Light-emitting device, electronic apparatus, electronic device, and heterocyclic compound
By using heterocyclic compounds with high triplet energy level and high deuterium substitution rate in the emission layer of the light emitting device, the shortcomings of the existing light emitting devices in terms of color purity and luminous efficiency are solved, and better driving voltage, maximum quantum efficiency, service life and color purity are achieved.
Patent Information
- Application Number
- CN202411401227.7
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2023-10-18
- Filing Date
- 2024-10-09
- Publication Date
- 2025-04-18
AI Technical Summary
The existing light emitting devices have shortcomings in color purity and luminous efficiency, especially in terms of service life and driving voltage.
Using an emission layer containing a heterocyclic compound, the color purity and luminescence efficiency of the luminescent device are improved and the service life is extended through the high triplet energy level and high deuterium substitution rate of the heterocyclic compound.
The excellent driving voltage, maximum quantum efficiency, service life and color purity of the light emitting device are achieved, and the luminous performance is significantly improved.
Smart Images

Figure CN119841856A_ABST
Abstract
Description
[0001] CROSS-REFERENCE TO RELATED APPLICATIONS
[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0139857 filed in the Korean Intellectual Property Office on October 18, 2023, the entire contents of which are incorporated herein by reference. Technical Field
[0003] The embodiment relates to a light-emitting device including a heterocyclic compound, an electronic device including the light-emitting device, an electronic device including the light-emitting device, and the heterocyclic compound. Background Art
[0004] Among light-emitting devices, an organic light-emitting device is a self-emitting device having a wide viewing angle, a high contrast ratio, a short response time, and excellent characteristics in terms of brightness, driving voltage, and response speed compared to devices in the art.
[0005] As an example, an organic light-emitting device may have a structure in which a first electrode is arranged on a substrate and a hole transport region, an emission layer, an electron transport region, and a second electrode are sequentially formed on the first electrode. Holes provided by the first electrode move toward the emission layer through the hole transport region, and electrons provided by the second electrode move toward the emission layer through the electron transport region. Carriers such as holes and electrons recombine in the emission layer to generate excitons. The excitons transition from an excited state to a ground state, thereby generating light.
[0006] It should be understood that this background technology section is intended, in part, to provide a useful background for understanding the technology. However, this background technology section may also include concepts, ideas or cognitions that were not known or understood by a person skilled in the relevant art before the corresponding effective filing date of the subject matter disclosed herein. Summary of the invention
[0007] Embodiments include a light-emitting device including a heterocyclic compound, an electronic device including the light-emitting device, an electronic device including the light-emitting device, and the heterocyclic compound.
[0008] 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 embodiments of the disclosure.
[0009] The embodiment provides a light emitting device, which may include
[0010] The first electrode,
[0011] a second electrode facing the first electrode,
[0012] an intermediate layer between the first electrode and the second electrode and including an emission layer, and
[0013] A heterocyclic compound represented by Formula 1.
[0014] [Formula 1]
[0015]
[0016] [Formula 2]
[0017]
[0018] In equation 1 and equation 2,
[0019] X 1 It can be C, Si, Ge or Sn,
[0020] R 11 , R 12 , R 13 , R 2 , R 3 , R 41 To R 45 and R 51 To R 53 Each of them may be independently a group represented by Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy groups, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Arylthio group, -Si(Q 1 )(Q 2 )(Q3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) or -P(=O)(Q 1 )(Q 2 ),
[0021] But R 41 , R 42 , R 44 and R 45 At least one of may be each independently a group represented by Formula 2, and
[0022] R 43 may not be a group represented by Formula 2,
[0023] n2 can be an integer from 0 to 4,
[0024] n3 can be an integer from 0 to 7,
[0025] n51 can be an integer from 0 to 5,
[0026] n52 and n53 may each independently be an integer from 0 to 20,
[0027] Cyclo 1 and CY 2 Can be C independently 5 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic groups,
[0028] * indicates the binding site with the adjacent atom,
[0029] R 10a It can be:
[0030] deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group or a nitro group;
[0031] Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 7-C 60 Arylalkyl group, C 2 -C 60 Heteroarylalkyl groups, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof substituted C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group or C 1 -C 60 Alkoxy groups;
[0032] Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 7 -C 60 Arylalkyl group, C 2 -C 60 Heteroarylalkyl groups, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof substituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 7 -C 60 Arylalkyl group or C 2 -C 60 a heteroarylalkyl group; or
[0033] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ),as well as
[0034] Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can each independently be: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; C 1 -C 60 Alkyl group; C 2 -C 60 Alkenyl group; C 2 -C 60 Alkynyl group; C 1 -C 60 alkoxy groups; or each unsubstituted or substituted with deuterium, -F, cyano groups, C 1 -C 60 Alkyl group, C 1 -C 60 C substituted with an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group or any combination thereof 3 -C 60 Carbocyclic group, C1 -C 60 Heterocyclic group, C 7 -C 60 Arylalkyl group, or C 2 -C 60 Heteroarylalkyl groups.
[0035] In an embodiment, the emission layer may include the heterocyclic compound.
[0036] In an embodiment, the emission layer may include a host, and the host may include the heterocyclic compound.
[0037] In an embodiment, the emissive layer may further include an emitter, a sensitizer, or any combination thereof.
[0038] In an embodiment, the emission layer may further include a phosphorescent compound, a fluorescent compound, or any combination thereof.
[0039] In an embodiment, the emitting layer may emit blue light.
[0040] According to the embodiment, an electronic device may include the light emitting device.
[0041] In an embodiment, the electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarization layer, or any combination thereof.
[0042] According to the embodiment, the electronic device may include the light emitting device.
[0043] In an embodiment, the electronic device can be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a retractable display, a laser printer, a phone, a mobile phone, a tablet personal computer, a tablet phone, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall with multiple displays stitched together, a theater screen, a stadium screen, a light therapy device, or a sign.
[0044] Embodiments provide heterocyclic compounds which may be represented by Formula 1 explained herein.
[0045] In an embodiment, CY 1 and CY 2 Each may independently be a benzene group, a naphthyl group or a phenanthrene group.
[0046] In an embodiment, R11 , R 12 , R 13 , R 2 , R 3 , R 41 To R 45 and R 51 To R 53 Can be independently:
[0047] A group represented by Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, C 1 -C 20 Alkyl group or C 1 -C 20 Alkoxy groups;
[0048] Each was deuterated, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C 1 -C 10 C substituted with an alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridyl group or a pyrimidinyl group. 1 -C 20 Alkyl group or C 1 -C 20 Alkoxy groups;
[0049] Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20an alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a 1,2,3,4-tetrahydronaphthyl group, a phenyl group, a biphenyl group, a terphenyl group, (C 1 -C 10 alkyl)phenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a pyrrolyl group, a thienyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group group, a carbazolyl group, a phenanthroline group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzisothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazine group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidinyl group, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ) substituted cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, 1,2,3,4-tetrahydronaphthyl group, phenyl group, biphenyl group, terphenyl group, (C 1 -C 10 alkyl)phenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a pyrrolyl group, a thienyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group , a benzofuranyl group, a benzothienyl group, a benzisothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothienyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothienyl group, an azafluorenyl group, or an azadibenzosilyl group; or
[0050] -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 ) or -P(=O)(Q 1 )(Q 2 ),
[0051] But R 41 , R 42 , R 44 and R 45 At least one of may be each independently a group represented by Formula 2, and
[0052] R 43 may not be a group represented by Formula 2, and
[0053] Q 1 To Q 3 and Q 31 To Q 33 Can be independently:
[0054] -CH 3 、-CD 3 、-CD 2 H.-CDH 2 、-CH 2 CH 3 、-CH 2 CD3 、-CH 2 CD 2 H, -CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H, -CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 H or -CD 2 CDH 2 ;or
[0055] Each is unsubstituted or replaced by deuterium, C 1 -C 10 An n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group, naphthyl group, pyridyl group, pyrimidinyl group, pyridazinyl group, pyrazinyl group or triazinyl group substituted with an alkyl group, a phenyl group, a biphenyl group, a tert-biphenyl group, a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group or a triazinyl group.
[0056] In an embodiment, R 51 It may be a group represented by one of Formula 5-1 to Formula 5-19 explained below.
[0057] In the embodiment, the group represented by Formula 2 may be represented by one of Formulae 2-1 to 2-8 explained below.
[0058] In an embodiment, the heterocyclic compound may be represented by one of Formula 1-1 to Formula 1-4 explained below.
[0059] In embodiments, the heterocyclic compound may contain at least one deuterium.
[0060] In embodiments, the heterocyclic compound may have a deuterium substitution rate greater than or equal to about 9.5%.
[0061] In embodiments, the heterocyclic compound may have a triplet energy level of about 2.75 eV to about 3.10 eV.
[0062] In the embodiment, the heterocyclic compound may be one of Compound 1 to Compound 40 explained below.
[0063] It should be understood that the above embodiments have been described in a generic and explanatory sense only and not for purposes of limitation, and that the present disclosure is not limited to the above-described embodiments. BRIEF DESCRIPTION OF THE DRAWINGS
[0064] The accompanying drawings are included to provide a further understanding of the embodiments, and are incorporated into and constitute a part of this specification. The accompanying drawings illustrate embodiments of the present disclosure and principles thereof. The above and other aspects and features of the present disclosure will become more apparent by describing the embodiments of the present disclosure in detail with reference to the accompanying drawings, in which:
[0065] Figure 1 is a schematic cross-sectional view of the structure of a light emitting device according to the embodiment;
[0066] Figure 2 is a schematic cross-sectional view of a structure of an electronic device according to an embodiment;
[0067] Figure 3 is a schematic cross-sectional view of a structure of an electronic device according to another embodiment;
[0068] Figure 4 is a schematic perspective view of an electronic device including a light emitting device according to the embodiment;
[0069] Figure 5 is a schematic perspective view of the exterior of a vehicle as an electronic device including a light emitting device according to the embodiment; and
[0070] FIG. 6A to FIG. 6C Each is a schematic perspective view of the interior of a vehicle according to various embodiments. DETAILED DESCRIPTION
[0071] The present disclosure will now be described more fully below with reference to the accompanying drawings in which embodiments are shown. However, the present disclosure may be implemented in different forms and should not be construed as being limited to the embodiments set forth herein. Instead, these embodiments are provided so that the present disclosure will be thorough and complete, and will fully convey the scope of the present disclosure to those skilled in the art.
[0072] In the drawings, the size, thickness, ratio, and dimensions of elements may be exaggerated for ease of description and for clarity. The same reference numerals and / or the same reference characters refer to the same elements throughout.
[0073] In the description, it should be understood that when an element (or region, layer, component, etc.) is referred to as being "on," "connected to," or "coupled to" another element, it may be directly on, directly connected to, or directly coupled to the other element, or one or more intervening elements may exist therebetween. In a similar sense, when an element (or region, layer, component, etc.) is described as "covering" another element, it may directly cover the other element, or one or more intervening elements may exist therebetween.
[0074] In the description, when an element is "directly on," "directly connected to," or "directly coupled to" another element, there are no intervening elements. For example, "directly on" may mean that two layers or two elements are disposed without additional elements, such as adhesive elements, in between.
[0075] As used herein, expressions used in the singular such as “a”, “an” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise.
[0076] As used herein, the term "and / or" includes any and all combinations of one or more than one of the associated listed items. For example, "A and / or B" may be understood to mean "A, B, or A and B". The terms "and" and "or" may be used in the sense of conjunctions or antithesis conjunctions and may be understood to be equivalent to "and / or".
[0077] In the specification and claims, for the purpose of its meaning and interpretation, the term "at least one of..." is intended to include the meaning of "at least one selected from the group consisting of..." For example, "at least one of A, B, and C" can be understood to mean only A, only B, only C, or any combination of two or more than two of A, B, and C, such as ABC, ACC, BC, or CC. When preceding a list of elements, the term "at least one of..." modifies the entire list of elements and does not modify the individual elements of the list.
[0078] It should be understood that although the terms first, second, etc. can be used to describe various elements in this article, these elements should not be limited by these terms. These terms are only used to distinguish one element from another element. Therefore, without departing from the teaching of the present disclosure, the first element can be referred to as the second element. Similarly, without departing from the scope of the present disclosure, the second element can be referred to as the first element.
[0079] For ease of description, spatially relative terms "below," "under," "down," "above," "upper," etc. may be used herein to describe the relationship between one element or component and another element or component as illustrated in the drawings. It should be understood that spatially relative terms are intended to cover different orientations of the device when in use or operation in addition to the orientation depicted in the drawings. For example, in a case where the device illustrated in the drawings is flipped, a device located "below" or "below" another device may be placed "above" the other device. Therefore, the exemplary term "below" may include both a lower position and an upper position. The device may also be oriented in other directions, and therefore spatially relative terms may be interpreted differently depending on the orientation.
[0080] As used herein, the term "about" or "approximately" includes the stated value and means within an acceptable range of deviation of the stated value as determined by one of ordinary skill in the art taking into account the relevant measurements and the errors associated with the measurement of the quantity (i.e., the limits of the measurement system). For example, "about" can mean within one or more than one standard deviation, or within ±20%, ±10%, or ±5% of the stated value.
[0081] It should be understood that the terms “comprises,” “comprising,” “includes,” “including,” “have,” “having,” “contains,” “containing” and the like are intended to specify the presence of specified features, integers, steps, operations, elements, components or combinations thereof in the present disclosure, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components or combinations thereof.
[0082] Unless otherwise defined or implied herein, all terms (including technical and scientific terms) used have the same meaning as commonly understood by those skilled in the art to which the present disclosure belongs. It should be further understood that terms (such as those defined in commonly used dictionaries) should be interpreted as having a meaning consistent with their meaning in the context of the relevant art, and should not be interpreted in an idealized or overly formal sense unless clearly defined in the specification.
[0083] The light emitting device (eg, organic light emitting device) according to the embodiment may include: a first electrode; a second electrode facing the first electrode; an intermediate layer between the first electrode and the second electrode and including an emission layer, and a heterocyclic compound represented by Formula 1.
[0084] Hereinafter, a description of the heterocyclic compound represented by Formula 1 is provided.
[0085] [Formula 1]
[0086]
[0087] [Formula 2]
[0088]
[0089] In equation 1 and equation 2,
[0090] X 1 It can be C, Si, Ge or Sn.
[0091] In an embodiment, X 1 It can be Si or Ge.
[0092] In an embodiment, X 1 It may be Si. * indicates the bonding site with the adjacent atom.
[0093] In equation 1 and equation 2,
[0094] R 11 , R 12 , R 13 , R 2 , R 3 , R 41 To R 45 and R 51 To R 53 Each of them may be independently a group represented by Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 6 -C 60 Aryloxy groups, unsubstituted or substituted with at least one R 10a Substituted C6 -C 60 Arylthio 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 ) or -P(=O)(Q 1 )(Q 2 ). 10a Can be the same as described herein.
