and substituted or unsubstituted C 1 -C 60 Heteroarylene,
[0393] a91, a91a, a91b and a91c can each be independently selected from 1 and 2,
[0394] a92, a92a, a92b and a92c can each be independently selected from 0, 1 and 2,
[0395] R 91 , R 91a , R 91b and R 91c may be independently selected from substituted or unsubstituted C 6 -C 60 Aryl and substituted or unsubstituted C 1 -C 60 heteroaryl, and
[0396] R 92 , R 92a , R 92b and R 92c Can be independently selected from C 1 -C 60 Alkyl and C 3 -C 10 At least one substituted C 6 -C 60 Aryl and C 1 -C 60 Heteroaryl,
[0397] Where Q 1 To Q 3 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 -C10 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.
[0398] The first compound represented by Formula 1 may be represented by any one of Compounds 1-1 to 1-380, but is not limited thereto:
[0399]
[0400]
[0401]
[0402]
[0403]
[0404]
[0405]
[0406]
[0407]
[0408]
[0409]
[0410]
[0411]
[0412]
[0413]
[0414]
[0415]
[0416]
[0417]
[0418] The second compound represented by Formula 2 may be selected from compounds 2-1 to 2-192, but is not limited thereto:
[0419]
[0420]
[0421]
[0422]
[0423]
[0424]
[0425]
[0426]
[0427]
[0428]
[0429] The first compound represented by Formula 1 may include i) a partial structure in which a 5-membered ring and a 6-membered ring are condensed (e.g., fused), for example, the first compound may include at least one indole group or carbazole group, and ii) various substituents having hole transport capability and substituents having electron transport capability. Therefore, in an organic light-emitting device in which the first compound represented by Formula 1 is included in a light-emitting layer (e.g., included in a light-emitting layer as a host) and / or a buffer layer, the balance of charges in the light-emitting layer (balance of holes and electrons) may be excellent (or suitable) and charges may be smoothly injected into the light-emitting layer, thereby improving the efficiency of the organic light-emitting device.
[0430] When the second compound represented by Formula 2 includes an alkyl group and / or a cycloalkyl group, the second compound may have a low crystallinity. Therefore, when an organic layer is formed using the second compound represented by Formula 2, the quality of the organic layer (e.g., the film-forming characteristics of the organic layer) can be improved. Similarly, since the alkyl group and / or the cycloalkyl group can be used as an intermolecular or intramolecular electron donor, the second compound represented by Formula 2 including an alkyl group and / or a cycloalkyl group may have improved electrochemical stability. Therefore, an organic light-emitting device including a second compound represented by Formula 2 may have high efficiency and a long life.
[0431] Thus, the organic light-emitting device including the first compound and the second compound can have high efficiency and long lifetime, which is at least partially due to the balance of charges in the light-emitting layer and the improved stability of the compounds.
[0432] Figure 1 Description
[0433] Figure 1 1 is a schematic diagram 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 .
[0434] In the following, we will combine Figure 1 A structure of an organic light-emitting device 10 and a method of manufacturing the organic light-emitting device 10 according to an embodiment are described.
[0435] First electrode 110
[0436] exist Figure 1 In the embodiment, the substrate may be further arranged (e.g., placed) under the first electrode 110 or on the second electrode 190. The substrate may be a glass substrate or a plastic substrate, each having excellent (or suitable) mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and / or waterproofness.
[0437] The first electrode 110 may be formed by depositing and / 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.
[0438] 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 may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO) and a combination thereof, but not limited thereto. In various embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the material used to form the first electrode 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 a combination thereof, but not limited thereto.
[0439] 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.
[0440] Organic layer 150
[0441] The organic layer 150 may be disposed on the first electrode 110. The organic layer 150 may include a light emitting layer.
[0442] The organic layer 150 may further include a hole transport region between the first electrode 110 and the light emitting layer and an electron transport region between the light emitting layer and the second electrode 190 .
[0443] Hole transport region in the organic layer 150
[0444] The hole transport region may have i) a single-layer structure having a single layer including a single material, ii) a single-layer structure having a single layer including a plurality of different materials, or iii) a multi-layer structure having a plurality of layers including a plurality of different materials.
[0445] The hole transport region may include at least one layer selected from a hole injection layer (HIL), a hole transport layer (HTL), a light emitting auxiliary layer, and an electron blocking layer (EBL).
[0446] For example, the hole transport zone may have a single-layer structure including a single layer of a plurality of different materials, or a multilayer structure having a structure of hole injection layer / hole transport layer, hole injection layer / hole transport layer / luminescence auxiliary layer, hole injection layer / luminescence auxiliary layer, hole transport layer / luminescence auxiliary layer, or hole injection layer / hole transport layer / electron blocking layer, wherein for each structure, the constituent layers are sequentially stacked in the order described from the first electrode 110, but the structure of the hole transport zone is not limited thereto.
[0447] The hole transport region may include at least one selected from the group consisting of m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), a compound represented by Formula 201, and a compound represented by Formula 202:
[0448]
[0449] Formula 201
[0450]
[0451] Formula 202
[0452]
[0453] In equations 201 and 202,
[0454] L 201 To L 204 may 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 -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 a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0455] L 205 Can be selected from *-O-*', *-S-*', *-N(Q 201 )-*', substituted or unsubstituted C 1 -C 20 Alkylene groups, substituted or unsubstituted C 2 -C 20 Alkenylene, 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 a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0456] xa1 to xa4 may each independently be an integer selected from 0 to 3,
[0457] xa5 may be an integer selected from 1 to 10, and
[0458] R 201 To R 204and Q 201 may 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 a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
[0459] For example, R in Equation 202 201 and R 202 may optionally be linked to each other via a single bond, a dimethyl-methylene group or a diphenyl-methylene group; and R 203 and R 204 The groups may optionally be linked to one another via single bonds, dimethyl-methylene groups or diphenyl-methylene groups.
[0460] In various embodiments, in equations 201 and 202,
[0461] L 201 To L 205 Can be each independently selected from the group consisting of:
[0462] Phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthenylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenalenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylene, pyrenylene, chrysene, tetraphenylene, pyrenylene, perylene, pentaphenylene, and tetraphenylene. hexaphenylene, pentacene, rubidinylene, coronene, ovaphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilylene, and pyridylene; and
[0463] each selected from at least one substituted phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthenylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenalenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylene, pyrenylene, chrysene, tetraphenylene, pyrenylene, perylene, pentaphenylene, hexaphenylene, pentaphenylene , rubidinyl, corundum, phenylene, thienyl, furanyl, carbazolylene, indolyl, isoindolyl, benzofuranyl, benzothiophenylene, dibenzofuranyl, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilylene and pyridinylene: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C 1 -C 10 Alkyl substituted phenyl, phenyl substituted with -F, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, tetracenyl, phenanthrenyl, peryl, pentaphenyl, hexacenyl, pentacecenyl, rubenyl, coronenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, pyridyl, -Si(Q) 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32 ),
[0464] Where 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.
[0465] In various embodiments, xa1 to xa4 may each independently be 0, 1 or 2.
[0466] In various embodiments, xa5 can be 1, 2, 3 or 4.
[0467] In various embodiments, R 201 To R204 and Q 201 Can be each independently selected from the group consisting of:
[0468] phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, tetracenyl, phenanthrenyl, peryl, pentaphenyl, hexacenyl, pentacecenyl, rubenyl, coronenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilopentyl, and pyridinyl; and
[0469] each of which is selected from at least one substituted phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, tetracenyl, phenanthrenyl, peryl, pentaphenanthrenyl, hexacenyl, pentacene 1-Hydroxy, ... 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C 1 -C 10 Alkyl-substituted phenyl, phenyl substituted with -F alkyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, tetracenyl, phenanthrenyl, peryl, pentaphenyl, hexacenyl, pentacecenyl, rubenyl, coronenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, pyridyl, -Si(Q) 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32 ),
[0470] Where Q 31To Q 33 Same as described herein.
[0471] In various embodiments, R selected from Formula 201 201 To R 203 At least one of can be independently selected from the group consisting of:
[0472] fluorenyl, spiro-bifluorenyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl; and
[0473] Fluorenyl, spiro-bifluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl, each substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C 1 -C 10 alkyl-substituted phenyl, phenyl substituted by -F alkyl, naphthyl, fluorenyl, spiro-bifluorenyl, carbazolyl, dibenzofuranyl and dibenzothienyl,
[0474] However, the implementation mode is not limited thereto.
[0475] In various embodiments, in Formula 202, i) R 201 and R 202 can be connected to each other via a single bond and / or ii) R 203 and R 204 can be connected to each other via a single bond.
[0476] In various embodiments, R selected from Formula 202 201 To R 204 At least one of may be selected from the group consisting of:
[0477] carbazolyl; and
[0478] A carbazolyl group substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C 1 -C 10 alkyl-substituted phenyl, -F-substituted phenyl, naphthyl, fluorenyl, spiro-bifluorenyl, carbazolyl, dibenzofuranyl and dibenzothienyl,
[0479] However, the implementation mode is not limited thereto.
[0480] The compound represented by Formula 201 can be represented by Formula 201A:
[0481] Formula 201A
[0482]
[0483] In various embodiments, the compound represented by Formula 201 may be represented by Formula 201A(1), but is not limited thereto:
[0484] Formula 201A(1)
[0485]
[0486] In various embodiments, the compound represented by Formula 201 may be represented by Formula 201A-1, but is not limited thereto:
[0487] Formula 201A-1
[0488]
[0489] In various embodiments, the compound represented by Formula 202 may be represented by Formula 202A:
[0490] Formula 202A
[0491]
[0492] In various embodiments, the compound represented by Formula 202 may be represented by Formula 202A-1:
[0493] Formula 202A-1
[0494]
[0495] In Formulas 201A, 201A(1), 201A-1, 202A and 202A-1,
[0496] L 201 To L 203 , xa1 to xa3, xa5 and R 202 To R 204 The descriptions are the same as those provided herein,
[0497] R 211 and R 212 The descriptions are independent of each other and combined with R 203 Same description as provided,
[0498] R 213 To R217 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, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C 1 -C 10 Alkyl substituted phenyl, phenyl substituted with -F, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, tetracenyl, phenanthrenyl, peryl, pentaphenyl, hexacenyl, pentacecenyl, rubenyl, coronenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl and pyridinyl.
[0499] The hole transport region may include at least one compound selected from compounds HT1 to HT39, but is not limited thereto:
[0500]
[0501]
[0502]
[0503] The thickness of the hole transport region can be about to about For example, about to about When the hole transport region includes at least one of 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 For example, about to about and the thickness of the hole transport layer can be in the range of about to about For example, about to about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within any of these ranges, satisfactory (or suitable) hole transport characteristics can be obtained without significantly increasing the driving voltage.
[0504] The light-emitting auxiliary layer can increase the light-emitting efficiency of the device by compensating the optical resonance distance according to the wavelength of the light emitted by the light-emitting layer, and the electron blocking layer can block or reduce the flow of electrons from the electron transport region. The light-emitting auxiliary layer and the electron blocking layer can each include any material as described above.
[0505] p-type dopant
[0506] In addition to the materials described above, the hole transport region may also 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.
[0507] The charge generating material may be, for example, a p-type dopant.
[0508] In various embodiments, the p-type dopant may have a lowest unoccupied molecular orbital (LUMO) energy level of −3.5 eV or less.
[0509] The p-type dopant may include at least one selected from the group consisting of a quinone derivative, a metal oxide, and a cyano group-containing compound, but the embodiment is not limited thereto.
[0510] For example, the p-type dopant may include at least one selected from the group consisting of:
[0511] Quinone derivatives, such as tetracyanobenzoquinodimethane (TCNQ) and / or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanobenzoquinodimethane (F4-TCNQ);
[0512] Metal oxides, such as tungsten oxide and / or molybdenum oxide;
[0513] 1,4,5,8,9,11-Hexaazatriphenylene-hexacarbonitrile (HAT-CN); and
[0514] The compound represented by formula 221,
[0515] But it is not limited to this:
[0516]
[0517] Formula 221
[0518]
[0519] In formula 221,
[0520] R 221 To R 223 may be independently selected from 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 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, and substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, wherein R is selected from 221 To R 223 At least one of the following may have at least one substituent selected from the group consisting of cyano, -F, -Cl, -Br, -I, C substituted with -F 1 -C 20 Alkyl, C substituted by -Cl 1 -C 20 Alkyl, C substituted by -Br 1 -C 20 Alkyl and C substituted by -I 1 -C 20 alkyl.
[0521] The light emitting layer in the organic layer 150
[0522] When the organic light-emitting device 10 is a full-color organic light-emitting device, the light-emitting layer may be patterned into a red light-emitting layer, a green light-emitting layer, and / or a blue light-emitting layer according to each sub-pixel. In various embodiments, the light-emitting layer may have a stacked structure of two or more layers selected from a red light-emitting layer, a green light-emitting layer, and a blue light-emitting layer, wherein the two or more layers may contact each other or may be separated from each other. In various embodiments, the light-emitting layer may include two or more materials selected from a red light-emitting material, a green light-emitting material, and a blue light-emitting material, wherein two or more materials may be mixed with each other in a single layer to emit white light.
[0523] In various embodiments, the light-emitting layer of the organic light-emitting device 10 may be a first color light-emitting layer, and
[0524] The organic layer may further include at least one second color light emitting layer,
[0525] The first color light and the second color light may be the same or different from each other, and
[0526] The first color light and the second color light may be emitted as mixed light.
[0527] Herein, when the first color light is different from the second color light, the maximum brightness wavelength of the first color light is different from the maximum brightness wavelength of the second color light.
[0528] For example, the mixed light may be white light, but is not limited thereto.
[0529] In various embodiments, the light-emitting layer of the organic light-emitting device 10 may be a first color light-emitting layer, and
[0530] The organic layer may further include at least one second color light emitting layer and at least one third color light emitting layer.
[0531] The first color light, the second color light and the third color light may be the same or different from each other, and
[0532] The first color light, the second color light, and the third color light may be emitted as mixed light.
[0533] Herein, when the first color light, the second color light, and the third color light are different from each other, the maximum brightness wavelength of the first color light, the maximum brightness wavelength of the second color light, and the maximum brightness wavelength of the third color light are different from each other.
[0534] For example, the mixed light may be white light, but is not limited thereto.
[0535] The light emitting layer may include a host and a dopant. The dopant may include at least one selected from a phosphorescent dopant and a fluorescent dopant.
[0536] The amount of the dopant in the light emitting layer may be, for example, in the range of about 0.01 to about 15 parts by weight based on 100 parts by weight of the host, but is not limited thereto.
[0537] The thickness of the light-emitting layer can be about to about For example, about to about When the thickness of the light-emitting layer is within any of these ranges, excellent (or suitable) light-emitting characteristics can be obtained without significantly increasing the driving voltage.
[0538] Subject in the luminous layer
[0539] The host may include a first compound represented by Formula 1.
[0540] In various embodiments, the host may include a first compound represented by Formula 1 and may further include a compound represented by the following Formula 301.
[0541] In various embodiments, the light emitting layer includes a first host and a second host,
[0542] The first host may be a first compound, and
[0543] The first body may be different from the second body, but the embodiment is not limited thereto.
[0544] Formula 301
[0545] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 .
[0546] In formula 301,
[0547] Ar 301 It can be substituted or unsubstituted C 5 -C 60 A carbocyclic group or a substituted or unsubstituted C 1 -C 60 Heterocyclic groups,
[0548] xb11 can be 1, 2 or 3,
[0549] 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 a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0550] xb1 may be an integer selected from 0 to 5,
[0551] R 301 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 10Cycloalkyl, 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 fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 301 )(Q 302 )(Q 303 )、-N(Q 301 )(Q 302 )、-B(Q 301 )(Q 302 )、-C(=O)(Q 301 )、-S(=O) 2 (Q 301 ) and -P(=O)(Q 301 )(Q 302 ),and
[0552] xb21 may be an integer selected from 1 to 5,
[0553] Where 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 embodiment is not limited thereto.
[0554] In various embodiments, Ar in Formula 301 301 You can choose from the group consisting of:
[0555] naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, naphthacene, phenanthrenyl, peryl, pentaphenanthrenyl, indenoanthryl, dibenzofuranyl, and dibenzothiophenyl; and
[0556] naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, tetracenyl, phenanthrenyl, peryl, pentaphenanthrenyl, indenoanthryl, dibenzofuranyl and dibenzothienyl, each of which is selected from at least one substituted
[0557] Each is selected from 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 substituted naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, naphthacene, phenanthrenyl, peryl, pentaphenanthrenyl, indenoanthryl, dibenzofuranyl and dibenzothienyl,
[0558] Where Q 31 To Q 33 Each 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 embodiment is not limited thereto.
[0559] When xb11 in Formula 301 is 2 or greater, two or more Ar 301 can be connected to each other via a single bond.
[0560] In various embodiments, the compound represented by Formula 301 may be represented by Formula 301-1 or 301-2:
[0561] Formula 301-1
[0562]
[0563] Formula 301-2
[0564]
[0565] Wherein in formulas 301-1 to 301-2,
[0566] A 301 To A 304 The phenyl group may be independently selected from phenyl, naphthyl, phenanthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, pyridyl, pyrimidyl, indenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, indolyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, furanyl, benzofuranyl, dibenzofuranyl, naphthofuranyl, benzonaphthofuranyl, dinaphthofuranyl, thienyl, benzothienyl, dibenzothienyl, naphthothienyl, benzonaphthothienyl and dinaphthothienyl,
[0567] X 301 Can be O, S or N-[(L 304 ) xb4 -R 304 ],
[0568] 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 ),
[0569] xb22 and xb23 can each independently be 0, 1 or 2,
[0570] L 301 、xb1、R 301 and Q 31 To Q 33 The descriptions may be the same as those provided above,
[0571] L 302 To L 304 The description can be combined with L 301 The same ones provided,
[0572] The descriptions of xb2 to xb4 may each independently be the same as the description provided in conjunction with xb1,
[0573] R 302 To R 304 The descriptions can be combined with R 301 Same description provided.
[0574] For example, L in equations 301, 301-1, and 301-2 301 To L 304 Can be each independently selected from the group consisting of:
[0575] Phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, phenylphenanthrenylene, pyrenylene, chrysene, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene , isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridinylene, imidazopyrimidinylene, and azacarbazolylene; and
[0576] each of which is selected from at least one substituted phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, phenylphenanthrenylene, pyrenylene, chrysene, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilylene, pyridinylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene 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: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazinyl, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, peryl, pentaphenyl, hexacenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, pyridyl, imidazolyl, pyrazole , 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, 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),
[0577] Where Q 31 To Q 33 Same as described herein.
[0578] In various embodiments, R in Formulas 301, 301-1, and 301-2 301 To R 304 Can be each independently selected from the group consisting of:
[0579] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, peryl, pentaphenyl, hexacenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, 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
[0580] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, 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: 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, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, peryl, pentaphenyl, hexacenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, pyridyl, imidazolyl, pyrazole , 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, 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 ),
[0581] Where Q 31 To Q 33 Same as described herein.
[0582] In various 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.
[0583] The host may include at least one selected from the group consisting of 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 are not limited thereto:
[0584]
[0585]
[0586]
[0587] The phosphorescent dopant included in the light emitting layer in the organic layer 150
[0588] The phosphorescent dopant may include an organic metal complex represented by the following Formula 401:
[0589] Formula 401
[0590] M(L 401 ) xc1 (L 402 ) xc2 .
[0591] Formula 402
[0592]
[0593] In equations 401 and 402,
[0594] 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),
[0595] L 401 A ligand represented by formula 402 may be selected, and xc1 may be 1, 2 or 3, wherein when xc1 is 2 or greater, two or more L 401 can be the same or different from each other,
[0596] L 402 may be an organic ligand, and xc2 may be an integer selected from 0 to 4, wherein when xc2 is 2 or greater, two or more L 402 can be the same or different from each other,
[0597] X 401 To X 404 may each independently be nitrogen or carbon,
[0598] X 401 and X 403 can be connected to each other via single bonds or double bonds, and X 402 and X 404 can be linked to each other via single or double bonds,
[0599] A 401 and A 402 Can be independently C 5 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic groups,
[0600] X 405It 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(Q 411 )=*', 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,
[0601] X 406 Can be a single bond, O or S,
[0602] 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 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 fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q401 )(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,
[0603] xc11 and xc12 may each independently be an integer selected from 0 to 10, and
[0604] * and *' in Formula 402 each independently indicate a binding site with M in Formula 401.