[0095] In an embodiment, R 11 , R 12 , R 13 , R 2 , R 3 , R 41 To R 45 and R 51 To R 53 Can be independently:
[0096] A group represented by Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, C 1 -C 20 Alkyl group or C 1 -C 20 Alkoxy groups;
[0097] Each was deuterated, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C 1 -C 10 C substituted with an alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridyl group or a pyrimidinyl group. 1 -C 20 Alkyl group or C 1 -C 20 Alkoxy groups;
[0098] Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a 1,2,3,4-tetrahydronaphthyl group, a phenyl group, a biphenyl group, a terphenyl group, (C 1 -C 10 alkyl)phenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a pyrrolyl group, a thienyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group group, a carbazolyl group, a phenanthroline group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzisothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazine group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidinyl group, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32) substituted cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, 1,2,3,4-tetrahydronaphthyl group, phenyl group, biphenyl group, terphenyl group, (C 1 -C 10 alkyl)phenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a pyrrolyl group, a thienyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group , a benzofuranyl group, a benzothienyl group, a benzisothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothienyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothienyl group, an azafluorenyl group, or an azadibenzosilyl group; or
[0099] -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 ) or -P(=O)(Q 1 )(Q 2 ),as well as
[0100] Q 1 To Q 3 and Q 31 To Q 33 Can be independently:
[0101] -CH 3 、-CD 3 、-CD 2 H.-CDH 2 、-CH 2 CH3 、-CH 2 CD 3 、-CH 2 CD 2 H, -CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H, -CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 H or -CD 2 CDH 2 ;or
[0102] Each is unsubstituted or replaced by deuterium, C 1 -C 10 An n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group, naphthyl group, pyridyl group, pyrimidinyl group, pyridazinyl group, pyrazinyl group or triazinyl group substituted with an alkyl group, a phenyl group, a biphenyl group, a tert-biphenyl group, a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group or a triazinyl group.
[0103] In an embodiment, R 11 , R 12 and R 13 Can be independently:
[0104] hydrogen, deuterium, -F or a cyano group;
[0105] unsubstituted or deuterated, -F, cyano group, phenyl group, deuterated phenyl group, fluorophenyl group, (C 1 -C 20 alkyl)phenyl group, biphenyl group, terphenyl group, deuterated biphenyl group, deuterated terphenyl group, fluorinated biphenyl group, fluorinated terphenyl group, (C 1 -C 20 Alkyl)biphenyl group, (C 1 -C 20 C 1 -C 20 Alkyl groups;
[0106] Each is unsubstituted or substituted with deuterium, -F, cyano group, C 1 -C 20 Alkyl groups, deuterated C 1 -C20 Alkyl groups, fluorinated C 1 -C 20 Alkyl group, C 3 -C 10 Cycloalkyl groups, deuterated C 3 -C 10 Cycloalkyl groups, fluorinated C 3 -C 10 Cycloalkyl group, phenyl group, deuterated phenyl group, fluorophenyl group, (C 1 -C 20 alkyl)phenyl group, biphenyl group, deuterated biphenyl group, fluorinated biphenyl group, (C 1 -C 20 alkyl) biphenyl group, terphenyl group, deuterated terphenyl group, fluorinated terphenyl group, (C 1 -C 20 Alkyl) terphenyl or any combination thereof substituted C 3 -C 10 a cycloalkyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a carbazolyl group, a dibenzofuranyl group or a dibenzothiophenyl group.
[0107] In an embodiment, R 51 It may be a group represented by one of Formula 5-1 to Formula 5-19:
[0108]
[0109]
[0110]
[0111] In Formula 5-1 to Formula 5-19, z3 may be an integer from 0 to 3, z4 may be an integer from 0 to 4, z5 may be an integer from 0 to 5, z7 may be an integer from 0 to 7, and R 10a Can be the same as described herein.
[0112] In equation 1 and equation 2,
[0113] R 41 , R 42 , R 44 and R 45 At least one of them may be independently a group represented by Formula 2, and R 43 The group other than that represented by Formula 2 may be used.
[0114] In an implementation scheme,
[0115] R 41 It may be a group represented by Formula 2,
[0116] R 42 It may be a group represented by Formula 2,
[0117] R 44 It may be a group represented by Formula 2,
[0118] R 45 It may be a group represented by Formula 2, or
[0119] R 41 , R 42 , R 44 and R 45 Any combination of may each independently be a group represented by Formula 2.
[0120] In an embodiment, R 43 may not be a group represented by Formula 2 and may not contain a group represented by Formula 2. For example, R 43 The carbazole group may not be contained.
[0121] In equation 1 and equation 2,
[0122] n2 can be an integer from 0 to 4,
[0123] n3 can be an integer from 0 to 7,
[0124] n51 can be an integer from 0 to 5, and
[0125] n52 and n53 may each independently be an integer of 0 to 20.
[0126] In equation 1 and equation 2,
[0127] Cyclo 1 and CY 2 Can be C independently 5 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic group.
[0128] In an embodiment, CY 1 and CY 2 Each may independently be a benzene group, a naphthyl group or a phenanthrene group.
[0129] In an embodiment, CY 1 and CY 2 They may each independently be a phenyl group.
[0130] In equation 1 and equation 2,
[0131] * can indicate the binding site with the adjacent atom.
[0132] In an embodiment, * may represent R41 , R 42 , R 44 and R 45 A binding site between one of the formulas 2 and .
[0133] In equation 1 and equation 2,
[0134] R 10a It can be:
[0135] deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group or a nitro group;
[0136] Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 7 -C 60 Arylalkyl group, C 2 -C 60 Heteroarylalkyl groups, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof substituted C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group or C 1 -C 60 Alkoxy groups;
[0137] Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C60 Alkynyl group, C 1 -C 60 Alkoxy groups, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 7 -C 60 Arylalkyl group, C 2 -C 60 Heteroarylalkyl groups, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof substituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 7 -C 60 Arylalkyl group, or C 2 -C 60 a heteroarylalkyl group; or
[0138] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ),as well as
[0139] Q 11 To Q13 , Q 21 To Q 23 and Q 31 To Q 33 can each independently be: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; C 1 -C 60 Alkyl group; C 2 -C 60 Alkenyl group; C 2 -C 60 Alkynyl group; C 1 -C 60 alkoxy groups; or each unsubstituted or substituted with deuterium, -F, cyano groups, C 1 -C 60 Alkyl group, C 1 -C 60 C substituted with an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group or any combination thereof 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 7 -C 60 Arylalkyl group, or C 2 -C 60 Heteroarylalkyl groups.
[0140] In an embodiment, the group represented by Formula 2 may be a group represented by one of Formulas 2-1 to 2-8:
[0141]
[0142] In Formula 2-1 to Formula 2-8,
[0143] R 51 and n51 may each be the same as described in Formula 2,
[0144] R 52a , R 52b , R 52c , R 52d , R 52e and R 52f can be independently related to R in Formula 2 52 Same description,
[0145] R 53a , R 53b , R 53c and R 53d can be independently related to R in Formula 2 53 Same as described, and
[0146] * can indicate the binding site with the adjacent atom.
[0147] In an embodiment, the heterocyclic compound may be a heterocyclic compound represented by one of Formula 1-1 to Formula 1-4:
[0148] [Formula 1-1]
[0149]
[0150] [Formula 1-2]
[0151]
[0152] [Formula 1-3]
[0153]
[0154] [Formula 1-4]
[0155]
[0156] In Formula 1-1 to Formula 1-4,
[0157] X 1 , R 11 To R 13 and R 41 To R 45 may each be the same as described in Formula 1,
[0158] R 21 To R 24 can be independently related to R in Formula 1 2 Same as described, and
[0159] R 31 To R 38 can be independently related to R in Formula 1 3 Same as described.
[0160] In embodiments, the heterocyclic compound may contain at least one deuterium.
[0161] In an embodiment, the heterocyclic compound may have a deuterium substitution rate greater than or equal to about 9.5%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 100%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 10% to about 100%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 15% to about 100%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 20% to about 100%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 25% to about 100%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 30% to about 100%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 35% to about 100%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 40% to about 100%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 45% to about 100%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 50% to about 100%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 55% to about 100%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 60% to about 100%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 65% to about 100%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 70% to about 100%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 75% to about 100%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 80% to about 100%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 85% to about 100%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 90% to about 100%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 95% to about 100%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 97.5%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 95%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 92.5%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 90%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 87.5%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 85%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 82.5%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 80%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 77.5%.For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 75%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 72.5%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 70%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 67.5%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 65%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 62.5%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 60%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 57.5%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 55%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 52.5%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 50%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 47.5%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 45%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 42.5%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 40%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 37.5%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 35%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 32.5%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 30%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 27.5%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 25%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 22.5%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 20%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 17.5%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 15%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 12.5%. For example, the heterocyclic compound represented by Formula 1 may have a deuterium substitution rate of about 9.5% to about 10%.
[0162] In an embodiment, the term "deuterium substitution rate" can be interpreted as 9.5% or more of hydrogens at the substitutable positions in the corresponding structure are substituted by deuterium. For example, in the case where the corresponding structure is dibenzofuran, when the deuterium substitution rate of dibenzofuran is 25%, it can mean that two of the eight hydrogens at the substitutable positions of dibenzofuran are substituted by deuterium.
[0163] The "deuterium substitution rate" can be measured by nuclear magnetic resonance spectroscopy ( 1 H-NMR), thin layer chromatography / mass spectrometry (TLC / MS), or gas chromatography / mass spectrometry (GC / MS).
[0164] In an embodiment, the heterocyclic compound may include two carbazole groups.
[0165] In an embodiment, the heterocyclic compound may include a silicon (Si).
[0166] In an embodiment, the heterocyclic compound can be one of Compound 1 to Compound 40:
[0167]
[0168]
[0169]
[0170] In embodiments, the heterocyclic compound may have a triplet energy level of about 2.75 eV to about 3.10 eV.
[0171] The heterocyclic compound represented by Formula 1 according to the embodiment may include a core including a carbazole group and a substituent including a nitrogen-containing ring, and may further include a benzene linker connecting the nitrogen-containing ring to the core including the carbazole group.
[0172] The nitrogen-containing ring can be substituted into the carbazole group at the ortho or meta position relative to the benzene linker, thereby improving the steric effect and thus having a triplet energy level, and thus, when the heterocyclic compound is used in the emission layer, the color purity and luminous efficiency can be greatly improved.
[0173] In an embodiment, the heterocyclic compound may include a substituent containing a Group 14 element substituted into the N of the carbazole group to control the interaction with the phosphorescent dopant, and has a high triplet energy level, and therefore, when the heterocyclic compound is used in the emission layer, the color purity and luminous efficiency can be greatly improved.
[0174] In an embodiment, in a heterocyclic compound, the benzene linker may be substituted at the carbon atoms at the 1- to 4-positions in the carbazole core group, and the nitrogen-containing ring may be substituted via the ring CY of the nitrogen-containing ring. 1Attachment to a benzene linker further improves steric effects and ensures a high triplet energy level.
[0175] Because the heterocyclic compound can contain at least one deuterium, it has the advantage of improving the service life, and because the deuterium substitution rate increases, the service life of the light-emitting device can be improved. Due to the high triplet energy level, long service life and improved characteristics in the y color coordinate, when the heterocyclic compound is used for the emission layer, the service life, color purity and luminous efficiency can be greatly improved.
[0176] Therefore, a light-emitting device including the heterocyclic compound may have excellent driving voltage, excellent maximum quantum efficiency characteristics, excellent lifespan characteristics, and excellent color purity characteristics.
[0177] A person of ordinary skill in the art may recognize a method for synthesizing the heterocyclic compound represented by Formula 1 by referring to the Synthesis Examples and / or Examples provided below.
[0178] At least one heterocyclic compound represented by Formula 1 may be used in a light-emitting device (e.g., an organic light-emitting device). Therefore, the embodiment provides a light-emitting device, which may include: a first electrode; a second electrode facing the first electrode; an intermediate layer between the first electrode and the second electrode and including an emission layer; and a heterocyclic compound represented by Formula 1.
[0179] In an implementation scheme,
[0180] The first electrode of the light emitting device may be an anode,
[0181] The second electrode of the light emitting device may be a cathode,
[0182] The intermediate layer may further include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode,
[0183] The hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof, and
[0184] The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0185] The hole transport layer may include a single layer or two or more layers, and the electron transport layer may include a single layer or two or more layers.
[0186] In the embodiment, the heterocyclic compound may be included between the first electrode and the second electrode of the light emitting device. Therefore, the heterocyclic compound may be included in the intermediate layer of the light emitting device, for example, in the emission layer of the intermediate layer.
[0187] In an embodiment, the emission layer in the intermediate layer of the light-emitting device may include a dopant and a host, and the host may include a heterocyclic compound. For example, a heterocyclic compound may be used as a host. The emission layer may emit red light, green light, blue light and / or white light. In an embodiment, the emission layer may emit blue light. The blue light may have a maximum emission wavelength of, for example, about 400nm to about 490nm. The blue light may emit light with a maximum emission wavelength of, for example, about 430nm to about 480nm.
[0188] In an embodiment, the emission layer in the intermediate layer of the light-emitting device may include a dopant and a host, the host may include a heterocyclic compound, and the dopant may emit blue light. For example, the dopant may include a transition metal and a number m of ligands, and m may be an integer from 1 to 6. The number m of ligands may be the same as or different from each other, at least one of the number m of ligands may be bonded to the transition metal via a carbon-transition metal bond, and the carbon-transition metal bond may be a coordination bond. For example, at least one of the number m of ligands may be a carbene ligand (e.g., Ir(pmp) 3 The transition metal may be, for example, iridium, platinum, osmium, palladium, rhodium, gold, etc. The emissive layer and dopant may be the same as described herein.
[0189]
[0190] In an embodiment, the emission layer of the light emitting device may further include an emitter, a sensitizer, or any combination thereof.
[0191] In the embodiment, the emission layer of the light emitting device may further include a phosphorescent compound, a fluorescent compound, or any combination thereof. For example, the phosphorescent compound may be a compound represented by Formula 401 as described herein. For example, the fluorescent compound may be a compound represented by Formula 501 as described herein.
[0192] In an embodiment, the fluorescent compound of the light emitting device may include an instantaneous fluorescent compound, a thermally activated delayed fluorescent (TADF) compound, or a combination thereof. For example, the TADF compound may be a delayed fluorescent material as described herein.
[0193] In an embodiment, the emission layer of the light emitting device may further include an organic metal compound containing a transition metal, a compound containing boron (B), or any combination thereof.
[0194] For example, the heterocyclic compound represented by Formula 1 may be an emitter or a sensitizer, depending on the types of other materials included in the emission layer.
[0195] For example, the transition metal-containing organometallic compound and the boron (B)-containing compound can each independently be an emitter or a sensitizer, depending on the type of other materials included in the emissive layer.
[0196] For example, the emission layer can emit phosphorescence or fluorescence, each of which is emitted from an organic metal compound containing a transition metal or a compound containing boron (B), and the organic metal compound containing a transition metal and the compound containing boron (B) can each independently be a phosphorescent compound or a fluorescent compound, wherein, when the organic metal compound containing a transition metal and the compound containing boron (B) are each fluorescent compounds, the organic metal compound containing a transition metal and the compound containing boron (B) can each be an instantaneous fluorescent compound or a TADF compound.