[0605] In various embodiments, A in equation 402 401 and A 402 The benzofuranyl, benzothiophene, benzoxazolyl, isobenzothiophene, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, and dibenzothiophene may be independently selected from the group consisting of phenyl, naphthyl, fluorenyl, spiro-bifluorenyl, indenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, benzimidazolyl, benzofuranyl, benzothiophene, isobenzothiophene, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, and dibenzothiophene.
[0606] In various embodiments, in formula 402, i) X 401 can be nitrogen and X 402 may be carbon, or ii) X 401 and X 402 Both may be nitrogen.
[0607] In various embodiments, R in equation 402 401 and R 402 Can be each independently selected from the group consisting of:
[0608] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy;
[0609] Each of the following C 1 -C 20 Alkyl and C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazine, hydrazone, phenyl, naphthyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl and norbornenyl;
[0610] Cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl;
[0611] cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl, each substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, adamantyl, norbornyl, norbornenyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, dibenzofuranyl, and dibenzothiophenyl; and
[0612] -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 ),
[0613] Where Q 401 To Q 403 Can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10alkoxy, phenyl, biphenyl, and naphthyl, but the embodiment is not limited thereto.
[0614] In various embodiments, when xc1 in Formula 401 is 2 or greater, two or more L 401 Two Aces 401 Optionally, the 407 Connect to each other, or two A 402 Can be linked via the linker group X 408 are linked to each other (see, e.g., compounds PD1 to PD4 and PD7 below). 407 and X 408 can be each independently a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 413 )-*'、*-C(Q 413 )(Q 414 )-*', or *-C(Q 413 )=C(Q 414 )-*'(where Q 413 and Q 414 can be independently hydrogen, deuterium, C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, phenyl, biphenyl, terphenyl or naphthyl), but is not limited thereto.
[0615] L in Formula 401 402 It can be any suitable monovalent, divalent or trivalent organic ligand. For example, L 402 It may be selected from halogen ligands, diketone ligands (eg, acetylacetonate), carboxylic acid ligands (eg, picolinate), -C(=O), isonitrile, -CN, and phosphorus ligands (eg, phosphine and / or phosphite), but is not limited thereto.
[0616] In various embodiments, the phosphorescent dopant may be selected from, for example, compounds PD1 to PD25, but are not limited thereto:
[0617]
[0618]
[0619] Fluorescent dopants in the light-emitting layer
[0620] The fluorescent dopant may include an arylamine compound or a styrylamine compound.
[0621] The fluorescent dopant may include a compound represented by the following Formula 501:
[0622] Formula 501
[0623]
[0624] In formula 501,
[0625] Ar 501 It can be substituted or unsubstituted C 5 -C 60 A carbocyclic group or a substituted or unsubstituted C 1 -C 60 Heterocyclic groups,
[0626] L 501 To L 503 may 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 -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 a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0627] xd1 to xd3 may each independently be an integer selected from 0 to 3,
[0628] R 501 To R 502 may 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 60heteroaryl, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and
[0629] xd4 may be an integer selected from 1 to 6.
[0630] In various embodiments, Ar in Formula 501 501 You can choose from the group consisting of:
[0631] naphthyl, heptalenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, naphthacene, phenanthrenyl, perylenyl, pentaphenanthrenyl, indenoanthryl, and indenophenanthrenyl; and
[0632] each of which is selected from at least one substituted naphthyl, heptalenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, naphthacene, phenanthrenyl, peryl, pentaphenanthrenyl, indenoanthryl and indenophenanthrenyl: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.
[0633] In various embodiments, L in Formula 501 501 To L 503 Can be each independently selected from the group consisting of:
[0634] phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, phenylphenanthrenylene, pyrenylene, chrysene, perylene, pentaphenylene, hexaphenylene, pentaphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzoheterosilacyclopentadienylene, and pyridinylene; and
[0635] phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, phenylphenanthrenylene, pyrenylene, chrysene, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzoheterosilacyclopentadienylene and pyridylene, each of which is substituted with at least one selected from the group consisting of 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, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, peryl, pentaphenanthrenyl, hexacenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl and pyridyl.
[0636] In various embodiments, R in Formula 501 501 and R 502 Can be each independently selected from the group consisting of:
[0637] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, peryl, pentaphenanthrenyl, hexacenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl, and pyridyl; and
[0638] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, peryl, pentaphenanthrenyl, hexacenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl and pyridyl, each substituted with at least one selected from the group consisting of 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, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, peryl, pentaphenanthrenyl, hexacenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, pyridyl and -Si(Q) 31 )(Q 32 )(Q 33 ),
[0639] Where 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.
[0640] In various implementations, xd4 in formula 501 may be 2, but is not limited thereto.
[0641] For example, the fluorescent dopant may be selected from compounds FD1 to FD22:
[0642]
[0643]
[0644]
[0645] In various embodiments, the fluorescent dopant may be selected from the compounds shown below, but is not limited thereto:
[0646] Electron transport region in the organic layer 150
[0647] The electron transport region may have i) a single-layer structure having a single layer including a single material, ii) a single-layer structure having a single layer including a plurality of different materials, or iii) a multi-layer structure having a plurality of layers including a plurality of different materials.
[0648] 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 is not limited thereto.
[0649] For example, the electron transport region may have a structure of an electron transport layer / electron injection layer, a structure of a hole blocking layer / electron transport layer / electron injection layer, a structure of an electron control layer / electron transport layer / electron injection layer, or a structure of a buffer layer / electron transport layer / electron injection layer, wherein in each of these structures, the constituent layers are sequentially stacked in this order from the light emitting layer. However, the structure of the electron transport region is not limited thereto.
[0650] The electron transport region (eg, a buffer layer, a hole blocking layer, an electron control layer, and / or an electron transport layer in the electron transport region) may include a metal-free compound containing at least one nitrogen-containing ring that is depleted of π electrons.
[0651] As used herein, the term "π-electron-depleted nitrogen-containing ring" refers to a C- 1 -C 60 Heterocyclic group.
[0652] For example, the “π-electron-depleted nitrogen-containing ring” may be i) a 5-membered to 7-membered heteromonocyclic group having at least one *-N=*' portion, ii) a heteropolycyclic group in which two or more 5-membered to 7-membered heteromonocyclic groups, each having at least one *-N=*' portion, are condensed (e.g., fused), or iii) a heteropolycyclic group in which two or more 5-membered to 7-membered heteromonocyclic groups, each having at least one *-N=*' portion, are condensed (e.g., fused). 5 -C 60 A carbocyclic group is a condensed (eg, fused) heteropolycyclic group.
[0653] Examples of nitrogen-containing rings depleted of π electrons include 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, but are not limited thereto.
[0654] For example, the electron transport region may include a compound represented by Formula 601 (described below).
[0655] For example, the electron transport region (eg, a buffer layer, a hole blocking layer, an electron control layer, and / or an electron transport layer in the electron transport region) may include the second compound represented by Formula 2.
[0656] For example, the electron transport region (eg, a buffer layer, a hole blocking layer, an electron control layer, and / or an electron transport layer in the electron transport region) may include a first compound represented by Formula 1 and a second compound represented by Formula 2.
[0657] In various embodiments, the electron transport region may include a first layer, and the first layer may include the second compound represented by Formula 2, but the embodiments are not limited thereto. In this regard, the first layer may be an electron transport layer.
[0658] In various embodiments, the electron transport region may include a first layer and a second layer, the first layer being between the light emitting layer and the second layer, and the first layer may include a second compound represented by Formula 2, but the embodiments are not limited thereto. In this regard, the first layer may be a buffer layer, and the second layer may be an electron transport layer.
[0659] In various embodiments, the electron transport region may include a first layer and a second layer, the first layer being between the light emitting layer and the second layer, and the first layer may include a first compound represented by Formula 1 and the second layer may include a second compound represented by Formula 2, but the embodiments are not limited thereto. In this regard, the first layer may be a buffer layer, and the second layer may be an electron transport layer.
[0660] In various embodiments, the electron transport region may include a first layer and a second layer, the first layer is between the light emitting layer and the second layer, the first layer may include a second compound represented by Formula 2, the second layer may include a second compound represented by Formula 2, and the second compound included in the first layer may be different from the second compound included in the second layer, but the embodiments are not limited thereto. In this regard, the first layer may be a buffer layer, and the second layer may be an electron transport layer.
[0661] The electron transport region may further include a compound represented by Formula 601 in addition to the second compound represented by Formula 2, or in addition to the first compound represented by Formula 1 and the second compound represented by Formula 2.
[0662] Formula 601
[0663] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .
[0664] In formula 601,
[0665] Ar 601 It can be substituted or unsubstituted C 5 -C 60 A carbocyclic group or a substituted or unsubstituted C 1 -C60 Heterocyclic groups,
[0666] xe11 can be 1, 2 or 3,
[0667] 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 a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0668] xe1 may be an integer selected from 0 to 5,
[0669] 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 fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 601 )(Q 602 )(Q 603 )、-C(=O)(Q 601 )、-S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ),
[0670] Where Q 601 To Q 603 Can be independently C 1 -C 10 Alkyl, C 1 -C 10 alkoxy, phenyl, biphenyl, terphenyl or naphthyl, and
[0671] xe21 may be an integer selected from 1 to 5.
[0672] In various embodiments, the amount of Ar 601 and / or xe21 number of R 601 A pi-electron depleted nitrogen-containing ring as described herein may be included.
[0673] In various embodiments, Ar in Formula 601 601 You can choose from the group consisting of:
[0674] Phenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, naphthacene, phenanthrenyl, peryl, 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
[0675] each of which is selected from at least one substituted phenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, naphthacene, phenanthrenyl, peryl, peryl, pentaphenyl, indenoanthryl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indazolyl, purinyl, quinoline quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C20 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 ),
[0676] Where 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.