[0197] For example, the organic metal compound containing a transition metal may be a phosphorescent compound, and the compound containing boron (B) may be a delayed fluorescence compound.
[0198] In an embodiment, the transition metal-containing organometallic compound may include platinum and a tetradentate ligand bonded to the platinum. For example, one of the bonds between the tetradentate ligands may be a platinum-carbene bond. For example, the transition metal-containing organometallic compound may be an organometallic compound represented by Formula 401 as described herein.
[0199] In an embodiment, the boron (B)-containing compound may be a C-containing compound comprising at least two fused cyclic groups sharing boron (B). 8 -C 60 Compounds containing polycyclic groups. For example, the boron (B)-containing compound may contain at least one cyclic group containing each of boron and nitrogen as ring-forming atoms.
[0200] In an embodiment, the light emitting device may include a covering layer outside the first electrode or outside the second electrode.
[0201] In the embodiment, the light emitting device may further include at least one of a first covering layer outside the first electrode and a second covering layer outside the second electrode, and at least one of the first covering layer and the second covering layer may include a heterocyclic compound represented by Formula 1. The first covering layer and / or the second covering layer may each be as described herein.
[0202] In an embodiment, the light emitting device may further include:
[0203] A first covering layer outside the first electrode and including a heterocyclic compound represented by Formula 1;
[0204] a second covering layer outside the second electrode and including the heterocyclic compound represented by Formula 1; or
[0205] A first covering layer and a second covering layer.
[0206] The expression “(the intermediate layer and / or the covering layer) contains at least one heterocyclic compound” as used herein may mean “(the intermediate layer and / or the covering layer) may contain one kind of heterocyclic compound represented by Formula 1 or two different kinds of heterocyclic compounds each represented by Formula 1”.
[0207] In the embodiment, the intermediate layer and / or the covering layer may contain only compound 1 as a heterocyclic compound. For example, compound 1 may be present in the emission layer of the light-emitting device. In the embodiment, the intermediate layer may contain compound 1 and compound 2 as heterocyclic compounds. For example, compound 1 and compound 2 may be present in the same layer (for example, compound 1 and compound 2 may all be present in the emission layer), or may be present in different layers (for example, compound 1 may be present in the emission layer, and compound 2 may be present in the electron transport region).
[0208] The term “intermediate layer” as used herein may be a single layer and / or a plurality of layers between a first electrode and a second electrode of a light emitting device.
[0209] According to the embodiment, the electronic device may include a light emitting device. The electronic device may further include a thin film transistor. For example, the electronic device may further include a thin film transistor, the thin film transistor including a source electrode and a drain electrode, and the first electrode of the light emitting device may be electrically connected to the source electrode or the drain electrode. In the embodiment, the electronic device may further include a color filter, a color conversion layer, a touch screen layer, a polarization layer, or any combination thereof. The electronic device may be an electronic device as described herein.
[0210] [ Figure 1 Description]
[0211] Figure 1 1 is a schematic cross-sectional view of a light emitting device 10 according to the embodiment. The light emitting device 10 includes a first electrode 110 , an intermediate layer 130 , and a second electrode 150 .
[0212] In the following, refer to Figure 1 The structure of the light emitting device 10 and a method of manufacturing the light emitting device 10 according to the embodiment are described.
[0213] [First electrode 110]
[0214] exist Figure 1In the embodiment, the substrate may be further included below the first electrode 110 or above the second electrode 150. In the embodiment, the substrate may be a glass substrate or a plastic substrate. In the embodiment, the substrate may be a flexible substrate and may include a plastic having excellent heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.
[0215] The first electrode 110 may be formed by, for example, depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 may be a high work function material that facilitates hole injection.
[0216] The first electrode 110 may be a reflective electrode, a semi-transmissive reflective electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), or any combination thereof. In an embodiment, when the first electrode 110 is a semi-transmissive reflective electrode or a reflective electrode, the material used to form the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.
[0217] The first electrode 110 may have a structure consisting of a single layer or a structure including a plurality of layers. In the embodiment, the first electrode 110 may have a triple-layer structure of ITO / Ag / ITO.
[0218] [Middle layer 130]
[0219] The intermediate layer 130 may be disposed on the first electrode 110. The intermediate layer 130 may include an emission layer.
[0220] The intermediate layer 130 may further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 150 .
[0221] The intermediate layer 130 may further include a metal-containing compound (eg, an organic metal compound), an inorganic material (eg, quantum dots), and the like, in addition to various organic materials.
[0222] In an embodiment, the intermediate layer 130 may include two or more emission units stacked between the first electrode 110 and the second electrode 150, and at least one charge generation layer may be each between adjacent units in the two or more emission units. When the intermediate layer 130 includes two or more light-emitting units and at least one charge generation layer as described above, the light-emitting device 10 may be a tandem light-emitting device.
[0223] [Hole Transport Region in Intermediate Layer 130]
[0224] The hole transport region may have a single-layer structure consisting of a layer composed of a single material, a single-layer structure consisting of a layer containing different materials, or a multi-layer structure including a plurality of layers containing different materials.
[0225] The hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof.
[0226] In an embodiment, the hole transport zone may have a multilayer structure including a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission auxiliary layer structure, a hole injection layer / emission auxiliary layer structure, a hole transport layer / emission auxiliary layer structure, or a hole injection layer / hole transport layer / emission auxiliary layer structure, wherein the layers of each structure may be stacked from the first electrode 110 in their respective prescribed order, but the structure of the hole transport zone is not limited thereto.
[0227] The hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
[0228] [Formula 201]
[0229]
[0230] [Formula 202]
[0231]
[0232] In equation 201 and equation 202,
[0233] L 201 To L 204 may be each independently unsubstituted or substituted with at least one R 10a Substituted divalent C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted divalent C 1 -C 60 Heterocyclic groups,
[0234] L 205Can be *-O-*', *-S-*', *-N(Q 201 )-*', unsubstituted or replaced by at least one R 10a Substituted C 1 -C 20 Alkylene group, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 20 Alkenylene group, unsubstituted or substituted with at least one R 10a Substituted divalent C 3 -C 60 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted divalent C 1 -C 60 Heterocyclic group, * and *' each represent a bonding site with an adjacent atom,
[0235] xa1 to xa4 may each independently be an integer from 0 to 5,
[0236] xa5 can be an integer from 1 to 10,
[0237] R 201 To R 204 and Q 201 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic groups,
[0238] R 201 and R 202 may be optionally substituted via a single bond, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 5 The alkylene group is either unsubstituted or substituted with at least one R 10a Substituted C 2 -C 5 Alkenylene groups are linked to each other to form an unsubstituted or substituted 10a Substituted C 8 -C 60 Polycyclic groups (eg, carbazole groups) (eg, compound HT16).
[0239] R 203 and R 204 may be optionally substituted via a single bond, unsubstituted or substituted by at least one R 10a Substituted C 1 -C 5Alkylene groups, either unsubstituted or substituted with at least one R 10a Substituted C 2 -C 5 Alkenylene groups are linked to each other to form an unsubstituted or substituted 10a Substituted C 8 -C 60 Polycyclic groups, and
[0240] na1 can be an integer from 1 to 4. 10a Can be the same as described herein.
[0241] In an embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may include at least one of the groups represented by Formula CY201 to Formula CY217:
[0242]
[0243] Among them, in formula CY201 to formula CY217, R 10b and R 10c can be independently determined as 10a Description, Cyclic Cy 201 To Ring CY 204 Can be C independently 3 -C 20 Carbocyclic group or C 1 -C 20 heterocyclic group, and at least one hydrogen in Formula CY201 to Formula CY217 may be unsubstituted or replaced by R as described herein 10a replace.
[0244] In an embodiment, ring CY in formula CY201 to formula CY217 201 To Ring CY 204 Each may independently be a benzene group, a naphthyl group, a phenanthrene group or an anthracene group.
[0245] In the embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each independently include at least one of the groups represented by Formula CY201 to Formula CY203.
[0246] In an embodiment, the compound represented by Formula 201 may include at least one of the groups represented by Formula CY201 to Formula CY203 and at least one of the groups represented by Formula CY204 to Formula CY217.
[0247] In the embodiment, in Formula 201, xa1 may be 1, R 201 may be a group represented by one of the formulas CY201 to CY203, xa2 may be 0, and R 202It may be a group represented by one of Formula CY204 to Formula CY207.
[0248] In the embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include the group represented by Formula CY201 to Formula CY203.
[0249] In the embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include the group represented by Formula CY201 to Formula CY203, and may each independently include at least one of the groups represented by Formula CY204 to Formula CY217.
[0250] In the embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include the group represented by Formula CY201 to Formula CY217.
[0251] In an embodiment, the hole transport region may include one of compounds HT1 to HT47, 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), or any combination thereof:
[0252]
[0253]
[0254]
[0255]
[0256]
[0257] The thickness of the hole transport region may be about to about For example, the thickness of the hole transport region may be about to about When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer may be about to about And the thickness of the hole transport layer can be about to about For example, the thickness of the hole injection layer may be about to about For example, the thickness of the hole transport layer may be about to about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within the above-described ranges, satisfactory hole transport characteristics may be obtained without a significant increase in driving voltage.
[0258] The emission auxiliary layer can increase the light emission efficiency by compensating the optical resonance distance according to the wavelength of the light emitted by the emission layer, and the electron blocking layer can block the leakage of electrons from the emission layer to the hole transport region. The material that can be included in the hole transport region can be included in the emission auxiliary layer and the electron blocking layer.
[0259] [p-dopant]
[0260] In addition to these materials, the hole transport region may further contain a charge generating material for improving the conductive property. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region (eg, in the form of a single layer composed of the charge generating material).
[0261] The charge generating material may be, for example, a p-dopant.
[0262] For example, the lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant can be less than or equal to about -3.5 eV.
[0263] In an embodiment, the p-dopant may include a quinone derivative, a compound containing a cyano group, a compound including the element EL1 and the element EL2, or any combination thereof.
[0264] Examples of the quinone derivative may include TCNQ and F4-TCNQ.
[0265] Examples of the cyano group-containing compound may include HAT-CN and a compound represented by Formula 221.
[0266]
[0267] [Formula 221]
[0268]
[0269] In formula 221,
[0270] R 221 To R 223 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R10a Substituted C 1 -C 60 Heterocyclic group, R 10a can be the same as described herein, and
[0271] R 221 To R 223 At least one of them may be independently substituted by: a cyano group; -F; -Cl; -Br; -I; a C substituted by a cyano group, -F, -Cl, -Br, -I or any combination thereof 1 -C 20 Alkyl group; or any combination thereof substituted C 3 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic group.
[0272] In the compound including the element EL1 and the element EL2, the element EL1 may be a metal, a metalloid, or any combination thereof, and the element EL2 may be a nonmetal, a metalloid, or any combination thereof.
[0273] Examples of metals may include alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), etc. (e.g., tantalum (Tb), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.).
[0274] Examples of metalloids may include silicon (Si), antimony (Sb), and tellurium (Te).
[0275] Examples of non-metals may include oxygen (O) and halogens (eg, F, Cl, Br, I, etc.).
[0276] Examples of compounds containing element EL1 and element EL2 may include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides, metal iodides, etc.), metalloid halides (e.g., metalloid fluorides, metalloid chlorides, metalloid bromides, metalloid iodides, etc.), metal tellurides, or any combination thereof.
[0277] Examples of metal oxides may include tungsten oxides (eg, WO, W 2 O 3 , WO 2 , WO 3 , W 2 O 5 etc.), vanadium oxides (e.g., VO, V 2 O 3 , VO 2 、V 2 O 5 etc.), molybdenum oxides (e.g., MoO, Mo 2 O 3 、MoO 2 、MoO 3 、Mo 2 O 5 etc.) and rhenium oxides (e.g., ReO 3 wait).
[0278] Examples of the metal halide may include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, and lanthanide metal halides.
[0279] Examples of the alkali metal halide may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and CsI.
[0280] Examples of alkaline earth metal halides may include BeF 2 MgF 2 , CaF 2 , SrF 2 , BaF 2 、BeCl 2 MgCl 2 , CaCl 2 、SrCl 2 、BaCl 2 ,BeBr 2 MgBr 2 , CaBr 2 , SrBr 2 ,BaBr 2 ,BeI2 MgI 2 ,CaI 2 , SrI 2 and BaI 2 .
[0281] Examples of transition metal halides may include titanium halides (eg, TiF 4 、TiCl 4 、TiBr 4 、TiI 4 etc.), zirconium halides (e.g., ZrF 4 、ZrCl 4 , ZrBr 4 , ZrI 4 etc.), hafnium halides (e.g., HfF 4 , HfCl 4 , HfBr 4 , HfI 4 etc.), vanadium halides (e.g., VF 3 、VCl 3 , VBr 3 VI 3 etc.), niobium halides (e.g., NbF 3 、NbCl 3 , NbBr 3 , NbI 3 etc.), tantalum halides (e.g., TaF 3 、TaCl 3 、TaBr 3 、TaI 3 etc.), chromium halides (e.g., CrF 3 CrCl 3 CrBr 3 CrI 3 etc.), molybdenum halides (e.g., MoF 3 、MoCl 3 、MoBr 3 、MoI 3 etc.), tungsten halides (e.g., WF 3 、WCl 3 , WBr 3 , WI 3 etc.), manganese halides (e.g., MnF 2 、MnCl 2 、MnBr 2 、MnI 2 etc.), technetium halides (e.g., TcF 2 , TcCl 2 、TcBr 2 , TcI 2etc.), rhenium halides (e.g., ReF 2 、ReCl 2 、ReBr 2 、ReI 2 etc.), iron halides (e.g., FeF 2 、FeCl 2 , FeBr 2 ,FeI 2 etc.), ruthenium halides (e.g., RuF 2 、RuCl 2 ,RuBr 2 , RuI 2 etc.), osmium halides (e.g., OsF 2 , OsCl 2 、OsBr 2 , OsI 2 etc.), cobalt halides (e.g., CoF 2 、CoCl 2 ,CoBr 2 、CoI 2 etc.), rhodium halides (e.g., RhF 2 , RhCl 2 , RhBr 2 , RhI 2 etc.), iridium halides (e.g., IrF 2 、IrCl 2 ,IrBr 2 ,IrI 2 etc.), nickel halides (e.g., NiF 2 、NiCl 2 、NiBr 2 , NiI 2 etc.), palladium halides (e.g., PdF 2 , PdCl 2 , PdBr 2 , PdI 2 etc.), platinum halides (e.g., PtF 2 、PtCl 2 , PtBr 2 , PtI 2 etc.), copper halides (e.g., CuF, CuCl, CuBr, CuI, etc.), silver halides (e.g., AgF, AgCl, AgBr, AgI, etc.), gold halides (e.g., AuF, AuCl, AuBr, AuI, etc.).
[0282] Examples of late transition metal halides may include zinc halides (e.g., ZnF 2 、ZnCl 2 、ZnBr 2 、ZnI2 etc.), indium halides (e.g., InI 3 etc.) and tin halides (e.g., SnI 2 wait).
[0283] Examples of lanthanide metal halides may include YbF, YbF 2 , YbF 3 、SmF 3 , YbCl, YbCl 2 YbCl 3 、SmCl 3 , YbBr, YbBr 2 , YbBr 3 、SmBr 3 、YbI、YbI 2 ,YbI 3 and SmI 3 .
[0284] Examples of metalloid halides may include antimony halides (e.g., SbCl 5 wait).
[0285] Examples of metal tellurides may include alkali metal tellurides (eg, Li 2 Te、Na 2 Te, K 2 Te、Rb 2 Te, Cs 2 Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metal tellurides (e.g., TiTe 2 、ZrTe 2 、HfTe 2 、V 2 Te 3 , Nb 2 Te 3 、 2 Te 3 Cr 2 Te 3 、Mo 2 Te 3 , W 2 Te 3 , MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu 2 Te, CuTe, Ag 2 Te, AgTe, Au 2Te, etc.), late transition metal tellurides (e.g., ZnTe, etc.), and lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.).
[0286] [Emitting Layer in Intermediate Layer 130]
[0287] When the light-emitting device 10 is a full-color light-emitting device, the emission layer can be patterned into a red emission layer, a green emission layer and / or a blue emission layer according to the sub-pixel. In an embodiment, the emission layer may have a stacked structure of two or more layers of a red emission layer, a green emission layer and a blue emission layer, wherein the two or more layers may be in contact with each other or may be separated from each other to emit white light. In an embodiment, the emission layer may include two or more materials of a red light-emitting material, a green light-emitting material and a blue light-emitting material, wherein the two or more materials may be mixed with each other in a single layer to emit white light.
[0288] The emission layer may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.
[0289] The amount of the dopant in the emission layer may be about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host.
[0290] In an embodiment, the emissive layer may comprise quantum dots.
[0291] In an embodiment, the emissive layer may include a delayed fluorescent material. The delayed fluorescent material may be used as a host or a dopant in the emissive layer.
[0292] The thickness of the emission layer can be about to about For example, the thickness of the emission layer may be about to about When the thickness of the emission layer is within any of the ranges described above, excellent light emitting characteristics may be obtained without a significant increase in driving voltage.
[0293] [main body]
[0294] The host may include a compound represented by Formula 301:
[0295] [Formula 301]
[0296] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ]xb21
[0297] In formula 301,
[0298] Ar 301 may be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, L 301 may be unsubstituted or substituted with at least one R 10a Substituted divalent C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted divalent C 1 -C 60 Heterocyclic groups,
[0299] xb11 can be 1, 2 or 3,
[0300] xb1 can be an integer from 0 to 5.
[0301] R 301 It can be hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or replaced by at least one R 10a Substituted C 1 -C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C 2 -C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, -Si(Q 301 )(Q 302 )(Q 303 )、-N(Q 301 )(Q 302 )、-B(Q 301 )(Q 302 )、-C(=O)(Q301 )、-S(=O) 2 (Q 301 ) or -P(=O)(Q 301 )(Q 302 ),
[0302] xb21 can be an integer from 1 to 5, and
[0303] Q 301 To Q 303 can be independently determined as 1 Description of R 10a Can be the same as described herein.
[0304] In an embodiment, in Formula 301, when xb11 is 2 or greater, two or more Ar 301 can be connected to each other via a single bond.
[0305] In an embodiment, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
[0306] [Formula 301-1]
[0307]
[0308] [Formula 301-2]
[0309]
[0310] In Formula 301-1 and Formula 301-2,
[0311] Ring A 301 To Ring A 304 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, R 10a can be the same as described in this article,
[0312] X 301 Can be O, S, N[(L 304 ) xb4 -R 304 ]、C(R 304 )(R 305 ) or Si(R 304 )(R 305 ),
[0313] xb22 and xb23 can each independently be 0, 1 or 2,
[0314] L 301 , xb1 and R 301 may each independently be the same as described herein,
[0315] L 302 To L 304 can be independently related to L 301 Same as described,
[0316] xb2 to xb4 may each independently be the same as described with respect to xb1, and
[0317] R 302 To R 305 and R 311 To R 314 can be independently compared with R 301 Same as described.
[0318] In an embodiment, the host may include an alkaline earth metal complex, a late transition metal complex, or any combination thereof. In an embodiment, the host may include a Be complex (eg, compound H55), a Mg complex, a Zn complex, or any combination thereof.
[0319] In an embodiment, the host may include one of Compound H1 to Compound H129; 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-carbazolyl)benzene (mCP); 1,3,5-tri(carbazolyl-9-yl)benzene (TCP); or any combination thereof:
[0320]
[0321]
[0322]
[0323]
[0324]
[0325]
[0326]
[0327] [Phosphorescent dopant]
[0328] The phosphorescent dopant may include at least one transition metal as a central metal.
[0329] The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.
[0330] The phosphorescent dopant may be electrically neutral.
[0331] In an embodiment, the phosphorescent dopant may include an organometallic compound represented by Formula 401:
[0332] [Formula 401]
[0333] M(L 401 ) xc1 (L 402 ) xc2
[0334] [Formula 402]
[0335]
[0336] In equations 401 and 402,
[0337] M may be a transition metal (e.g., iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)),
[0338] L 401 may be a ligand represented by formula 402, and xc1 is 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,
[0339] L 402 can be an organic ligand, and xc2 can be 0, 1, 2, 3 or 4, wherein when xc2 is 2 or greater than 2, two or more L 402 can be the same or different from each other,
[0340] X 401 and X 402 may each independently be nitrogen or carbon,
[0341] Ring A 401 and Ring A 402 Can be C independently 3 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic groups,
[0342] T 401It 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=*', * and *' each represent a binding site with an adjacent atom,
[0343] X 403 and X 404 can each independently be a chemical bond (e.g., a covalent bond or a coordination bond), O, S, N (Q 413 )、B(Q 413 )、P(Q 413 )、C(Q 413 )(Q 414 ) or Si(Q 413 )(Q 414 ),
[0344] Q 411 To Q 414 can be independently related to Q 1 Same as described,
[0345] R 401 and R 402 can be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 20 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 20 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O) 2 (Q 401 ) or -P(=O)(Q401 )(Q 402 ),
[0346] Q 401 To Q 403 can be independently compared with 1 Same as described, R 10a can be the same as described in this article,
[0347] xc11 and xc12 may each independently be an integer from 0 to 10, and
[0348] * and *' in Formula 402 each represent a binding site with M in Formula 401.
[0349] In an embodiment, in Formula 402, X 401 can be nitrogen, and X 402 It can be carbon, or X 401 and X 402 Each may be nitrogen.
[0350] In an embodiment, in Formula 401, when xc1 is 2 or greater than 2, two or more L 401 The two rings A 401 Optionally, the linkage group may be T 402 connected together, and the two rings A 402 Optionally, the linkage group may be T 403 Connected together (see Compound PD1 to Compound PD4 and Compound PD7). 402 and T 403 can be independently compared with T 401 Same as described.
[0351] L in Formula 401 402 It can be an organic ligand. In an embodiment, L 402 It may include a halogen group, a diketone group (e.g., an acetylacetonate group), a carboxylic acid group (e.g., a picolinate group), -C(=O), an isonitrile group, -CN, a phosphorus-containing group (e.g., a phosphine group, a phosphite group, etc.), or any combination thereof.
[0352] The phosphorescent dopant may include, for example, one of Compound PD1 to Compound PD39 or any combination thereof:
[0353]
[0354]
[0355]
[0356] [Fluorescent dopant]
[0357] The fluorescent dopant may include an amine group-containing compound, a styryl group-containing compound, or any combination thereof.
[0358] In an embodiment, the fluorescent dopant may include a compound represented by Formula 501:
[0359] [Formula 501]
[0360]
[0361] In formula 501,
[0362] Ar 501 , R 501 and R 502 may be each independently unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, L 501 To L 503 may be each independently unsubstituted or substituted with at least one R 10a Substituted divalent C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted divalent C 1 -C 60 Heterocyclic groups,
[0363] xd1 to xd3 may each independently be 0, 1, 2 or 3, and
[0364] xd4 can be 1, 2, 3, 4, 5 or 6.
[0365] In an embodiment, in Formula 501, Ar 501 It may be a fused cyclic group in which three or more monocyclic groups are fused together (for example, anthracene groups, group, pyrene group, etc.).
[0366] In an embodiment, in Formula 501, xd4 can be 2.
[0367] In an embodiment, the fluorescent dopant may include one of compounds FD1 to FD37, DPVBi, DPAVBi, or any combination thereof:
[0368]
[0369]
[0370]
[0371]
[0372] [Delayed fluorescence material]
[0373] The emitting layer may contain a delayed fluorescent material.
[0374] The delayed fluorescent material may be selected from compounds capable of emitting delayed fluorescence based on a delayed fluorescence emission mechanism.
[0375] The delayed fluorescent material included in the emission layer may serve as a host or a dopant depending on the types of other materials included in the emission layer.
[0376] In the embodiment, the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material may be about 0 eV to about 0.5 eV. When the difference between the triplet energy level (eV) of the delayed fluorescent material and the singlet energy level (eV) of the delayed fluorescent material satisfies the range described above, the up-conversion of the delayed fluorescent material from the triplet state to the singlet state may effectively occur, and thus the light-emitting device 10 may have improved luminous efficiency.
[0377] In an embodiment, the delayed fluorescent material may include: a molecule including at least one electron donor (eg, a π-electron-rich C 3 -C 60 a cyclic group, such as a carbazole group) and at least one electron acceptor (e.g., a sulfoxide group, a cyano group, a π-electron-deficient nitrogen-containing C 1 -C 60 or a C-containing material comprising at least two cyclic groups fused to each other and sharing boron (B) 8 -C 60 Polycyclic materials.
[0378] In an embodiment, the delayed fluorescent material may include at least one of Compound DF1 to Compound DF14:
[0379]
[0380]
[0381] [Quantum dot]
[0382] In an embodiment, the emissive layer may comprise quantum dots.
[0383] In the specification, "quantum dot" may be a crystal of a semiconductor compound and may include any material capable of emitting light of various emission wavelengths according to the size of the crystal. The quantum dot may emit light of various emission wavelengths by adjusting the ratio of elements within the quantum dot.
[0384] The diameter of the quantum dot can be, for example, about 1 nm to about 10 nm.
[0385] Quantum dots can be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, or any process similar thereto.
[0386] The wet chemical process is a method that includes mixing a precursor material with an organic solvent and growing a quantum dot particle crystal. As the crystal grows, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot crystal and controls the growth of the crystal, so that the growth of the quantum dot particles can be controlled by a process that is less expensive and can be more easily performed than a vapor deposition method such as metal organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE).
[0387] Quantum dots may include: Group II-VI semiconductor compounds; Group III-V semiconductor compounds; Group III-VI semiconductor compounds; Group I-III-VI semiconductor compounds; Group IV-VI semiconductor compounds; Group IV elements or compounds; or any combination thereof.
[0388] Examples of II-VI semiconductor compounds may include binary compounds such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, or MgS; ternary compounds such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, Cd ... dZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe or MgZnS; a quaternary compound, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe or HgZnSTe; or any combination thereof.
[0389] Examples of III-V semiconductor compounds may include binary compounds such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, etc.; ternary compounds such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, InPSb, etc.; quaternary compounds such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, etc.; or any combination thereof. In an embodiment, the III-V semiconductor compound may further include a Group II element. Examples of the Group III-V semiconductor compound further including the Group II element may include InZnP, InGaZnP, and InAlZnP.
[0390] Examples of III-VI semiconductor compounds may include binary compounds such as GaS, GaSe, Ga 2 Se 3 、GaTe、InS、InSe、In 2 S 3 、In 2 Se 3 or InTe; ternary compounds such as InGaS 3 or InGaSe 3 ; or any combination thereof.
[0391] Examples of Group I-III-VI semiconductor compounds may include: ternary compounds such as AgInS, AgInS 2 、AgInSe 2 、AgGaS、AgGaS 2 、AgGaSe 2 、CuInS、CuInS 2 、CuInSe 2 、CuGaS 2 、CuGaSe 2 、CuGaO 2 、CuGaO 2 、AgGaO 2 、AgAlO 2 etc.; quaternary compounds, such as AgInGaS 2 、AgInGaSe 2etc.; or any combination thereof.
[0392] Examples of IV-VI semiconductor compounds may include: binary compounds, such as SnS, SnSe, SnTe, PbS, PbSe or PbTe; ternary compounds, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe or SnPbTe; quaternary compounds, such as SnPbSSe, SnPbSeTe or SnPbSTe; or any combination thereof.
[0393] Examples of Group IV elements or compounds may include: a single element, such as Si or Ge; a binary compound, such as SiC or SiGe; or any combination thereof.
[0394] Each element contained in a multi-element compound (e.g., a binary compound, a ternary compound, or a quaternary compound) may be present in the particle in a uniform concentration or a non-uniform concentration. For example, the above formula may refer to the type of element contained in the compound, wherein the ratio of the elements in the compound may vary. For example. AgInGaS 2 Can refer to AgIn x Ga 1-x S 2 (where x is a real number between 0 and 1).
[0395] In an embodiment, the quantum dot may have a single structure in which the concentration of each element in the quantum dot is uniform, or may have a core-shell structure. In an embodiment, the material contained in the core and the material contained in the shell may be different from each other.
[0396] The shell of a quantum dot can be used as a protective layer to prevent chemical denaturation of the core to maintain semiconductor properties and / or can be used as a charging layer to impart electrophoretic properties to the quantum dot. The shell can be a single layer or multiple layers. The interface between the core and the shell can have a concentration gradient, where the concentration of the material present in the shell decreases toward the core.
[0397] Examples of metals forming the shell of quantum dots may include metal oxides, metalloid oxides or non-metal oxides, semiconductor compounds or any combination thereof. Examples of metal oxides, metalloid oxides or non-metal oxides may include: binary compounds, such as SiO 2 、Al 2 O 3 、TiO 2 、ZnO、MnO、Mn 2 O 3 , Mn 3 O 4 , CuO, FeO, Fe 2 O 3, Fe 3 O 4 , CoO, Co 3 O 4 or NiO; ternary compounds such as MgAl 2 O 4 、CoFe 2 O 4 、NiFe 2 O 4 or CoMn 2 O 4 ; or any combination thereof. Examples of semiconductor compounds may include: II-VI semiconductor compounds; III-V semiconductor compounds; III-VI semiconductor compounds; I-III-VI semiconductor compounds; IV-VI semiconductor compounds; or any combination thereof. Examples of semiconductor compounds may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.