[0677] When xe11 in Formula 601 is 2 or greater, two or more Ar 601 can be connected to each other via a single bond.
[0678] In various embodiments, Ar in Formula 601 601 It may be anthracene.
[0679] In various embodiments, the compound represented by Formula 601 can be represented by Formula 601-1:
[0680] Formula 601-1
[0681]
[0682] In formula 601-1,
[0683] 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 selected from X 614 to x 616 At least one of may be N,
[0684] L 611 To L 613 The description can be combined with L 601 Same description as provided,
[0685] The descriptions of xe611 to xe613 may each independently be the same as the description provided in conjunction with xe1.
[0686] R611 To R 613 The descriptions can be combined with R 601 Same description as provided,
[0687] 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.
[0688] In various embodiments, L in equations 601 and 601-1 601 and L 611 To L 613 Can be each independently selected from the group consisting of:
[0689] Phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, phenylphenanthrenylene, pyrenylene, chrysene, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilylene, pyridylene, imidazolylene, pyrazolylene, thiazolylene , isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, isobenzothiazolylene, benzoxazolylene, isobenzoxazolylene, triazolylene, tetrazolylene, imidazopyridinylene, imidazopyrimidinylene, and azacarbazolylene; and
[0690] each of which is selected from at least one substituted phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, phenylphenanthrenylene, pyrenylene, chrysene, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilylene, pyridinylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene 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: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazinyl, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, peryl, pentaphenyl, hexacenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, 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,
[0691] However, the implementation mode is not limited thereto.
[0692] In various embodiments, xe1 and xe611 to xe613 in Formulas 601 and 601-1 may each independently be 0, 1, or 2.
[0693] In various embodiments, R in Formula 601 and 601-1 601 and R 611 To R 613Can be each independently selected from the group consisting of:
[0694] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, pyridyl, imidazolyl, pyrazole oxazolyl, isoxazolyl, 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;
[0695] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, 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: 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, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, peryl, pentaphenyl, hexacenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, pyridyl, imidazolyl, pyridine oxazolyl, 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
[0696] -S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ),
[0697] Where Q 601 and Q 602 Same as described herein.
[0698] The electron transport region may include at least one compound selected from compounds ET1 to ET36, but is not limited thereto:
[0699]
[0700]
[0701]
[0702] In various embodiments, the electron transport region may include at least one selected from the group consisting of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq 3 , BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ) and NTAZ:
[0703]
[0704] The thickness of the buffer layer, the hole blocking layer and / or the electron control layer may be independently about to about For example, about to about When the thicknesses of the buffer layer, the hole blocking layer, and the electron control layer are within any of these ranges, the electron transport region may have excellent (or suitable) hole blocking characteristics and / or electron control characteristics without significantly increasing the driving voltage.
[0705] The thickness of the electron transport layer can be about to about For example, about to about When the thickness of the electron transport layer is within any range described above, the electron transport layer can have satisfactory (or suitable) electron transport characteristics without significantly increasing the driving voltage.
[0706] 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.
[0707] 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 independently selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiphenyloxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but is not limited thereto.
[0708] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (8-hydroxyquinoline lithium, LiQ) and / or compound ET-D2:
[0709]
[0710] 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 directly contact the second electrode 190.
[0711] The electron injection layer may have i) a single-layer structure having a single layer including a single material, ii) a single-layer structure having a single layer including a plurality of different materials, or iii) a multi-layer structure having a plurality of layers including a plurality of different materials.
[0712] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or a combination thereof.
[0713] The alkali metal may be selected from Li, Na, K, Rb, and Cs. In various embodiments, the alkali metal may be Li, Na, or Cs. In various embodiments, the alkali metal may be Li or Cs, but is not limited thereto.
[0714] The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.
[0715] The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, Gd, and Tb.
[0716] The alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound may be selected from oxides and halides (e.g., fluorides, chlorides, bromides, and / or iodides) of the alkali metal, the alkaline earth metal, and the rare earth metal, respectively.
[0717] 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 various embodiments, the alkali metal compound may be selected from LiF, Li 2 O, NaF, LiI, NaI, CsI, and KI, but is not limited thereto.
[0718] The alkaline earth metal compound may be selected from, for example, BaO, SrO, CaO, Ba x Sr 1-x O (0 < x < 1), and Ba x Ca 1-x O (0 < x < 1). In various embodiments, the alkaline earth metal compound may be selected from BaO, SrO, and CaO, but is not limited thereto.
[0719] The rare earth metal compound may be selected from YbF 3 、ScF 3 、ScO 3 、Y 2 O 3 、Ce 2 O 3 、GdF 3 和TbF 3 。 In various embodiments, the rare earth metal compound may be selected from YbF 3 、ScF 3 、TbF 3 、YbI3 ScI 3 and TbI 3 , but it is not limited to this.
[0720] The alkali metal complex, alkaline earth metal complex and rare earth metal complex may respectively include ions of alkali metal, ions of alkaline earth metal or ions of rare earth metal as described above, and the ligands coordinated with the ions of the alkali metal complex, alkaline earth metal complex and rare earth metal complex may each be independently selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiphenyloxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline and cyclopentadiene, but are not limited thereto.
[0721] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex or a combination thereof as described above. In various embodiments, the electron injection layer may also include an organic material. When the electron injection layer also includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex or a combination thereof may be uniformly or non-uniformly dispersed in a substrate including an organic material.
[0722] The thickness of the electron injection layer can be about to about For example, about to about When the thickness of the electron injection layer is within any range described above, the electron injection layer can have satisfactory (or suitable) electron injection characteristics without significantly increasing the driving voltage.
[0723] The second electrode 190
[0724] The second electrode 190 may be arranged (e.g., placed) on the organic layer 150 having the structure according to an embodiment of the present disclosure. The second electrode 190 may be a cathode (which is an electron injection electrode), and in this regard, a material for forming the second electrode 190 may be selected from metals, alloys, conductive compounds, and mixtures thereof, which have a relatively low work function.
[0725] In some embodiments, the second electrode 190 may include at least one selected from the group consisting of 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 is not limited thereto. The second electrode 190 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
[0726] The second electrode 190 may have a single-layer structure, or a multi-layer structure including two or more layers.
[0727] Figures 2 to 4 Description
[0728] Figure 2 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 in the order described; Figure 3 The organic light emitting device 30 includes a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220, which are sequentially stacked in the order recited; and Figure 4 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, which are sequentially stacked in the recited order.
[0729] At once Figures 2 to 4 By reference to Figure 1 The description thereof is presented to understand the description of the first electrode 110 , the organic layer 150 , and the second electrode 190 .
[0730] In the organic layer 150 of each of the organic light-emitting devices 20 and 40, light generated in the light-emitting layer can pass through the first electrode 110 (which can be a semi-transmissive electrode or a transmissive electrode) and the first capping layer 210 to the outside; and in the organic layer 150 of each of the organic light-emitting devices 30 and 40, light generated in the light-emitting layer can pass through the second electrode 190 (which can be a semi-transmissive electrode or a transmissive electrode) and the second capping layer 220 to the outside.
[0731] The first capping layer 210 and the second capping layer 220 may increase the external light emitting efficiency of the device according to the principle of constructive interference.
[0732] 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.
[0733] At least one selected from the first capping layer 210 and the second capping layer 220 may include at least one material selected from the following: carbocyclic compounds, heterocyclic compounds, amine-based compounds, porphyrin derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal-based complexes, and alkaline earth metal-based complexes. The carbocyclic compounds, heterocyclic compounds, and amine-based compounds may each be optionally substituted with a substituent containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In various embodiments, at least one selected from the first capping layer 210 and the second capping layer 220 may include an amine-based compound.
[0734] In one embodiment, at least one selected from the first capping layer 210 and the second capping layer 220 may include the compound represented by Formula 201 or the compound represented by Formula 202.
[0735] In various embodiments, at least one selected from the first capping layer 210 and the second capping layer 220 may include a compound selected from compounds HT28 to HT33 and compounds CP1 to CP5, but is not limited thereto:
[0736]
[0737] In the above, it has been combined Figures 1 to 4 The organic light emitting device according to the embodiment of the present disclosure is described. However, the embodiment of the present disclosure is not limited thereto.
[0738] The layer constituting the hole transport region, the light emitting layer, and the layer constituting the electron transport region can each be independently formed in a specific region by using one or more suitable methods, such as vacuum deposition, spin coating, casting, Langmuir-blodgett (LB) deposition, inkjet printing, laser printing, and / or laser induced thermal imaging.
[0739] When the layer constituting the hole transport region, the light emitting layer, and the layer constituting the electron transport region are each independently formed by vacuum deposition, for example, by considering the compound included in each layer to be formed, and the structure of each layer to be formed, the vacuum deposition can be carried out at a deposition temperature of about 100 to about 500° C., at a temperature of about 10 -8 to about 10 -3 Torr and a vacuum of about 0.01 to about The deposition rate is 2.5 ~ 10 s.
[0740] When a layer constituting a hole transport region, a light-emitting layer, and a layer constituting an electron transport region are each independently formed by spin coating, for example, by considering the compound included in each layer to be formed, and the structure of each layer to be formed, the spin coating can be performed at a coating rate of about 2,000 rpm to about 5,000 rpm and at a heat treatment temperature of about 80°C to 200°C.
[0741] General Definition of Substituents
[0742] The term "C 1 -C 60 "Alkyl" may refer to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and non-limiting examples thereof are methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl. The term "C 1 -C 60 "Alkylene group" refers to a group having 1 -C 60 Alkyl is a divalent group of the same structure.
[0743] The term "C 2 -C 60 "Alkenyl" may refer to 2 -C 60 One or more positions of the hydrocarbon chain of the alkyl group (e.g., at C 2 -C 60 The term "C" as used herein refers to a hydrocarbon group having at least one carbon-carbon double bond (in the middle or at either end of the alkyl group), and limiting examples thereof may include ethenyl, propenyl, and butenyl. 2 -C 60 "Alkenylene" refers to a group having substantially the same 2 -C 60 Alkenyl is a divalent group of the same structure.