[0398] The quantum dots may have a full width at half maximum (FWHM) of an emission wavelength spectrum less than or equal to about 45 nm. For example, the quantum dots may have a FWHM of an emission wavelength spectrum less than or equal to about 40 nm. For example, the quantum dots may have a FWHM of an emission wavelength spectrum less than or equal to about 30 nm. When the FWHM of the quantum dots is within any of these ranges, the quantum dots may have improved color purity or improved color reproducibility. The light emitted by the quantum dots may be emitted in all directions, so that the wide viewing angle may be improved.
[0399] In embodiments, the quantum dots may be in the form of spherical particles, pyramidal particles, multi-arm particles, or cubic particles, or the quantum dots may be in the form of nanoparticles, nanotubes, nanowires, nanofibers, or nanoplates.
[0400] Since the band gap can be adjusted by controlling the size of the quantum dots, light with various wavelength bands can be obtained from the quantum dot emission layer. Therefore, by using quantum dots of different sizes, a light-emitting device that emits light of various wavelengths can be realized. The size of the quantum dots or the ratio of the elements in the quantum dot compound can be selected to emit red light, green light and / or blue light. In an embodiment, the quantum dots can be configured to emit white light by a combination of various colors of light.
[0401] [Electron Transport Region in Intermediate Layer 130]
[0402] The electron transport region may have a single-layer structure consisting of a layer composed of a single material, a single-layer structure consisting of layers including different materials, or a multi-layer structure including a plurality of layers including different materials.
[0403] The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0404] In an embodiment, the electron transport zone may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein the layers of each structure may be stacked from the emission layer in their respective prescribed order, but the structure of the electron transport zone is not limited thereto.
[0405] In an embodiment, the electron transport region (eg, a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a nitrogen-containing C 1 -C 60 Metal-free compounds of cyclic groups.
[0406] In an embodiment, the electron transport region may include a compound represented by Formula 601.
[0407] [Formula 601]
[0408] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21
[0409] In formula 601,
[0410] Ar 601 may be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, L 601 may be unsubstituted or substituted with at least one R 10a Substituted divalent C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted divalent C 1 -C 60 Heterocyclic groups,
[0411] xe11 can be 1, 2 or 3,
[0412] xe1 can be 0, 1, 2, 3, 4, or 5,
[0413] R 601 may be unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group, -Si(Q 601 )(Q 602 )(Q 603 )、-C(=O)(Q 601 )、-S(=O) 2 (Q 601 ) or -P(=O)(Q 601 )(Q 602 ),
[0414] Q 601 To Q 603 can be independently compared with this article on Q 1 Same as described,
[0415] xe21 can be 1, 2, 3, 4, or 5, and
[0416] At least one of the following conditions can be met: 601 may be unsubstituted or substituted with at least one R 10a Substituted π-electron-deficient nitrogen-containing C 1 -C 60 Cyclic group; R 601 may be unsubstituted or substituted with at least one R 10a Substituted π-electron-deficient nitrogen-containing C 1 -C 60 A cyclic group; and L 601 may be unsubstituted or substituted with at least one R 10a Substituted divalent π-electron-deficient nitrogen-containing C 1 -C 60 Cyclic group.
[0417] In an embodiment, in Formula 601, when xe11 is 2 or greater than 2, two or more Ar 601 Can be connected together via a single bond.
[0418] In an embodiment, in Formula 601, Ar 601 may be unsubstituted or substituted with at least one R 10a Substituted anthracene group. 10a Can be the same as described herein.
[0419] In an embodiment, the electron transport region may include a compound represented by Formula 601-1:
[0420] [Formula 601-1]
[0421]
[0422] In formula 601-1,
[0423] 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 X 614 To X 616 At least one of can each be N,
[0424] L 611 To L 613 can be independently related to L 601 Same as described,
[0425] xe611 to xe613 can each independently be the same as described for xe1,
[0426] R 611 To R 613 can be independently compared with R 601 Same as described, and
[0427] R 614 To R 616 can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C 3 -C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 60 Heterocyclic group. 10a Can be the same as described herein.
[0428] In an embodiment, in Formula 601 and Formula 601-1, xe1 and xe611 to xe613 may each independently be 0, 1 or 2.
[0429] The electron transport region may include compounds ET1 to ET46, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq 3 , BAlq, TAZ, NTAZ or any combination thereof:
[0430]
[0431]
[0432]
[0433] The thickness of the electron transport region may be about to about For example, the thickness of the electron transport region may be about to about When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron control layer may be each independently about to about And the thickness of the electron transport layer can be about to about For example, the thickness of the buffer layer, the hole blocking layer, or the electron control layer can each independently be about to about For example, the thickness of the electron transport layer may be about to about When the thickness of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer and / or the electron transport region is within these ranges, satisfactory electron transport characteristics may be obtained without a significant increase in driving voltage.
[0434] The electron transport region (eg, an electron transport layer in the electron transport region) may further include a metal-containing material in addition to the materials described above.
[0435] The metal-containing material can include alkali metal complex, alkaline earth metal complex or its any combination. The metal ion of alkali metal complex can be Li ion, Na ion, K ion, Rb ion or Cs ion, and the metal ion of alkaline earth metal complex can be Be ion, Mg ion, Ca ion, Sr ion or Ba ion. The ligand coordinated with the metal ion of alkali metal complex or alkaline earth metal complex can independently include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene or its any combination.
[0436] In an embodiment, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1(Liq) or compound ET-D2:
[0437]
[0438] The electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer may contact (e.g., directly contact) the second electrode 150.
[0439] The electron injection layer may have: a single-layer structure composed of a layer composed of a single material, a single-layer structure composed of layers containing different materials, or a multi-layer structure including multiple layers containing different materials.
[0440] The electron injection layer may contain an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
[0441] The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
[0442] The alkali metal-containing compound, the alkaline earth metal-containing compound, and the rare earth metal-containing compound may contain oxides, halides (e.g., fluorides, chlorides, bromides, iodides, etc.) or tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, or any combination thereof.
[0443] The alkali metal-containing compound may include: alkali metal oxides, such as Li 2 O, Cs 2 O, or K 2 O; alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI; or any combination thereof. The alkaline earth metal-containing compound may include alkaline earth metal oxides, such as BaO, SrO, CaO, Ba x Sr 1-x O (x is a real number satisfying 0 < x < 1) or Ba x Ca 1-x O (x is a real number satisfying 0 < x < 1). The rare earth metal-containing compound may include YbF 3 、ScF 3 、Sc 2 O 3 、Y 2 O 3、Ce 2 O 3 , GdF 3 , TbF 3 ,YbI 3 ScI 3 , TbI 3 Or any combination thereof. In an embodiment, the rare earth metal-containing compound may include a lanthanide metal telluride. Examples of lanthanide metal tellurides may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, LaTe, 2 Te 3 、Ce 2 Te 3 , Pr 2 Te 3 、Nd 2 Te 3 、Pm 2 Te 3 、Sm 2 Te 3 、Eu 2 Te 3 , Gd 2 Te 3 , Tb 2 Te 3 、Dy 2 Te 3 、Ho 2 Te 3 , Er 2 Te 3 、Tm 2 Te 3 , Yb 2 Te 3 He Lu 2 Te 3 .
[0444] The alkali metal complex, alkaline earth metal complex and rare earth metal complex may contain: an alkali metal ion, an alkaline earth metal ion or a rare earth metal ion; and a ligand bonded to the metal ion, such as hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene or any combination thereof.
[0445] The electron injection layer may be composed of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof as described above. In an embodiment, the electron injection layer may further include an organic material (e.g., a compound represented by Formula 601).
[0446] In an embodiment, the electron injection layer may be composed of an alkali metal-containing compound (e.g., an alkali metal halide), or the electron injection layer may be composed of an alkali metal-containing compound (e.g., an alkali metal halide) and an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. In an embodiment, the electron injection layer may be a KI:Yb co-deposition layer, a RbI:Yb co-deposition layer, a LiF:Yb co-deposition layer, etc.
[0447] When the electron injection layer further comprises an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex or any combination thereof can be uniformly or non-uniformly dispersed in a matrix comprising an organic material.
[0448] The thickness of the electron injection layer can be about to about For example, the thickness of the electron injection layer may be about to about When the thickness of the electron injection layer is within any range as described above, satisfactory electron injection characteristics may be obtained without a significant increase in driving voltage.
[0449] [Second electrode 150]
[0450] The second electrode 150 may be disposed on the intermediate layer 130. The second electrode 150 may be a cathode as an electron injection electrode. When the second electrode 150 is a cathode, a material for forming the second electrode 150 may include a material having a low work function, such as a metal, an alloy, a conductive compound, or any combination thereof.
[0451] The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO or any combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive reflective electrode or a reflective electrode.
[0452] The second electrode 150 may have a single-layer structure or a multi-layer structure.
[0453] [Overlay]
[0454] The light emitting device 10 may include a first covering layer outside the first electrode 110 and / or a second covering layer outside the second electrode 150. In the embodiment, the light emitting device 10 may have a structure in which the first covering layer, the first electrode 110, the intermediate layer 130, and the second electrode 150 are stacked in this specified order, a structure in which the first electrode 110, the intermediate layer 130, the second electrode 150 and the second covering layer are stacked in this specified order, or a structure in which the first covering layer, the first electrode 110, the intermediate layer 130, the second electrode 150 and the second covering layer are stacked in this specified order.
[0455] The light generated in the emission layer of the intermediate layer 130 of the light emitting device 10 can be led out to the outside through the first electrode 110 (which can be a semi-transmissive reflective electrode or a transmissive electrode) and through the first cover layer. The light generated in the emission layer of the intermediate layer 130 of the light emitting device 10 can be led out to the outside through the second electrode 150 (which can be a semi-transmissive reflective electrode or a transmissive electrode) and through the second cover layer.
[0456] The first cover layer and the second cover layer can each increase the external emission efficiency according to the principle of constructive interference, thereby increasing the light extraction efficiency of the light emitting device 10, so that the light emitting efficiency of the light emitting device 10 can be increased.
[0457] The first cover layer and the second cover layer may each include a material having a refractive index greater than or equal to about 1.6 (with respect to a wavelength of about 589 nm).
[0458] The first covering layer and the second covering layer may each independently be an organic covering layer including an organic material, an inorganic covering layer including an inorganic material, or an organic-inorganic composite covering layer including an organic material and an inorganic material.
[0459] At least one of the first covering layer and the second covering layer may each independently contain a carbocyclic compound, a heterocyclic compound, a compound containing an amine group, a porphyrin derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the compound containing an amine group may each be optionally substituted with a substituent containing O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof.
[0460] In an embodiment, at least one of the first cover layer and the second cover layer may each independently include a compound containing an amine group.
[0461] In an embodiment, at least one of the first cover layer and the second cover layer may each independently include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.
[0462] In an embodiment, at least one of the first cover layer and the second cover layer may each independently include one of Compound HT28 to Compound HT33, one of Compound CP1 to Compound CP6, β-NPB, or any combination thereof:
[0463]
[0464] [membrane]
[0465] The heterocyclic compound represented by Formula 1 can be included in various films. Therefore, another embodiment provides a film comprising a heterocyclic compound represented by Formula 1. The film can be, for example, an optical member (or light control mechanism) (e.g., a color filter, a color conversion member, a cover layer, a light extraction efficiency enhancement layer, a selective light absorption layer, a polarization layer, a layer containing quantum dots, etc.), a light blocking member (e.g., a light reflecting layer, a light absorbing layer, etc.), or a protective member (e.g., an insulating layer, a dielectric layer, etc.).
[0466] [Electronic equipment]
[0467] The light emitting device may be included in various electronic devices. For example, the electronic device including the light emitting device may be a light emitting device, an authentication device, etc.
[0468] In addition to the light-emitting device, the electronic device (e.g., light-emitting device) may further include a color filter, a color conversion layer, or a color filter and a color conversion layer. The color filter and / or the color conversion layer may be arranged in at least one direction of travel of the light emitted from the light-emitting device. For example, the light emitted from the light-emitting device may be blue light or white light. The light-emitting device may be a light-emitting device as described herein. In an embodiment, the color conversion layer may include quantum dots. The quantum dots may be, for example, quantum dots as described herein.
[0469] The electronic device may include a first substrate. The first substrate may include sub-pixels, the color filter may include color filter regions respectively corresponding to the sub-pixels, and the color conversion layer may include color conversion regions respectively corresponding to the sub-pixels.
[0470] A pixel defining film may be disposed between the sub-pixel regions to define each sub-pixel.
[0471] The color filter may further include color filter regions and a light shielding pattern disposed between the color filter regions, and the color conversion layer may further include a color conversion region and a light shielding pattern disposed between the color conversion regions.
[0472] The color filter region (or color conversion region) may include a first region emitting a first color light, a second region emitting a second color light, and / or a third region emitting a third color light, wherein the first color light, the second color light, and / or the third color light may have different maximum emission wavelengths from each other. In an embodiment, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. In an embodiment, the color filter region (or color conversion region) may include quantum dots. In an embodiment, the first region may include red quantum dots, the second region may include green quantum dots, and the third region may not include quantum dots. The quantum dots may be quantum dots as described herein. The first region, the second region, and / or the third region may each further include a scatterer.
[0473] In an embodiment, the light emitting device may emit a first light, the first region may absorb the first light to emit a first-first color light, the second region may absorb the first light to emit a second-first color light, and the third region may absorb the first light to emit a third-first color light. The first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths from each other. In an embodiment, the first light may be blue light, the first-first color light may be red light, the second-first color light may be green light, and the third-first color light may be blue light.
[0474] In addition to the light emitting device described above, the electronic device may further include a thin film transistor. The thin film transistor may include a source electrode, a drain electrode and an active layer, wherein any one of the source electrode and the drain electrode may be electrically connected to any one of the first electrode and the second electrode of the light emitting device.
[0475] The thin film transistor may further include a gate electrode, a gate insulating film, and the like.
[0476] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, or the like.
[0477] The electronic device may further include a sealing portion for sealing the light emitting device. The sealing portion may be arranged between the color filter and / or the color conversion layer and the light emitting device. The sealing portion allows light from the light emitting device to be led out to the outside, and may prevent ambient air and moisture from penetrating into the light emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin film encapsulation layer including at least one of an organic layer and an inorganic layer. When the sealing portion is a thin film encapsulation layer, the electronic device may be flexible.
[0478] Depending on the purpose of the electronic device, in addition to the color filter and / or color conversion layer, various functional layers may be further included on the sealing portion. Examples of functional layers may include a touch screen layer and a polarizing layer. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer. The verification device may be, for example, a biometric verification device that verifies an individual by using biometric information (e.g., fingertips, pupils, etc.) of a living being.
[0479] In addition to the light emitting device as described above, the authentication device may further include a biometric information collector.
[0480] The electronic device can be applied to various displays, light sources, lighting equipment, personal computers (for example, mobile personal computers), mobile phones, digital cameras, electronic notepads, electronic dictionaries, electronic game consoles, medical instruments (for example, electronic thermometers, blood pressure meters, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram displays, ultrasonic diagnostic devices or endoscope displays), fish finders, various measuring instruments, meters (for example, meters used for vehicles, aircraft and ships), projectors, etc.