[0744] The term "C 2 -C 60 "Alkynyl" may refer to 2 -C 60 One or more positions of the hydrocarbon chain of the alkyl group (e.g., at C 2 -C 60 The term "C" as used herein refers to a hydrocarbon group having at least one carbon-carbon triple bond (in the middle or at either end of an alkyl group), and non-limiting examples thereof may include ethynyl and propynyl. 2 -C 60 "Alkyne" may refer to a 2 -C 60 Alkynyl is a divalent group of the same structure.
[0745] The term "C1 -C 60 "Alkoxy" may refer to -OA 101 The monovalent group represented by 101 C 1 -C 60 alkyl), and non-limiting examples thereof include methoxy, ethoxy, and isopropoxy.
[0746] The term "C 3 -C 10 "Cycloalkyl" may refer to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. As used herein, "Cycloalkyl" may refer to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. 3 -C 10 "Cycloalkylene" may refer to a 3 -C 10 Cycloalkyl is a divalent group of the same structure.
[0747] The term "C 1 -C 10 The term "heterocycloalkyl" as used herein may refer to a monovalent 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 are tetrahydrofuranyl and tetrahydrothienyl. 1 -C 10 "Heterocycloalkylene" may refer to a 1 -C 10 Heterocycloalkyl is a divalent group of the same structure.
[0748] The term "C 3 -C 10 The term "cycloalkenyl" as used herein may refer to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one double bond in its ring and not having aromaticity, and non-limiting examples thereof are cyclopentenyl, cyclohexenyl and cycloheptenyl. 3 -C 10 "Cycloalkenylene" may refer to a 3 -C 10 Cycloalkenyl is a divalent group of the same structure.
[0749] The term "C 1 -C 10 The term "heterocycloalkenyl group" may refer to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom, 1 to 10 carbon atoms and at least one double bond in its ring. 1 -C 10Non-limiting examples of heterocycloalkenyl are 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl and 2,3-dihydrothienyl. 1 -C 10 "Heterocycloalkenylene" may refer to a 1 -C 10 Heterocycloalkenyl is a divalent group of the same structure.
[0750] The term "C 6 -C 60 "Aryl" may refer to a monovalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms, and the C 6 -C 60 The arylene group may refer to a divalent group having an aromatic system containing 6 to 60 carbon atoms. 6 -C 60 Non-limiting examples of aryl groups are phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl and chrysene. 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 to each other.
[0751] The term "C 1 -C 60 The term "heteroaryl" may refer to a monovalent group having a carbocyclic aromatic system having at least one heteroatom selected from N, O, Si, P and S as a ring atom and 1 to 60 carbon atoms. 1 -C 60 The heteroarylene group may refer to a divalent group having an aromatic system having at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom and 1 to 60 carbon atoms. 1 -C 60 Non-limiting examples of heteroaryl are pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl and isoquinolinyl. 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene groups each independently include two or more rings, the respective rings may be fused to each other.
[0752] The term "C 6 -C 60 "Aryloxy" may refer to 102 The monovalent group represented by 102 C 6 -C 60 aryl), and the term "C6 -C 60 "Arylthio" may refer to -SA 103 The monovalent group represented by 103 C 6 -C 60 aryl).
[0753] The term "monovalent non-aromatic fused polycyclic group" as used herein may refer to a monovalent group having two or more rings condensed (e.g., fused) to each other, having only carbon atoms as ring-forming atoms (e.g., 8 to 60 carbon atoms) and being non-aromatic (e.g., not having overall aromaticity) in the entire molecular structure. A non-limiting example of a monovalent non-aromatic fused polycyclic group is a fluorenyl group. The term "divalent non-aromatic fused polycyclic group" as used herein may refer to a divalent group having the same structure as a monovalent non-aromatic fused polycyclic group.
[0754] The term "monovalent non-aromatic fused heteropolycyclic group" as used herein may refer to a monovalent group having two or more rings condensed (e.g., fused) to each other, having at least one heteroatom selected from N, O, Si, P, and S other than carbon atoms (e.g., 1 to 60 carbon atoms) as a ring-forming atom and having no aromaticity in the entire molecular structure (e.g., not having overall aromaticity). A non-limiting example of a monovalent non-aromatic fused heteropolycyclic group is a carbazolyl group. The term "divalent non-aromatic fused heteropolycyclic group" as used herein may refer to a divalent group having the same structure as a monovalent non-aromatic fused heteropolycyclic group.
[0755] The term "C 5 -C 60 A "carbocyclic group" may refer to a monocyclic or polycyclic group having 5 to 60 carbon atoms, wherein the ring atoms are only carbon atoms. 5 -C 60 The carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. 5 -C 60 The carbocyclic group can be a ring (such as phenyl), a monovalent group (such as phenyl) or a divalent group (such as phenylene). 5 -C 60 The number of substituents attached to the carbocyclic group, C 5 -C 60 The carbocyclic group may be a trivalent group or a tetravalent group.
[0756] The term "C 1 -C 60 "Heterocyclic group" refers to a group having 5 -C 60The carbocyclic group is a group of the same structure except that at least one heteroatom selected from N, O, Si, P and S is used as a ring-forming atom in addition to carbon (for example, the number of carbon atoms may range from 1 to 60).
[0757] The term "C 6 -C 60 The term "aromatic hydrocarbon group" may refer to an aromatic monocyclic or polycyclic group having 6 to 60 carbon atoms, wherein the ring atoms are only carbon atoms. 6 -C 60 The aromatic hydrocarbon group can be a ring (such as phenyl), a monovalent group (such as phenyl) or a divalent group (such as phenylene). In various embodiments, depending on the C 6 -C 60 The number of substituents attached to the aromatic hydrocarbon group, C 6 -C 60 The aromatic hydrocarbon group may be a trivalent group or a tetravalent group.
[0758] The term "C 1 -C 60 "Heteroaromatic group" may refer to a 6 -C 60 The aromatic hydrocarbon group is a group of the same structure except that at least one heteroatom selected from N, O, Si, P and S is used as a ring-forming atom in addition to carbon atoms (for example, the number of carbon atoms may range from 1 to 60).
[0759] As used herein, substituted C 1 -C 60 Alkylene groups, substituted C 2 -C 60 Alkenylene, substituted C 2 -C 60 Alkynylidene, 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 C2 -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 of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group may be selected from the group consisting of:
[0760] Deuterium (-D), -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;
[0761] Each of the following C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy: 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 60Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 ) and -P(=O)(Q 11 )(Q 12 );
[0762] 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 fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups;
[0763] Each of the following 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 fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C1 -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 fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 ) and -P(=O)(Q 21 )(Q 22 );as well as
[0764] -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 ),
[0765] Where Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33can 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, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group.
[0766] 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" used herein may refer to methoxy, and "D" used herein may refer to deuterium.
[0767] The term "biphenyl" as used herein may refer to a monovalent group in which two benzene rings are connected to each other via a single bond. For example, a "biphenyl" may be a "phenyl substituted with a phenyl group". A "biphenyl" may also be a group having "C 6 -C 60 "substituted phenyl" having "aryl" as a substituent.
[0768] The term "terphenyl" as used herein may refer to a monovalent group in which adjacent benzenes are connected to each other via a single bond. For example, "terphenyl" may be a "phenyl substituted with biphenyl". "Terphenyl" may also be a "substituted phenyl" having a "phenyl substituted with C 6 -C 60 Aryl substituted C 6 -C 60 "Aryl" as a substituent.
[0769] Unless otherwise defined, * and *' used herein each independently refer to a binding site to an adjacent atom in the corresponding formula.
[0770] Hereinafter, the compounds according to the embodiments of the present disclosure and the organic light-emitting devices according to the embodiments will be described in more detail with reference to the examples. However, these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. The expression "using B instead of A" used in describing the examples may refer to using an equivalent molar equivalent of B to replace a molar equivalent of A.
[0771] Example
[0772]
[0773] Example 1-1
[0774] The anode was prepared by cutting a glass substrate, and ITO was deposited on the substrate. The thickness of the glass substrate (anode) was 50 mm x 50 mm x 0.4 mm, and the glass substrate (anode) was ultrasonically cleaned with isopropyl alcohol and pure water (10 minutes each), and then the glass substrate (anode) was exposed to UV light radiation (10 minutes) and ozone for cleaning. Then, the obtained glass substrate (anode) was loaded onto a vacuum deposition device.
[0775] The compound m-MTDTA was vacuum-deposited on a glass substrate (anode) to form a Then, compound HT3 is vacuum-deposited on the hole injection layer to form a hole injection layer having a thickness of A hole transport layer with a thickness of 1000 Å is formed to form a hole transport region.
[0776] Compound 1-1 (as a host) and compound PD13 (as a dopant) were co-deposited on the hole transport region at a weight ratio of 95:5 to form a Thickness of the luminous layer.
[0777] Compound 2-38 is deposited on the light-emitting layer to form a Then, LiF is deposited on the electron transport layer to form an electron transport layer having a thickness of Then, Al is vacuum-deposited on the electron transport region to form a A cathode with a thickness of 100 nm is formed, thereby completing the manufacture of the organic light-emitting device.
[0778] Examples 1-2 to 1-4 and Comparative Examples 1-1 to 1-3
[0779] An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Example 1, except that in forming the light-emitting layer and the electron transport layer, the compounds listed in Table 1 were used instead of Compounds 1-1 and 2-38, respectively.
[0780] Table 1
[0781]
[0782]
[0783] Example 2-1
[0784] The anode was prepared by cutting a glass substrate, and ITO was deposited on the substrate. The thickness of the glass substrate (anode) was 50 mm x 50 mm x 0.4 mm, and the glass substrate (anode) was ultrasonically cleaned with isopropyl alcohol and pure water (10 minutes each), and then the glass substrate (anode) was exposed to UV light radiation (10 minutes) and ozone for cleaning. Then, the obtained glass substrate (anode) was loaded onto a vacuum deposition device.
[0785] The compound m-MTDTA was vacuum-deposited on a glass substrate (anode) to form a Then, compound HT3 is vacuum-deposited on the hole injection layer to form a hole injection layer having a thickness of A hole transport layer with a thickness of 1000 Å is formed to form a hole transport region.
[0786] Compound 1-35 (as a host) and compound PD11 (as a dopant) were co-deposited on the hole transport region at a weight ratio of 97:3 to form a Thickness of the luminous layer.