[0481] [Electronic devices]
[0482] The light emitting device may be included in various electronic devices.
[0483] In an embodiment, the electronic device comprising the light emitting device can be a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a retractable display, a laser printer, a telephone, a mobile phone, a tablet personal computer, a tablet phone, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a three-dimensional (3D) display, a virtual reality display, an augmented reality display, a vehicle, a video wall comprising multiple displays stitched together, a theater screen, a stadium screen, a light therapy device, or a sign.
[0484] Since the light emitting device may have excellent effects in terms of light emitting efficiency and long lifespan, an electronic device including the light emitting device may have characteristics of high brightness, high resolution, and low power consumption.
[0485] [ Figure 2 and Figure 3 Description]
[0486] Figure 2 is a schematic cross-sectional view of an electronic device according to an embodiment.
[0487] Figure 2The electronic device (eg, a light emitting device) may include a substrate 100, a thin film transistor (TFT), a light emitting device, and an encapsulation part 300 that seals the light emitting device.
[0488] The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. The buffer layer 210 may be disposed on the substrate 100. The buffer layer 210 may prevent impurities from penetrating through the substrate 100 and may provide a flat surface on the substrate 100.
[0489] The TFT may be disposed on the buffer layer 210. The TFT may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
[0490] The active layer 220 may include an inorganic semiconductor (eg, silicon or polysilicon), an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.
[0491] A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be disposed on the active layer 220 , and the gate electrode 240 may be disposed on the gate insulating film 230 .
[0492] Interlayer insulating film 250 may be disposed on gate electrode 240. Interlayer insulating film 250 may be disposed between gate electrode 240 and source electrode 260 to insulate gate electrode 240 from source electrode 260 and between gate electrode 240 and drain electrode 270 to insulate gate electrode 240 from drain electrode 270.
[0493] Source electrode 260 and drain electrode 270 may be disposed on interlayer insulating film 250. Interlayer insulating film 250 and gate insulating film 230 may be formed to expose source and drain regions of active layer 220, and source electrode 260 and drain electrode 270 may contact exposed portions of the source and drain regions of active layer 220, respectively.
[0494] The TFT may be electrically connected to the light emitting device to drive the light emitting device, and may be covered and protected by the passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. A light emitting device may be provided on the passivation layer 280. The light emitting device may include a first electrode 110, an intermediate layer 130, and a second electrode 150.
[0495] The first electrode 110 may be disposed on the passivation layer 280. The passivation layer 280 may not completely cover the drain electrode 270 and may expose a portion of the drain electrode 270. The first electrode 110 may be electrically connected to the exposed portion of the drain electrode 270.
[0496] A pixel defining film 290 including an insulating material may be disposed on the first electrode 110. The pixel defining film 290 may expose a region of the first electrode 110, and the intermediate layer 130 may be formed on the exposed region of the first electrode 110. The pixel defining film 290 may be a polyimide-based organic film or a polyacrylic acid-based organic film. Figure 2 Although not shown in the figure, at least some layers of the intermediate layer 130 may extend beyond the upper portion of the pixel defining film 290 to be provided in the form of a common layer.
[0497] The second electrode 150 may be disposed on the intermediate layer 130, and the capping layer 170 may be further included on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.
[0498] The encapsulation part 300 may be located on the cover layer 170. The encapsulation part 300 may be located on the light emitting device to protect the light emitting device from moisture and / or oxygen. The encapsulation part 300 may include an inorganic film including silicon nitride (SiN x ), silicon oxide (SiO x ), indium tin oxide, indium zinc oxide or any combination thereof; an organic film comprising polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyvinyl sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic-based resin (e.g., polymethyl methacrylate, polyacrylic acid, etc.), an epoxy-based resin (e.g., aliphatic glycidyl ether (AGE), etc.) or any combination thereof; or any combination of an inorganic film and an organic film.
[0499] Figure 3 is a schematic cross-sectional view of an electronic device according to another embodiment.
[0500] Figure 3 An electronic device (eg, a light emitting device) may be used with Figure 2 The electronic device is different from the electronic device of the present invention in that at least the light shielding pattern 500 and the functional area 400 are further included outside the packaging part 300. The functional area 400 can be a color filter area, a color conversion area, or a combination of a color filter area and a color conversion area. Figure 3 The light-emitting device in the electronic device may be a series light-emitting device.
[0501] [ Figure 4 Description]
[0502] Figure 41 is a schematic perspective view of an electronic device 1 including a light-emitting device according to an embodiment. The electronic device 1 can be a device for displaying moving images or still images, and can be not only a portable electronic device, such as a mobile phone, a smart phone, a tablet personal computer (PC), a mobile communication terminal, an electronic log, an e-book, a portable multimedia player (PMP), a navigation device or an ultra-mobile PC (UMPC), but also various products, such as a television (TV), a laptop computer, a monitor, a billboard or an Internet of Things (IoT) device. The electronic device 1 can be any product or a component thereof as described above. The electronic device 1 can be a wearable device (such as a smart watch, a watch phone, a glasses-type display or a head-mounted display (HMD)) or a component of a wearable device. However, the embodiment is not limited thereto.
[0503] For example, the electronic device 1 may be a dashboard of a vehicle, a center panel of a vehicle, a central information display arranged on the dashboard of a vehicle, an interior mirror display of a vehicle replacing a side mirror, an entertainment display for a rear seat of a vehicle or arranged on the back of a front seat, or a head-up display (HUD) installed in front of the vehicle or projected on the front windshield, a computer-generated holographic augmented reality head-up display (CGH AR HUD). For ease of explanation, Figure 4 An embodiment is illustrated in which the electronic device 1 is a smartphone.
[0504] The electronic device 1 may include a display area DA and a non-display area NDA outside the display area DA. The display device may realize an image through a two-dimensional array of pixels arranged in the display area DA.
[0505] The non-display area NDA may be an area where an image is not displayed, and may surround (e.g., completely surround) the display area DA. A driver for providing an electrical signal or power to a display device arranged in the display area DA may be arranged on the non-display area NDA. A pad may be arranged in the non-display area NDA, the pad being an area to which an electronic component or a printed circuit board may be electrically connected.
[0506] In the electronic device 1, the length in the x-axis direction and the length in the y-axis direction may be different from each other. Figure 4 , the length in the x-axis direction may be less than the length in the y-axis direction. In an embodiment, the length in the x-axis direction may be the same as the length in the y-axis direction. In an embodiment, the length in the x-axis direction may be longer than the length in the y-axis direction.
[0507] [ Figure 5 and FIG. 6A to FIG. 6C Description]
[0508] Figure 5is a schematic perspective view of the exterior of a vehicle 1000 as an electronic device including a light emitting device according to the embodiment. FIG. 6A to FIG. 6C Each is a schematic diagram of the interior of a vehicle 1000 according to an embodiment.
[0509] refer to Figure 5 , Fig. 6A , Figure 6B and Figure 6C , the embodiment of the vehicle 1000 may include various devices for moving a transported object such as a person, an object, or an animal from a departure point to a destination point. Examples of the vehicle 1000 may include vehicles traveling on roads or tracks, ships moving on the sea or rivers, and airplanes flying in the air using the action of air.
[0510] The vehicle 1000 can travel on a road or a track. The vehicle 1000 can move in a selectable direction according to the rotation of at least one wheel. Examples of the vehicle 1000 may include a three-wheeled or four-wheeled vehicle, a construction machine, a two-wheeled vehicle, a prime mover, a bicycle, and a train traveling on a track.
[0511] The vehicle 1000 may include a vehicle body having an interior and an exterior, and a chassis, which is a part other than the body in which a machine device for driving is installed. The exterior of the vehicle body may include a front plate, a bonnet, a top plate, a rear plate, a luggage compartment, and pillars provided at the boundaries between doors, etc. The chassis of the vehicle 1000 may include a power generation device, a power transmission device, a drive device, a steering device, a brake device, a suspension device, a transmission device, a fuel device, front and rear wheels, left and right wheels, etc.
[0512] The vehicle 1000 may include side windows 1100 , a front window 1200 , side mirrors 1300 , a cluster piece 1400 , a center panel 1500 , a passenger seat instrument panel 1600 , and a display device 2 .
[0513] The side window glass 1100 and the front window glass 1200 may be separated by pillars disposed between the side window glass 1100 and the front window glass 1200 .
[0514] The side window glass 1100 may be mounted on the side of the vehicle 1000. In an embodiment, the side window glass 1100 may be mounted on a door of the vehicle 1000. A plurality of side window glasses 1100 may be provided and may face each other. In an embodiment, the side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In an embodiment, the first side window glass 1110 may be arranged adjacent to the cluster piece 1400, and the second side window glass 1120 may be arranged adjacent to the passenger seat instrument panel 1600.
[0515] In an embodiment, the side window glass 1100 may be spaced apart from each other in the x direction or the -x direction. In an embodiment, the first side window glass 1110 and the second side window glass 1120 may be spaced apart from each other in the x direction or the -x direction. For example, the virtual straight line L connecting the side window glass 1100 may extend in the x direction or the -x direction. In an embodiment, the virtual straight line L connecting the first side window glass 1110 and the second side window glass 1120 may extend in the x direction or the -x direction.
[0516] The front window glass 1200 may be installed at the front of the vehicle 1000. The front window glass 1200 may be disposed between the side window glasses 1100 facing each other.
[0517] The side view mirror 1300 can provide a rear view of the vehicle 1000. The side view mirror 1300 can be installed on the outside of the vehicle body. In an embodiment, a plurality of side view mirrors 1300 can be provided. One of the side view mirrors 1300 can be arranged outside the first side window glass 1110, and another of the side view mirrors 1300 can be arranged outside the second side window glass 1120.
[0518] Cluster piece 1400 may be arranged in front of the steering wheel. Cluster piece 1400 may include a tachometer, a speedometer, a coolant temperature gauge, a fuel gauge, a turn indicator, a high beam indicator, a warning light, a seat belt warning light, an odometer, a speedometer, an automatic transmission selector indicator light, a door open warning light, an oil warning light, and / or a low fuel warning light.
[0519] The center panel 1500 may include a control panel on which buttons for adjusting an audio device, an air conditioning device, and a seat heater are provided. The center panel 1500 may be disposed on one side of the cluster piece 1400 .
[0520] The passenger seat instrument panel 1600 may be spaced apart from the cluster piece 1400 with the center panel 1500 disposed therebetween. In an embodiment, the cluster piece 1400 may be disposed to correspond to a driver seat (not shown), and the passenger seat instrument panel 1600 may be disposed to correspond to a passenger seat (not shown). In an embodiment, the cluster piece 1400 may be adjacent to the first side window glass 1110, and the passenger seat instrument panel 1600 may be adjacent to the second side window glass 1120.
[0521] In an embodiment, the display device 2 may include a display panel 3, and the display panel 3 may display an image. The display device 2 may be arranged inside the vehicle 1000. In an embodiment, the display device 2 may be arranged between the side window glasses 1100 facing each other. The display device 2 may be arranged on at least one of the cluster member 1400, the center panel 1500, and the passenger seat instrument panel 1600.
[0522] The display device 2 may include an organic light emitting display, an inorganic electroluminescent display, a quantum dot display, etc. Hereinafter, as the display device 2 according to the embodiment, the organic light emitting display device including the light emitting device according to the embodiment will be described as an example. However, various types of display devices as described above may be used in the embodiment.
[0523] refer to Fig. 6A , the display device 2 may be arranged on the central panel 1500. In an embodiment, the display device 2 may display navigation information. In an embodiment, the display device 2 may display information about audio settings, video settings, or vehicle settings.
[0524] refer to Figure 6B , the display device 2 may be arranged on the clusterware 1400. The clusterware 1400 may display driving information and the like through the display device 2. For example, the clusterware 1400 may digitally implement driving information. The clusterware 1400 may display vehicle information and driving information as images. In an embodiment, the needle and gauge of a tachometer and various warning light icons may be displayed through digital signals.
[0525] refer to Figure 6C , the display device 2 may be arranged on the passenger seat instrument panel 1600. The display device 2 may be embedded in the passenger seat instrument panel 1600 or arranged on the passenger seat instrument panel 1600. In an embodiment, the display device 2 arranged on the passenger seat instrument panel 1600 may display an image related to the information displayed on the cluster piece 1400 and / or the information displayed on the center panel 1500. In an embodiment, the display device 2 arranged on the passenger seat instrument panel 1600 may display information different from the information displayed on the cluster piece 1400 and / or the information displayed on the center panel 1500.
[0526] [Manufacturing method]
[0527] The layer constituting the hole transport region, the emission layer and the layer constituting the electron transport region can be formed in a selected region by using various methods (e.g., vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, laser induced thermal imaging, etc.).
[0528] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by vacuum deposition, the deposition temperature may be about 100° C. to about 500° C., about 10 -8 About 10 -3 Torr vacuum and approx. / second to about Deposition was carried out at a deposition rate of / s.
[0529] [Definition of terms]
[0530] As used herein, the term "C 3 -C 60 A "carbocyclic group" may be a cyclic group consisting of carbon atoms as the only ring-forming atoms and having three to sixty carbon atoms (e.g., 3 to 30, 3 to 20, 3 to 15, or 3 to 10 carbon atoms), and the term "C 1 -C 60 The "heterocyclic group" may be a cyclic group having one to sixty carbon atoms (e.g., 1 to 30, 1 to 20, 1 to 15, or 1 to 10 carbon atoms) and further including heteroatoms other than carbon atoms as ring-forming atoms. 3 -C 60 Carbocyclic groups and C 1 -C 60 The heterocyclic groups may each be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are fused to each other. 1 -C 60 The heterocyclic group can have 3 to 61 ring-forming atoms (eg, 3 to 30, 3 to 20, 3 to 15, or 3 to 10 ring-forming atoms).
[0531] As used herein, the term "cyclic group" may be a C 3 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic group.
[0532] As used herein, the term "π-electron-rich C 3 -C 60 The "cyclic group" may be a cyclic group having three to sixty carbon atoms (e.g., 3 to 30, 3 to 20, 3 to 15, or 3 to 10 carbon atoms) and may not contain *-N=*' as a ring-forming part, and the term "π-electron-deficient nitrogen-containing C 1 -C 60The "cyclic group" may be a heterocyclic group having one to sixty carbon atoms (eg, 1 to 30, 1 to 20, 1 to 15, or 1 to 10 carbon atoms) and may contain *-N=*' as a ring-forming portion.