[0787] Compound 2-44 is deposited in the light-emitting layer to form a Then, LiF is deposited on the electron transport layer to form a Then, Al is vacuum-deposited on the electron transport region to form a A cathode with a thickness of 100 nm is formed, thereby completing the manufacture of the organic light-emitting device.
[0788] Examples 2-2 to 2-4 and Comparative Examples 2-1 to 2-3
[0789] An organic light-emitting device was manufactured in the same (or substantially the same) manner as Example 2-1, except that in forming the light-emitting layer and the electron transport layer, the compounds listed in Table 2 were used instead of Compounds 1-35 and 2-44, respectively.
[0790] Table 2
[0791]
[0792]
[0793] Example 3-1
[0794] The anode was prepared by cutting a glass substrate, and ITO was deposited on the substrate. The thickness of the glass substrate (anode) was 50 mm x 50 mm x 0.4 mm, and the glass substrate (anode) was ultrasonically cleaned with isopropyl alcohol and pure water (10 minutes each), and then the glass substrate (anode) was exposed to UV light radiation (10 minutes) and ozone for cleaning. Then, the obtained glass substrate (anode) was loaded onto a vacuum deposition device.
[0795] The compound m-MTDTA was vacuum-deposited on a glass substrate (anode) to form a Then, compound HT3 is vacuum-deposited on the hole injection layer to form a hole injection layer having a thickness of A hole transport layer with a thickness of 1000 Å is formed to form a hole transport region.
[0796] Compound 1-1 (as a host) and compound PD13 (as a dopant) were co-deposited on the hole transport region at a weight ratio of 95:5 to form a Thickness of the luminous layer.
[0797] Compound 1-1 is deposited on the light-emitting layer to form a Then, compound 2-38 is deposited on the buffer layer to form a Then, Li is deposited on the electron transport layer to form a Then, Al is vacuum-deposited on the electron transport region to form a A cathode with a thickness of 100 nm is formed, thereby completing the manufacture of the organic light-emitting device.
[0798] Examples 3-2 to 3-5 and Comparative Example 3-1
[0799] An organic light-emitting device was manufactured in the same (or substantially the same) manner as Example 3-1, except that in forming the light-emitting layer, the buffer layer, and the electron transport layer, the compounds listed in Table 3 were used instead of Compounds 1-1 and 2-38, respectively.
[0800] Table 3
[0801]
[0802] Example 4-1
[0803] The anode was prepared by cutting a glass substrate, and ITO was deposited on the substrate. The thickness of the glass substrate (anode) was 50 mm x 50 mm x 0.4 mm, and the glass substrate (anode) was ultrasonically cleaned with isopropyl alcohol and pure water (10 minutes each), and then the glass substrate (anode) was exposed to UV light radiation (10 minutes) and ozone for cleaning. Then, the obtained glass substrate (anode) was loaded onto a vacuum deposition device.
[0804] The compound m-MTDTA was vacuum-deposited on a glass substrate (anode) to form a Then, compound HT3 is vacuum-deposited on the hole injection layer to form a hole injection layer having a thickness of A hole transport layer with a thickness of 1000 Å is formed to form a hole transport region.
[0805] Compound 1-60 (as a host) and compound PD11 (as a dopant) were co-deposited on the hole transport region at a weight ratio of 97:3 to form a Thickness of the luminous layer.
[0806] Compound 1-1 is deposited on the light-emitting layer to form a Then, compound 2-137 is deposited on the buffer layer to form a Then, LiF is deposited on the electron transport layer to form a Then, Al is vacuum-deposited on the electron transport region to form a A cathode with a thickness of 100 nm is formed, thereby completing the manufacture of the organic light-emitting device.
[0807] Example 4-2 and Comparative Example 4-1
[0808] An organic light-emitting device is manufactured in the same (or substantially the same) manner as in Example 4-1, except that in forming the light-emitting layer, the buffer layer, and the electron transport layer, the compounds listed in Table 4 are used instead of Compounds 1-60, 1-1, and 2-137, respectively.
[0809] Table 4
[0810]
[0811] Example 5-1
[0812] The anode was prepared by cutting a glass substrate, and ITO was deposited on the substrate. The thickness of the glass substrate (anode) was 50 mm x 50 mm x 0.4 mm, and the glass substrate (anode) was ultrasonically cleaned with isopropyl alcohol and pure water (10 minutes each), and then the glass substrate (anode) was exposed to UV light radiation (10 minutes) and ozone for cleaning. Then, the obtained glass substrate (anode) was loaded onto a vacuum deposition device.
[0813] The compound m-MTDTA was vacuum-deposited on a glass substrate (anode) to form a Then, compound HT3 is vacuum-deposited on the hole injection layer to form a hole injection layer having a thickness of A hole transport layer with a thickness of 1000 Å is formed to form a hole transport region.
[0814] Compound 1-1 (as a host) and compound PD13 (as a dopant) were co-deposited on the hole transport region at a weight ratio of 95:5 to form a Thickness of the luminous layer.
[0815] Compound 1-1 is deposited on the light-emitting layer to form a Then, compound 2-38 and LiQ are co-deposited on the buffer layer at a weight ratio of 50:50 to form a Then, LiF is deposited on the electron transport layer to form a Then, Al is vacuum-deposited on the electron transport region to form a A cathode with a thickness of 100 nm is formed, thereby completing the manufacture of the organic light-emitting device.
[0816] Example 5-2
[0817] An organic light-emitting device was manufactured in the same (or substantially the same) manner as Example 5-1, except that in forming the light-emitting layer, the buffer layer, and the electron transport layer, the compounds listed in Table 5 were used instead of Compounds 1-1 and 2-38, respectively.
[0818] Table 5
[0819]
[0820] Example 6-1
[0821] The anode was prepared by cutting a glass substrate, and ITO was deposited on the substrate. The thickness of the glass substrate (anode) was 50 mm x 50 mm x 0.4 mm, and the glass substrate (anode) was ultrasonically cleaned with isopropyl alcohol and pure water (10 minutes each), and then the glass substrate (anode) was exposed to UV light radiation (10 minutes) and ozone for cleaning. Then, the obtained glass substrate (anode) was loaded onto a vacuum deposition device.
[0822] The compound m-MTDTA was vacuum-deposited on a glass substrate (anode) to form a Then, compound HT3 is vacuum-deposited on the hole injection layer to form a hole injection layer having a thickness of A hole transport layer with a thickness of 1000 Å is formed to form a hole transport region.
[0823] Compound 1-60 (as a host) and compound PD11 (as a dopant) were co-deposited on the hole transport region at a weight ratio of 97:3 to form a Thickness of the luminous layer.
[0824] Compound 1-1 is deposited on the light-emitting layer to form a Then, compound 2-87 and LiQ are co-deposited on the buffer layer at a weight ratio of 50:50 to form a Then, LiF is deposited on the electron transport layer to form a Then, Al is vacuum-deposited on the electron transport region to form a A cathode with a thickness of 100 nm is formed, thereby completing the manufacture of the organic light-emitting device.
[0825] Example 7-1
[0826] The anode was prepared by cutting a glass substrate, and ITO was deposited on the substrate. The thickness of the glass substrate (anode) was 50 mm x 50 mm x 0.4 mm, and the glass substrate (anode) was ultrasonically cleaned with isopropyl alcohol and pure water (10 minutes each), and then the glass substrate (anode) was exposed to UV light radiation (10 minutes) and ozone for cleaning. Then, the obtained glass substrate (anode) was loaded onto a vacuum deposition device.
[0827] The compound m-MTDTA was vacuum-deposited on a glass substrate (anode) to form a Then, compound HT3 is vacuum-deposited on the hole injection layer to form a hole injection layer having a thickness of A hole transport layer with a thickness of 1000 Å is formed to form a hole transport region.
[0828] Compounds 1-1 and 1-34 (as hosts) and compound PD13 (as dopant) were co-deposited in the hole transport region at a weight ratio of 47.5:47.5:5 to form a Thickness of the luminous layer.
[0829] Compound 2-19 is deposited on the light-emitting layer to form a Then, compound 2-87 and LiQ are co-deposited on the buffer layer in a weight ratio of 50:50 to form a Then, LiF is deposited on the electron transport layer to form a Then, Al is vacuum-deposited on the electron transport region to form a A cathode with a thickness of 100 nm is formed, thereby completing the manufacture of the organic light-emitting device.
[0830] Example 7-2
[0831] An organic light-emitting device is manufactured in the same (or substantially the same) manner as in Example 7-1, except that in forming the light-emitting layer, the buffer layer, and the electron transport layer, the compounds listed in Table 6 are used instead of Compounds 1-1, 1-34, 2-19, and 2-87, respectively.
[0832] Table 6
[0833]
[0834] Evaluation Example
[0835] The driving voltage, current density, efficiency and life of the organic light-emitting devices of Examples 1-1 to 1-4, 2-1 to 2-4, 3-1 to 3-5, 4-1, 4-2, 5-1, 5-2, 6-1, 7-1 and 7-2, and Comparative Examples 1-1 to 1-3, 2-1 to 2-3, 3-1 and 4-1 were evaluated by using a Keithley SMU 236 meter and a PR650 brightness meter. The life results were obtained by measuring the time when the brightness was reduced to 97% of the initial brightness. The results are shown in Table 7.
[0836] Table 7
[0837]
[0838]
[0839]
[0840] Referring to Table 7, it is confirmed that the organic light-emitting devices of Examples 1-1 to 1-4, 2-1 to 2-4, 3-1 to 3-5, 4-1, 4-2, 5-1, 5-2, 6-1, 7-1 and 7-2 each have high efficiency and long life compared with the efficiency and life of the organic light-emitting devices of Comparative Examples 1-1 to 1-3, 2-1 to 2-3, 3-1 and 4-1.
[0841] The organic light-emitting device according to an embodiment of the present disclosure may have low driving voltage, high efficiency, and a long lifespan.
[0842] As used herein, the terms "use," "using," and "used" may be considered synonymous with the terms "utilize," "utilizing," and "utilized," respectively.
[0843] Furthermore, the terms "substantially," "about," and similar terms as used herein 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 are recognized by those of ordinary skill in the art.