[0533] In an implementation scheme,
[0534] C 3 -C 60 The carbocyclic group may be a T1 group or a group in which two or more T1 groups are fused to each other (e.g., a cyclopentadiene group, an adamantane group, a norbornane group, a phenyl group, a pentalene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a phenanthrenyl group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a benzophenone group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, an indenophenanthrene group or an indenoanthracene group),
[0535] C 1 -C 60The heterocyclic group may be a T2 group, a group in which two or more T2 groups are fused to each other, or a group in which at least one T2 group and at least one T1 group are fused to each other (for example, a pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzisoindole group, a naphthoisoindole group, a benzothiorrole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzothiorrole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolecarbazole group, a benzofuranocarbazole group, a benzothiophenocarbazole group, a benzothiorrolecarbazole group, a benzoindolecarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthosilole group, a benzofuranodibenzofuran group, a benzofuranodibenzothiophene group, a benzo Thienodibenzothiophene group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, oxadiazole group, thiazole group, isothiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzisoxazole group, benzothiazole group, benzisothiazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, etc.),
[0536] Pi-electron-rich C 3 -C 60 The cyclic group may be a T1 group, a group in which two or more T1 groups are fused to each other, a T3 group, a group in which two or more T3 groups are fused to each other, or a group in which at least one T3 group and at least one T1 group are fused to each other (e.g., C 3 -C 60a carbocyclic group, a 1H-pyrrole group, a thiol group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzothiol group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzothiol group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolecarbazole group, a benzofuranocarbazole group, a benzothiophenocarbazole group, a benzothioylcarbazole group, a benzoindolecarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonaphthothiophene group, a benzonaphthothiol group, a benzofuranodibenzofuran group, a benzofuranodibenzothiophene group, a benzothiophenodibenzothiophene group, and the like),
[0537] π-electron-deficient nitrogen-containing C 1 -C 60 The cyclic group may be a T4 group, a group in which two or more T4 groups are fused to each other, a group in which at least one T4 group and at least one T1 group are fused to each other, a group in which at least one T4 group and at least one T3 group are fused to each other, or a group in which at least one T4 group, at least one T1 group and at least one T3 group are fused to each other (e.g., a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzisoxazolyl ... a triazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzoimidazole group, a benzoxazole group, a triazole group, an oxadiazole group, a triazole group, an oxazole group, an isoxazole group, a triazole group, an oxadiazole group, a triazole group, an oxadiazole group, a triazole group, an oxadiazole group, a triazole group, an oxadiazole group, a triazole group, an oxadiazole group, an isoxazole group, a benzopyrazole group, a triazole group, an isoxazole group, a triazole group, an isoxazole group, a triazole group, an isoxazole group, a triazole group, an isoxazole group, a triazole group, an azole group, benzothiazole group, benzisothiazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group, benzoisoquinoline group, quinoxaline group, benzoquinoxaline group, quinazoline group, benzoquinazoline group, phenanthroline group, cinnoline group, phthalazine group, naphthyridine group, imidazopyridine group, imidazopyrimidine group, imidazotriazine group, imidazopyrazine group, imidazopyridazine group, azacarbazole group, azafluorene group, azadibenzosilole group, azadibenzothiophene group, azadibenzofuran group, etc.),
[0538] The T1 group can be a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclobutene group, a cyclopentene group, a cyclopentadiene group, a cyclohexene group, a cyclohexadiene group, a cycloheptene group, an adamantane group, a norbornane (or bicyclo[2.2.1]heptane) group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group or a phenyl group.
[0539] The T2 group can be a furan group, a thiophene group, a 1H-pyrrole group, a thiol group, a borolide group, a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azathiol group, an azaborol group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a tetrazine group, a pyrrolidine group, an imidazolidinyl group, a dihydropyrrole group, a piperidine group, a tetrahydropyridine group, a dihydropyridine group, a hexahydropyrimidine group, a tetrahydropyrimidine group, a dihydropyrimidine group, a piperazine group, a tetrahydropyrazine group, a dihydropyrazine group, a tetrahydropyridazine group or a dihydropyridazine group,
[0540] The T3 group may be a furan group, a thiophene group, a 1H-pyrrole group, a thiole group or a borole group, and
[0541] The T4 group can be a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azathiazole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group or a tetrazine group.
[0542] As used herein, the terms "cyclic group", "C 3 -C 60 Carbocyclic group", "C 1 -C 60 Heterocyclic groups", "π-electron-rich C 3 -C 60 Cyclic group" or "π-electron-deficient nitrogen-containing C 1 -C 60 The “cyclic group” may each be a group condensed with any cyclic group, a monovalent group or a polyvalent group (e.g., a divalent group, a trivalent group, a tetravalent group, etc.) according to the structure of the formula using the corresponding term. In the embodiment, the “phenyl group” may be a benzo group, a phenyl group, a phenylene group, etc., which can be easily understood by a person of ordinary skill in the art based on the structure of the formula including the “phenyl group”.
[0543] In an embodiment, the monovalent C 3 -C 60 Carbocyclic group or monovalent C 1 -C 60 Examples of heterocyclic groups may include C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups and monovalent non-aromatic fused heteropolycyclic groups. 3 -C 60 Carbocyclic group or divalent C 1 -C 60 Examples of heterocyclic groups may include C 3 -C 10 Cycloalkylene group, C 1 -C 10 Heterocycloalkylene group, C 3 -C 10 Cycloalkenylene group, C 1 -C 10 Heterocycloalkenylene group, C 6 -C 60 Arylene group, C 1 -C 60 a heteroarylene group, a divalent non-aromatic fused polycyclic group, and a divalent non-aromatic fused heteropolycyclic group.
[0544] As used herein, the term "C 1 -C 60 The “alkyl group” may be a linear or branched aliphatic hydrocarbon monovalent group having one to sixty carbon atoms (e.g., 1 to 30, 1 to 20, 1 to 15, or 1 to 10 carbon atoms), and examples thereof may include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, and a tert-decyl group. As used herein, the term “C 1 -C 60 The "alkylene group" may be a 1 -C 60 A divalent group of the same structure as an alkyl group.
[0545] As used herein, the term "C 2 -C 60 The "alkenyl group" may be2 -C 60 The term "C" as used herein refers to a monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminal of the alkyl group, and examples thereof may include a vinyl group, a propenyl group, and a butenyl group. 2 -C 60 The "alkenylene group" may be a 2 -C 60 Alkenyl groups are divalent groups of the same structure.
[0546] As used herein, the term "C 2 -C 60 The "alkynyl group" may be in C 2 -C 60 The term "C" as used herein refers to a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the terminal of the alkyl group, and examples thereof may include an ethynyl group and a propynyl group. 2 -C 60 The "alkynylene group" may be a 2 -C 60 Alkynyl groups are divalent groups of the same structure.
[0547] As used herein, the term "C 1 -C 60 The "alkoxy group" may be -O(A 101 )(where A 101 Can be C 1 -C 60 An alkyl group) is a monovalent group, and examples thereof may include a methoxy group, an ethoxy group, and an isopropoxy group.
[0548] As used herein, the term "C 3 -C 10 The term "cycloalkyl group" may be a monovalent saturated hydrocarbon cyclic group having three to ten carbon atoms, and examples thereof may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group (or a bicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, and a bicyclo[2.2.2]octyl group. As used herein, the term "C 3 -C 10 The cycloalkylene group may be a 3 -C 10 Cycloalkyl groups are divalent groups of the same structure.
[0549] As used herein, the term "C 1 -C 10The term "heterocycloalkyl group" as used herein may be a monovalent cyclic group having one to ten carbon atoms and further containing at least one heteroatom other than carbon atoms as a ring-forming atom, and examples thereof may include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothienyl group. 1 -C 10 The "heterocycloalkylene group" may be a 1 -C 10 Heterocycloalkyl groups are divalent groups of the same structure.
[0550] As used herein, the term "C 3 -C 10 The term "cycloalkenyl group" as used herein may be a monovalent cyclic group having three to ten carbon atoms and at least one carbon-carbon double bond in its ring structure and having no aromaticity, and examples thereof may include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. 3 -C 10 The "cycloalkenylene group" may be a 3 -C 10 Cycloalkenyl groups are divalent groups of the same structure.
[0551] As used herein, the term "C 1 -C 10 The "heterocycloalkenyl group" may be a monovalent cyclic group having one to ten carbon atoms in its cyclic structure, further containing at least one heteroatom other than carbon atoms as a ring-forming atom and having at least one double bond. 1 -C 10 Examples of the heterocycloalkenyl group may include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, and a 2,3-dihydrothienyl group. 1 -C 10 The "heterocycloalkenylene group" may be a 1 -C 10 Heterocycloalkenyl groups are divalent groups of the same structure.
[0552] As used herein, the term "C 6 -C 60 An "aryl group" may be a monovalent group having a carbocyclic aromatic system containing six to sixty carbon atoms (e.g., 6 to 30, 6 to 20, 6 to 15, or 6 to 10 carbon atoms), and the term "C 6 -C 60The "arylene group" may be a divalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms (e.g., 6 to 30, 6 to 20, 6 to 15, or 6 to 10 carbon atoms). 6 -C 60 Examples of the aryl group may include a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylene group, a pyrenyl group, The phenyl groups include phenyl groups, peryl groups, pentaphenyl groups, heptaphenyl groups, tetraphenyl groups, naphthacene groups, hexaphenyl groups, pentacene groups, rubidinyl groups, corynyl groups and ovaphenyl groups. 6 -C 60 Aryl groups and C 6 -C 60 When the arylene groups each include two or more rings, two or more corresponding rings may be fused to each other.
[0553] As used herein, the term "C 1 -C 60 The term "heteroaryl group" may be a monovalent group having a heterocyclic aromatic system having one to sixty carbon atoms (e.g., 1 to 30, 1 to 20, 1 to 15, or 1 to 10 carbon atoms) and further containing at least one heteroatom other than a carbon atom as a ring-forming atom. As used herein, the term "C 1 -C 60 The "heteroarylene group" may be a divalent group having a heterocyclic aromatic system having one to sixty carbon atoms (e.g., 1 to 30, 1 to 20, 1 to 15, or 1 to 10 carbon atoms) and further containing at least one heteroatom other than a carbon atom as a ring-forming atom. 1 -C 60 Examples of the heteroaryl group may include a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, a benzoquinolyl group, an isoquinolyl group, a benzoisoquinolyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthrolinyl group, a phthalazinyl group, and a naphthyridinyl group. 1 -C 60 Heteroaryl groups and C 1 -C 60 When the heteroarylene groups each contain two or more rings, the two or more corresponding rings may be fused to each other.
[0554] As used herein, the term "monovalent non-aromatic fused polycyclic group" may be a monovalent group having two or more rings fused to each other, only carbon atoms (e.g., eight to sixty carbon atoms, e.g., 8 to 30, 8 to 20, 8 to 15, or 8 to 10 carbon atoms) as ring atoms, and no aromaticity in its molecular structure when considered as a whole. Examples of monovalent non-aromatic fused polycyclic groups may include indenyl groups, fluorenyl groups, spiro-bifluorenyl groups, benzofluorenyl groups, indenophenanthryl groups, and indenoanthryl groups. As used herein, the term "divalent non-aromatic fused polycyclic group" may be a divalent group having the same structure as the monovalent non-aromatic fused polycyclic group.
[0555] The term “monovalent non-aromatic fused heteropolycyclic group” as used herein may be a monovalent group having two or more rings fused to each other, further containing at least one heteroatom other than carbon atoms (e.g., 1 to 60 carbon atoms, for example, 1 to 30, 1 to 20, 1 to 15, or 1 to 10 carbon atoms) as a ring-constituting atom, and having no aromaticity in its molecular structure when viewed as a whole. Examples of the monovalent non-aromatic condensed heteropolycyclic group may include a pyrrolyl group, a thienyl group, a furanyl group, an indolyl group, a benzindolyl group, a naphthoindolyl group, an isoindolyl group, a benzisoindolyl group, a naphthoisoindolyl group, a benzothiorolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzothiorolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzothiorolyl group, an azadibenzothiophenyl group, an azadibenzofuranyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group The invention also includes but is not limited to: a benzothiazolyl group, a benzopyrazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzoxadiazolyl group, a benzothiadiazolyl group, an imidazopyridyl group, an imidazopyrimidinyl group, an imidazotriazine group, an imidazopyrazinyl group, an imidazopyridazinyl group, an indenocarbazolyl group, an indolecarbazolyl group, a benzofuranocarbazolyl group, a benzothiophenocarbazolyl group, a benzothiorrolocarbazolyl group, a benzoindolecarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophene group, a benzonaphthothiorryl group, a benzofuranodibenzofuranyl group, a benzofuranodibenzothiophene group and a benzothiophenodibenzothiophene group. The term "divalent non-aromatic condensed heteropolycyclic group" as used herein may be a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
[0556] As used herein, the term "C 6 -C60 The "aryloxy group" may be -O(A 102 )(where A 102 Can be C 6 -C 60 aryl group), and as used herein, the term "C 6 -C 60 The "arylthio group" may be -S(A 103 )(where A 103 Can be C 6 -C 60 A group represented by an aryl group.
[0557] As used herein, the term "C 7 -C 60 The "arylalkyl group" may be -(A 104 )(A 105 )(where A 104 Can be C 1 -C 54 An alkylene group, and A 105 Can be C 6 -C 59 aryl group), and as used herein, the term "C 2 -C 60 A "heteroarylalkyl group" may be composed of -(A 106 )(A 107 )(where A 106 Can be C 1 -C 59 An alkylene group, and A 107 Can be C 1 -C 59 A group represented by a heteroaryl group.
[0558] In the specification, the group "R 10a " can be:
[0559] deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group or a nitro group;
[0560] Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 7 -C 60 Arylalkyl group, C2 -C 60 Heteroarylalkyl groups, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof substituted C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group or C 1 -C 60 Alkoxy groups;
[0561] Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 7 -C 60 Arylalkyl group, C 2 -C 60 Heteroarylalkyl groups, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21)(Q 22 ) or any combination thereof substituted C 3 -C 60 Carbocyclic group, C 1 -C 60 Heterocyclic group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 7 -C 60 Arylalkyl group, or C 2 -C 60 a heteroarylalkyl group; or
[0562] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) or -P(=O)(Q 31 )(Q 32 ).
[0563] In the specification, the group Q as used herein 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can each independently be: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; C 1 -C 60 Alkyl group; C 2 -C 60 Alkenyl group; C 2 -C 60 Alkynyl group; C 1 -C 60 alkoxy groups; or each unsubstituted or substituted with deuterium, -F, cyano groups, C 1 -C 60 Alkyl group, C 1 -C 60 C substituted with an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group or any combination thereof 3 -C 60 Carbocyclic group, C 1 -C60 Heterocyclic group, C 7 -C 60 Arylalkyl group, or C 2 -C 60 Heteroarylalkyl groups.
[0564] The term "heteroatom" as used herein may be any atom other than a carbon atom or a hydrogen atom, and the number of the heteroatom may be 1 to 10, for example, 1, 2, 3, 4, or 5. Examples of the heteroatom may include O, S, N, P, Si, B, Ge, Se, or any combination thereof.
[0565] The term “transition metal” as used herein may include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), and gold (Au).
[0566] In the specification, the term "Ph" refers to a phenyl group, the term "Me" refers to a methyl group, the term "Et" refers to an ethyl group, the term "tert-Bu" or "Bu t ” each refers to a tert-butyl group, and the term “OMe” refers to a methoxy group.