[0844] It should be understood that when an element such as a layer, film, region, or substrate is referred to as being "on" another element, it can be directly on the other element or intervening elements may also be present. In contrast, when an element is referred to as being "directly on" or "directly contacting" another element, there are no intervening elements.
[0845] Likewise, any numerical range listed herein is intended to include all sub-ranges of the same numerical precision included in the listed range. For example, the range of "1.0 to 10.0" is intended to include between the listed minimum value 1.0 and the listed maximum value 10.0 (and including the end value), that is, all sub-ranges with a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limit listed herein is intended to include all lower numerical limits included therein and any minimum numerical limit listed in this specification is intended to include all higher numerical limits included therein. Therefore, the applicant reserves the right to modify this specification (including claims) to explicitly list any sub-ranges included in the scope explicitly listed herein.
[0846] It should be understood that the example embodiments described herein should be considered in a descriptive sense rather than 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.
[0847] While one or more embodiments of the present invention 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 following claims and their equivalents.
Claims
1. An organic light-emitting device, comprising: a first electrode; a second electrode; as well as an organic layer between the first electrode and the second electrode, the organic layer comprising a light-emitting layer, wherein the organic layer comprises a first compound represented by Formula 1 and a second compound represented by Formula 2-1, provided that the first compound is not included in the case where it is 4,4'-bis(N-carbazolyl)-1,1'-biphenyl: Formula 1 Formula 2-1 Among them, in formula 1, Ar 11 is a group represented by Formula 1-12 to Formula 1-67, R 11 and R 12 Each is independently selected from the group represented by Formula 8-1, the group represented by Formula 8-2, hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, nitro, substituted or unsubstituted C1-C 60 Alkyl, 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, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) and -P(=O)(Q1)(Q2), L 11 To L 12 Each is independently selected from *-O-*', *-S-*', *-C(=O)-*', *-P(=O)(Q1)-*', *-Si(Q1)(Q2)-*', substituted or unsubstituted C6-C 60 Arylene and substituted or unsubstituted C1-C 60 Heteroarylene, m11 is selected from 1 and 2, a11 and a12 are each independently selected from 0, 1, 2 and 3, n11 and n12 are each independently selected from 0, 1, 2, 3 and 4, In Formulas 1-12 to 1-67 and Formulas 8-1 to 8-2, A 12 and A 13 are each independently selected from phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl and phenanthrolinyl, A 81 and A 82 Each independently selected from C5-C 20 Carbocyclic groups and C1-C 20 Heterocyclic groups, X 11 Selected from N[(L 13 ) a13 -R 13 ]、C[(L 13 ) a13 -R 13 ][(L 14 ) a14 -R 14 ], O and S, X 14 Selected from C(R 101d )(R 101e )、N(R 101d ), O and S, R 13 and R 14 Each is independently selected from the group represented by Formula 8-1, the group represented by Formula 8-2, hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, nitro, substituted or unsubstituted C1-C 60 Alkyl, 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, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) and -P(=O)(Q1)(Q2), wherein when X 11 C[(L 13 ) a13 -R 13 ][(L 14 ) a14 -R 14 ], R 13 and R 14 are optionally connected to each other to form a ring, and when X 14 C(R 101d )(R 101e ), R 101d and R 101e are optionally linked to each other to form a ring, L 13 and L 14 Each is independently selected from *-O-*', *-S-*', *-C(=O)-*', *-P(=O)(Q1)-*', *-Si(Q1)(Q2)-*', substituted or unsubstituted C6-C 60 Arylene and substituted or unsubstituted C1-C 60 Heteroarylene, a13 and a14 are each independently selected from 0, 1, 2 and 3, R 101 , R 102 , R 101a , R 101b , R 101c , R 101d and R 101e are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, nitro, substituted or unsubstituted C1-C 60 Alkyl, 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, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) and -P(=O)(Q1)(Q2), b101, b102, b101a and b101b are each independently selected from 1, 2, 3, 4, 5 and 6, X 81 Selected from N[(L 81 ) a81 -R 81 ]、C[(L 81 ) a81 -R 81 ][(L 82 ) a82 -R 82 ], O and S, X 82 Selected from single bonds, N[(L 83 ) a83 -R 83 ]、C[(L 83 ) a83 -R 83 ][(L 84 ) a84 -R 84 ], O and S, R 85 and R 86 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, nitro, substituted or unsubstituted C1-C 60 Alkyl, 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, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) and -P(=O)(Q1)(Q2), b85 and b86 are each independently selected from 1, 2, 3, 4, 5 and 6, Among them, R 81 To R 84 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, nitro, substituted or unsubstituted C1-C 60 Alkyl, 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, -Si(Q1)(Q2)(Q3), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) and -P(=O)(Q1)(Q2), wherein when X 81 C[(L 81 ) a81 -R 81 ][(L 82 ) a82 -R 82 ], R 81 and R 82 are optionally connected to each other to form a ring, and when X 82 C[(L 83 ) a83 -R 83 ][(L 84 ) a84 -R 84 ], R 83 and R 84 are optionally connected to each other to form a ring, wherein Q1 to Q3 are each 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, L 81 To L 84 Each is independently selected from *-O-*', *-S-*', *-C(=O)-*', *-P(=O)(Q1)-*', *-Si(Q1)(Q2)-*', substituted or unsubstituted C6-C 60 Arylene and substituted or unsubstituted C1-C 60 Heteroarylene, a81 to a84 are each independently selected from 0, 1, 2 and 3, In formula 2-1, X 21 Selected from N and C (R 21 ), X 22 Selected from N and C (R 22 ), X 23 Selected from N and C (R 23 ), X 24 Selected from N and C (R 24 ), X 25 Selected from N and C (R 25 ), selected from X 21 To X 25 At least one of them is N, R 21 To R 25 and R 26a To R 26e Each independently selected from a group represented by any one of Formulas 9-1 to 9-3, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C1-C 60 Alkyl, 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 fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) and -P(=O)(Q1)(Q2), and selected from R 21 To R 25 and R 26a To R 26e At least one of the groups selected from the group represented by Formula 9-1 and the group represented by Formula 9-2, Where R 26c Not including two C1-C 60 Heteroaryl-substituted phenyl, wherein the phenyl and the C1-C 60 There may or may not be a linker between the heteroaryl groups, wherein Q1 to Q3 are each 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, Formula 9-1 Formula 9-2 Formula 9-3 *-(L 91 ) a91 -R 91 *-(L 92 ) a92 -R 92 *-(L 93 ) a93 -R 93 , In formulas 9-1 to 9-3, L 91 Selected from each selected from C1-C 60 Alkyl and C3-C 10 At least one substituted C6-C 60 Arylene and C1-C 60 Heteroarylene, L 92 and L 93 are each independently selected from substituted or unsubstituted C6-C 60 Arylene and substituted or unsubstituted C1-C 60 Heteroarylene, a91 is selected from 1 and 2, a92 and a93 are each independently selected from 0, 1 and 2, R 91 and R 93 are each independently selected from substituted or unsubstituted C6-C 60 Aryl and substituted or unsubstituted C1-C 60 Heteroaryl, R 92 Selected from each selected from C1-C 60 Alkyl and C3-C 10 At least one substituted C6-C 60 Aryl and C1-C 60 heteroaryl, and * and *' each independently indicate a binding site to an adjacent atom.
2. The organic light emitting device according to claim 1, wherein A 12 and A 13 are each independently selected from phenyl and naphthyl, and A 81 and A 82 Each is independently selected from phenyl, naphthyl, phenanthrenyl, anthracenyl, triphenylenyl, pyrenyl, chrysene, furanyl, thienyl, pyrrolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, 2,6-naphthyridinyl, 1,8-naphthyridinyl, 1,5-naphthyridinyl, 1,6-naphthyridinyl, 1,7-naphthyridinyl, 2,7-naphthyridinyl, quinoxalinyl, quinazolinyl, phenanthridinyl, phenanthrolinyl, benzofuranyl, benzothiophenyl, indenyl, indolyl, furopyridyl, thienopyridyl, cyclopentylpyridyl, pyrrolopyridyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, carbazolyl, benzofuranopyrrolyl, benzothiophenylpyrrolyl, indenopyrrolyl, indolopyrrolyl, benzofuranothiphenyl, benzothiophenylthiophenyl, indenothiophenyl, indolothiphenyl, benzofuranofuranyl, benzothiophenylfuranyl, indenofuranyl, indolofuranyl, benzo furopyridyl, benzothienopyridyl, indenopyridyl, indolopyridyl, benzofuranopyrimidinyl, benzothienopyrimidinyl, indenopyrimidinyl, indolopyrimidinyl, benzofuranoindolyl, benzothienoindolyl, indenoindolyl, indolinoindolyl, benzofuranobenzofuranyl, benzothienobenzofuranyl, indenobenzofuranyl, indolobenzofuranyl, benzofuranobenzothienyl, benzothienobenzothienyl , indenobenzothiophenyl, indolebenzothiophenyl, benzofuranoquinolyl, benzothiophenequinolyl, indenoquinolyl, indolequinolyl, benzonaphthofuranyl, benzonaphthothiophenyl, benzofluorenyl, benzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, naphthofuranyl, naphthothiophenyl, cyclopentanaphthyl, spiro-bifluorenyl and spiro-fluorene-indenyl.
3. The organic light emitting device according to claim 1, wherein R 11 To R 14 Each independently selected from the group consisting of: The group represented by formula 8-1, the group represented by formula 8-2, C1-C 20 Alkyl, C6-C 30 Aryl and C1-C 30 heteroaryl; Each of the C6-C 30 Aryl and C1-C 30 Heteroaryl: deuterium, -F, -Cl, -Br, -I, C1-C 20 Alkyl, C1-C 20 Alkoxy, C3-C 10 Cycloalkyl, C6-C 30 Aryl, C1-C 30 Heteroaryl, -N(Q 31 )(Q 32 ) and -Si(Q 31 )(Q 32 )(Q 33 ); Each of the C6-C 30 Aryl and C1-C 30 Heteroaryl: Each is selected from deuterium, -F, -Cl, -Br, -I, Cl-C 20 Alkyl, C1-C 20 Alkoxy, C3-C 10 Cycloalkyl, C6-C 30 Aryl, C1-C 30 Heteroaryl, -N(Q 21 )(Q 22 ) and -Si(Q 21 )(Q 22 )(Q 23 ) at least one substituted C6-C 30 Aryl and C1-C 30 Heteroaryl, Where Q 21 To Q 23 and Q 31 To Q 33 Each independently selected from C1-C 20 Alkyl and C6-C 30 Aryl, R 81 To R 84 Each independently selected from the group consisting of: C1-C 20 Alkyl, C6-C 30 Aryl and C1-C 30 heteroaryl; Each of the C6-C 30 Aryl and C1-C 30 Heteroaryl: deuterium, -F, -Cl, -Br, -I, C1-C 20 Alkyl, C1-C 20 Alkoxy, C3-C 10 Cycloalkyl, C6-C 30 Aryl, C1-C 30 Heteroaryl, -N(Q 31 )(Q 32 ) and -Si(Q 31 )(Q 32 )(Q 33 );as well as Each of the C6-C 30 Aryl and C1-C 30 Heteroaryl: Each is selected from deuterium, -F, -Cl, -Br, -I, Cl-C 20 Alkyl, C1-C 20 Alkoxy, C3-C 10 Cycloalkyl, C6-C 30 Aryl, C1-C 30 Heteroaryl, -N(Q 21 )(Q 22 ) and -Si(Q 21 )(Q 22 )(Q 23 ) at least one substituted C6-C 30 Aryl and C1-C 30 Heteroaryl, Where Q 21 To Q 23 and Q 31 To Q 33 Each independently selected from C1-C 20 Alkyl and C6-C 30 Aryl.
4. The organic light emitting device according to claim 1, wherein The first compound is represented by any one of Group I: <Group I> 5. The organic light emitting device according to claim 1, wherein R 21 To R 25 and R 26a To R 26e Each independently selected from the group consisting of: A group represented by any one of Formulae 9-1 to 9-3, hydrogen, C1-C 20 Alkyl and C3-C 10 Cycloalkyl; C6-C 30 Aryl, C1-C 30 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups; Each of the C6-C 30 Aryl, C1-C 30 Heteroaryl, monovalent non-aromatic fused polycyclic group, and monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, C1-C 20 Alkyl, C3-C 10 Cycloalkyl, C6-C 30 Aryl, C1-C 30 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 31 )(Q 32 ) and -Si(Q 31 )(Q 32 )(Q 33 );as well as Each of the C6-C 30 Aryl, C1-C 30 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups: Each is selected from deuterium, -F, -Cl, -Br, -I, Cl-C 20 Alkyl, C3-C 10 Cycloalkyl, C6-C 30 Aryl, C1-C 30 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 22 ) and -Si(Q 21 )(Q 22 )(Q 23 ) at least one substituted C6-C 30 Aryl, C1-C 30 heteroaryl, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heteropolycyclic group, Where Q 21 To Q 23 and Q 31 To Q 33 Each independently selected from C1-C 20 Alkyl and C6-C 30 Aryl.
6. The organic light emitting device according to claim 1, wherein L 91 Selected from each selected from C1-C 20 at least one substituted phenylene, naphthylene, phenanthrylene, anthracenylene, triphenylene, pyrenylene, chrysene, pyridylene, pyrazylene, pyrimidylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene, phenanthridinylene, acridinylene, phenanthrolinylene and triazinylene, and L 92 and L 93 Each independently selected from the group consisting of: phenylene, naphthylene, phenanthrylene, anthracenylene, triphenylene, pyrenylene, chrysene, pyridylene, pyrazylene, pyrimidylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridylene, quinoxalylene, quinazolinylene, phenanthridylene, acridinylene, phenanthrolinylene and triazinylene; phenylene, naphthylene, phenanthrenylene, anthracenylene, triphenylene, pyrenylene, chrysene, pyridylene, pyrazylene, pyrimidylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridylene, quinoxalylene, quinazolinylene, phenanthridylene, acridinylene, phenanthrolinylene and triazinylene, each of which is substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, tetracenyl, phenanthrenyl, peryl, pentaphenyl, hexacenyl, pentacecenyl, rubenyl, coronenyl, ovalenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isothiazolyl, oxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 );as well as phenylene, naphthylene, phenanthrenylene, anthracenylene, triphenylene, pyrenylene, chrysene, pyridylene, pyrazylene, pyrimidylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridylene, quinoxalylene, quinazolinylene, phenanthridylene, acridinylene, phenanthrolinylene and triazinylene, each of which is substituted by at least one member selected from the group consisting of: Each is selected from deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl, C1-C 20 At least one substituted alkoxy group is a cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, tetracenyl, phenanthrenyl, peryl, pentaphenyl, hexacenyl, pentacecenyl, rubenyl, coronenyl, ovalenyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl , oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl and dibenzocarbazolyl, Where Q 31 To Q 33 Each is independently selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, biphenyl and terphenyl.
7. The organic light emitting device according to claim 1, wherein R 91 and R 93 Each independently selected from the group consisting of: C6-C 30 Aryl and C1-C 30 heteroaryl; Each of the C6-C 30 Aryl and C1-C 30 Heteroaryl: deuterium, -F, -Cl, -Br, -I, C1-C 20 Alkyl, C1-C 20 Alkoxy, C3-C 10 Cycloalkyl, C6-C 30 Aryl, C1-C 30 Heteroaryl, -N(Q 31 )(Q 32 ) and -Si(Q 31 )(Q 32 )(Q 33 );as well as Each of the C6-C 30 Aryl and C1-C 30 Heteroaryl: Each is selected from deuterium, -F, -Cl, -Br, -I, Cl-C 20 Alkyl, C1-C 20 Alkoxy, C3-C 10 Cycloalkyl, C6-C 30 Aryl, C1-C 30 Heteroaryl, -N(Q 21 )(Q 22 ) and -Si(Q 21 )(Q 22 )(Q 23 ) at least one substituted C6-C 30 Aryl and C1-C 30 Heteroaryl, Where Q 21 To Q 23 and Q 31 To Q 33 Each independently selected from C1-C 20 Alkyl and C6-C 30 Aryl, and R 92 Selected from each selected from C1-C 20 phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, triphenylene radical, phenanthrenyl, pyrenyl, tetraphenyl, chrysene radical, pyrrolyl, furanyl, thienyl, pyridyl, pyrazinyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzphenanthrolinyl, thiazolyl, oxazolyl, imidazolyl, triazolyl, indolyl, benzimidazolyl, benzofuranyl, benzothiophenyl and benzoxazolyl radicals.
8. The organic light emitting device according to claim 1, wherein The light-emitting layer comprises a first host and a second host, The first host comprises the first compound, and The first body and the second body are different from each other.
9. The organic light emitting device according to claim 1, wherein The light emitting layer comprises the first compound and a dopant, and The dopant comprises an organic metal complex represented by Formula 401: Formula 401 M(L 401 ) xc1 (L 402 ) xc2 Formula 402 in, In formula 401, M is selected from iridium, platinum, palladium, osmium, titanium, zirconium, hafnium, europium, terbium, rhodium and thulium, L 401 is selected from the ligand represented by formula 402, and xc1 is 1, 2 or 3, wherein when xc1 is 2 or greater, two or more L 401 Same or different from each other, L 402 is an organic ligand, and xc2 is an integer selected from 0 to 4, wherein when xc2 is 2 or greater, two or more L 402 Same or different from each other, Wherein, in Formula 402, X 401 To X 404 are each independently nitrogen or carbon, X 401 and X 403 are connected to each other via a single bond or a double bond, and X 402 and X 404 connected to each other via single or double bonds, A 401 and A 402 Each independently is C5-C 60 Carbocyclic group or C1-C 60 Heterocyclic groups, X 405 selected from a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 411 )-*'、*-C(Q 411 )(Q 412 )-*', *-C(Q 411 )=C(Q 412 )-*’, *-C(Q 411 )=*’ and *=C(Q 411 )=*’, where Q 411 and Q 412 are each independently selected from hydrogen, deuterium, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl and naphthyl, X 406 is selected from a single bond, O and S, R 401 and R 402 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, -CD3, -CF3, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C1-C 20 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 fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O)2(Q 401 ) and -P(=O)(Q 401 )(Q 402 ), where Q 401 To Q 403 Each independently selected from C1-C 10 Alkyl, C1-C 10 Alkoxy, C6-C 20 Aryl and C1-C 20 Heteroaryl, xc11 and xc12 are each independently an integer selected from 0 to 10, and * and *' in Formula 402 each independently indicate a binding site with M in Formula 401.
10. The organic light emitting device according to claim 1, wherein The organic layer includes an electron transport region between the light emitting layer and the second electrode, The electron transport region comprises an electron transport layer and an electron injection layer, and The electron transport layer includes at least one selected from an alkali metal complex and an alkaline earth metal complex.
11. The organic light emitting device according to claim 1, wherein The organic layer includes an electron transport region between the light emitting layer and the second electrode, The electron transport region comprises an electron transport layer and an electron injection layer, and The electron injection layer comprises an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex or a combination thereof.
12. The organic light emitting device according to claim 1, wherein The organic layer includes a hole transport region between the light emitting layer and the first electrode, The hole transport region comprises a p-type dopant, and The p-type dopant has a lowest unoccupied molecular orbital energy level of -3.5 eV or less.
13. The organic light emitting device according to claim 12, wherein The p-type dopant includes a cyano-containing compound.
14. The organic light emitting device according to claim 1, wherein The light-emitting layer is a first color light-emitting layer, The organic layer further comprises i) at least one second color light emitting layer, wherein the first color light and the second color light are the same or different from each other, or ii) at least one second color light emitting layer and at least one third color light emitting layer, wherein the first color light, the second color light and the third color light are the same or different from each other, and When the organic light emitting device is in operation, it emits mixed light including the first color light and the second color light, or emits mixed light including the first color light, the second color light, and the third color light.
Citation Information
Patent Citations
Compound for organic electroluminescent device and organic electroluminescent device
CN101511834A
Composition and organic optoelectric device and display device
CN104277824A
Organic electroluminescent element
JP2013201153A
Hetero-cyclic compound and organic light emitting device comprising the same
KR1020150140241A
Material for organic electroluminescence device and organic electroluminescence device
US20130234119A1