[0567] As used herein, the term "biphenyl group" may be a "phenyl group substituted by a phenyl group". For example, a "biphenyl group" may be a 6 -C 60 Aryl groups are substituted phenyl groups as substituents.
[0568] The term "terphenyl group" as used herein may be a "phenyl group substituted by a biphenyl group". For example, a "terphenyl group" is a phenyl group substituted by a C 6 -C 60 Aryl-substituted C 6 -C 60 Aryl groups are substituted phenyl groups as substituents.
[0569] Unless otherwise defined, the symbols * and *' as used herein each refer to a binding site to an adjacent atom in the corresponding formula or moiety.
[0570] In this document, the terms "x-axis", "y-axis", and "z-axis" are not limited to the three axes in a rectangular coordinate system (e.g., a Cartesian coordinate system), and can be interpreted in a broader sense than the aforementioned three axes. For example, the x-axis, y-axis, and z-axis can describe axes that are orthogonal to each other, or can describe axes in different directions that are not orthogonal to each other.
[0571] Hereinafter, the compound according to the embodiment and the light emitting device according to the embodiment will be described in detail with reference to the following synthesis examples and examples. The phrase "using B instead of A" used to describe the synthesis examples means that B is substituted for A with an equimolar equivalent.
[0572] [Synthesis Examples and Examples]
[0573] Synthesis Example 1: Synthesis of Compound 2
[0574]
[0575] Synthesis of intermediate 2-1
[0576] 5 g of 9H-carbazole-1,2,3,4,5,6,7,8-d8 (CAS No. 38537-24-5), 12.39 g of (3-bromophenyl-2,4,5,6-d4)tris(phenyl-d5)silane, 21 g of NaOtBu, 1.04 g of Pd 2 (dba) 3 and 0.51 ml of P(t-Bu) 3 Dissolved in 140 ml of toluene and stirred at 110° C. for 12 hours. After the reaction was completed, the reaction solution was subjected to an extraction process, and the obtained organic layer was dried. After the residue was subjected to purification, 12.37 g (yield: 82%) of Intermediate 2-1 was obtained. Intermediate 2-1 was identified by LC-MS. (C 36 D 27 NSi: M+1 528.87)
[0577] Synthesis of intermediate 2-2
[0578] 12.37 g of intermediate 2-1 was dissolved in 110 ml of DMF and stirred at 0° C. for 30 minutes. 4.16 g of NBS was slowly added at 0° C., and after 1 hour, the mixed solution was stirred at room temperature for 6 hours. After the reaction was completed, the reaction solution was subjected to an extraction process, and the obtained organic layer was dried. After the residue was subjected to purification, 13.77 g (yield: 97%) of intermediate 2-2 was obtained. Intermediate 2-2 was identified by LC-MS. (C 36 D 26 BrNSi:M+1 606.76)
[0579] Synthesis of intermediate 2-3
[0580] 13.77 g of intermediate 2-2, 5.76 g of bis(pinacolato)diboron, 6.68 g of KOAc and 0.79 g of Pd(dppf)Cl 2Dissolved in 110 ml of 1,4-dioxane, and then stirred at 120° C. for 12 hours. After the reaction was completed, the reaction solution was subjected to an extraction process, and the obtained organic layer was dried. After the residue was subjected to purification, 11.87 g (yield: 80%) of Intermediate 2-3 was obtained. Intermediate 2-3 was identified by LC-MS. (C 42 H 12 D 26 BNO 2 Si: M+1 653.82)
[0581] Synthesis of intermediate 2-4
[0582] 11.87 g of intermediate 2-3, 2.88 g of 1-bromo-3-iodobenzene-2,4,5,6-d4 (CAS No. 2363787-31-7), 28.34 ml of 2M K 2 CO 3 aqueous solution and 1.31 g of Pd(PPh 3 ) 4 Dissolved in 100 ml of THF solvent and stirred at 80° C. for 12 hours. After the reaction was completed, the reaction solution was subjected to an extraction process, and the obtained organic layer was dried. After the residue was subjected to purification, 13.24 g (yield: 85%) of Intermediate 2-4 was obtained. Intermediate 2-4 was identified by LC-MS. (C 42 D 30 BrNSi:M+1 686.88)
[0583] Synthesis of intermediate 2-5
[0584] 13.24 g of intermediate 2-4, 4.89 g of bis(pinacolato)diboron, 5.68 g of KOAc and 0.68 g of Pd(dppf)Cl 2 Dissolved in 100 ml of 1,4-dioxane and stirred at 120° C. for 12 hours. After the reaction was completed, the reaction solution was subjected to an extraction process, and the obtained organic layer was dried. After the residue was subjected to purification, 10 g (yield: 80%) of Intermediate 2-5 was obtained. Intermediate 2-5 was identified by LC-MS. (C 48 H 12 D 30 BNO 2 Si: M+1 733.95)
[0585] Synthesis of intermediate 2-6
[0586] 10 g of 9H-carbazole-1,2,3,4,5,6,7,8-d8 (CAS No. 38537-24-5), 8.96 g of bromobenzene, 10.97 g of NaOtBu, 2.09 g of Pd 2 (dba) 3 and 1.03 ml of P(t-Bu) 3 Dissolved in 280 ml of toluene and stirred at 110° C. for 12 hours. After the reaction was completed, the reaction solution was subjected to an extraction process, and the obtained organic layer was dried. After the residue was subjected to purification, 12.19 g (yield: 85%) of Intermediate 2-6 was obtained. Intermediate 2-6 was identified by LC-MS. (C 18 H 5 D 8 N: M+1 251.36)
[0587] Synthesis of intermediate 2-7
[0588] 12.19 g of intermediate 2-6 was dissolved in 240 ml of DMF and stirred at 0° C. for 30 minutes. 8.63 g of NBS was slowly added, and after 1 hour, the mixed solution was stirred at room temperature for 6 hours. After the reaction was completed, the reaction solution was subjected to an extraction process, and the obtained organic layer was dried. After the residue was subjected to purification, 28.5 g (yield: 97%) of intermediate 2-7 was obtained. Intermediate 2-7 was identified by LC-MS. (C 18 H 5 D 7 BrN:M+1329.25)
[0589] Synthesis of compound 2
[0590] 2 g of intermediate 2-7, 4.45 g of intermediate 2-5, 7.6 ml of 2M K 2 CO 3 aqueous solution and 0.35 g of Pd(PPh 3 ) 4 Dissolved in 28 ml of THF solvent, and then stirred at 80° C. for 12 hours. After the reaction was completed, the reaction solution was subjected to an extraction process, and the obtained organic layer was dried. The residue was separated and purified by column chromatography, followed by recrystallization and sublimation purification to obtain 3.55 g (yield: 85%) of high-purity compound 2. By LC-MS and 1 Compound 2 was identified by H-NMR.
[0591] Synthesis Example 2: Synthesis of Compound 4
[0592]
[0593]
[0594] Synthesis of intermediate 4-1
[0595] 5 g of 9H-carbazole-1,2,3,4,5,6,7,8-d8 (CAS No. 38537-24-5), 6.79 g of 3-bromo-1,1'-biphenyl-2',3',4',5',6'-d5 (CAS No. 51624-39-6), 5.48 g of NaOtBu, 1.04 g of Pd 2 (dba) 3 and 0.51 ml of P(t-Bu) 3 Dissolved in 140 ml of toluene and stirred at 110° C. for 12 hours. After the reaction was completed, the reaction solution was subjected to an extraction process, and the obtained organic layer was dried. After the residue was subjected to purification, 8.06 g (yield: 85%) of Intermediate 4-1 was obtained. Intermediate 4-1 was identified by LC-MS. (C 24 H 4 D 13 N: M+1332.49)
[0596] Synthesis of intermediate 4-2
[0597] 8.06 g of intermediate 4-1 was dissolved in 120 ml of DMF and stirred at 0° C. for 30 minutes. 4.31 g of NBS was slowly added, and after 1 hour, stirred at room temperature for 6 hours. After the reaction was completed, the reaction solution was extracted, and the obtained organic layer was dried. After the residue was purified, 9.65 g (yield: 97%) of intermediate 4-2 was obtained. Intermediate 4-2 was identified by LC-MS. (C 24 H 4 D 12 BrN: M+1 410.38)
[0598] Synthesis of compound 4
[0599] 2 g of intermediate 4-2, 3.58 g of intermediate 2-5, 6.09 ml of 2M K 2 CO 3 aqueous solution and 0.28 g of Pd(PPh 3 ) 4 Dissolved in 24 ml of THF solvent and stirred at 80° C. for 12 hours. After the reaction was completed, the reaction solution was subjected to an extraction process, and the obtained organic layer was dried. The residue was separated and purified by column chromatography, followed by recrystallization and sublimation purification to obtain 2.85 g (yield: 85%) of high-purity compound 4. By LC-MS and 1 Compound 4 was identified by H-NMR.
[0600] Synthesis Example 3: Synthesis of Compound 6
[0601]
[0602] Synthesis of intermediate 6-1
[0603] 5 g of 9H-carbazole-1,2,3,4,5,6,7,8-d8 (CAS No. 38537-24-5), 6.79 g of 4-bromo-1,1'-biphenyl-2',3',4',5',6'-d5 (CAS No. 51624-40-9), 5.48 g of NaOtBu, 1.04 g of Pd 2 (dba) 3 and 0.51 ml of P(t-Bu) 3 Dissolved in 140 ml of toluene and stirred at 110° C. for 12 hours. After the reaction was completed, the reaction solution was subjected to an extraction process, and the obtained organic layer was dried. After the residue was subjected to purification, 8.06 g (yield: 85%) of Intermediate 6-1 was obtained. Intermediate 6-1 was identified by LC-MS. (C 24 H 4 D 13 N: M+1332.49)
[0604] Synthesis of intermediate 6-2
[0605] 8.06 g of intermediate 6-1 was dissolved in 120 ml of DMF and stirred at 0° C. for 30 minutes. 4.31 g of NBS was slowly added, and after 1 hour, the mixed solution was stirred at room temperature for 6 hours. After the reaction was completed, the reaction solution was subjected to an extraction process, and the obtained organic layer was dried. After the residue was subjected to purification, 9.65 g (yield: 97%) of intermediate 6-2 was obtained. Intermediate 6-2 was identified by LC-MS. (C 24 H 4 D 12 BrN: M+1 410.38)
[0606] Synthesis of compound 6
[0607] 2 g of intermediate 6-2, 3.58 g of intermediate 2-5, 6.09 ml of 2M K 2 CO 3 aqueous solution and 0.28 g of Pd(PPh 3 ) 4Dissolved in 24 ml of THF solvent and stirred at 80° C. for 12 hours. After the reaction was completed, the reaction solution was subjected to an extraction process, and the obtained organic layer was dried. The residue was separated and purified by column chromatography, followed by recrystallization and sublimation purification to obtain 3.97 g (yield: 87%) of high-purity compound 6. By LC-MS and 1 Compound 6 was identified by H-NMR.
[0608] Synthesis Example 4: Synthesis of Compound 18
[0609]
[0610] Synthesis of intermediate 18-1
[0611] 5 g of 9H-carbazole-1,2,3,4,5,6,7,8-d8 (CAS No. 38537-24-5), 10.83 g of 1,3-dibromo-2-fluorobenzene and 12.11 g of K 3 PO 4 Dissolved in 140 ml of DMF and stirred at 160° C. for 12 hours. After the reaction was completed, the reaction solution was extracted and the obtained organic layer was dried. After the residue was subjected to purification, 9.92 g (yield: 85%) of Intermediate 18-1 was obtained. Intermediate 18-1 was identified by LC-MS. (C 18 H 3 D 8 Br 2 N: M+1 409.15)
[0612] Synthesis of intermediate 18-2
[0613] 9.92 g of intermediate 18-1, 35.48 g of (phenyl-d5) boronic acid (CAS No. 215527-70-1), 48 ml of 2MK 2 CO 3 aqueous solution and 1.39 g of Pd(PPh 3 ) 4 Dissolved in 120 ml of THF solvent and stirred at 80° C. for 12 hours. After the reaction was completed, the reaction solution was subjected to an extraction process, and the obtained organic layer was dried. After the residue was subjected to purification, 7.59 g (yield: 76%) of Intermediate 18-2 was obtained. Intermediate 18-2 was identified by LC-MS. (C 30 H 3 D 18 N: M+1 413.61)
[0614] Synthesis of intermediate 18-3
[0615] 7.59 g of intermediate 18-2 was dissolved in 110 ml of DMF and stirred at 0° C. for 30 minutes. 4.06 g of NBS was slowly added, and after 1 hour, the mixed solution was stirred at room temperature for 6 hours. After the reaction was completed, the reaction solution was subjected to an extraction process, and the obtained organic layer was dried. After the residue was subjected to purification, 9.08 g (yield: 97%) of intermediate 18-3 was obtained. Intermediate 18-3 was identified by LC-MS. (C 30 H 3 D 17 BrN: M+1 491.50)
[0616] Synthesis of compound 18
[0617] 2 g of intermediate 18-3, 2.98 g of intermediate 2-5, 5.08 ml of 2M K 2 CO 3 aqueous solution and 0.24 g of Pd(PPh 3 ) 4 Dissolved in 20 ml of THF solvent and stirred at 80° C. for 12 hours. After the reaction was completed, the reaction solution was subjected to an extraction process, and the obtained organic layer was dried. The residue was separated and purified by column chromatography, followed by recrystallization and sublimation purification to obtain 3.56 g (yield: 86%) of high-purity compound 18. By LC-MS and 1 Compound 18 was identified by H-NMR.
[0618] Synthesis Example 5: Synthesis of Compound 22
[0619]
[0620]
[0621] Synthesis of Intermediate 22-1
[0622] 10 g of intermediate 2-3, 4.39 g of 1-bromo-2-iodobenzene-2,4,5,6-d4, 19 ml of 2M K 2 CO 3 aqueous solution and 0.88 g of Pd(PPh 3 ) 4 Dissolved in 75 ml of THF solvent and stirred at 80° C. for 12 hours. After the reaction was completed, the reaction solution was subjected to an extraction process, and the obtained organic layer was dried. After the residue was subjected to purification, 9.03 g (yield: 86%) of Intermediate 22-1 was obtained. Intermediate 22-1 was identified by LC-MS. (C 42 D 30 BrNSi: M+1 686.88)
[0623] Synthesis of intermediate 22-2
[0624] 9.03 g of intermediate 22-1, 3.34 g of bis(pinacolato)diboron, 3.87 g of KOAc and 0.46 g of Pd(dppf)Cl 2 Dissolved in 65 ml of 1,4-dioxane and stirred at 120° C. for 12 hours. After the reaction was completed, the reaction solution was subjected to an extraction process, and the obtained organic layer was dried. After the residue was subjected to purification, 7.72 g (yield: 80%) of Intermediate 22-2 was obtained. Intermediate 22-2 was identified by LC-MS. (C 48 H 12 D 30 BNO 2 Si: M+1733.95)
[0625] Synthesis of compound 22
[0626] 2 g of intermediate 22-2, 0.9 g of intermediate 2-7, 3.41 ml of 2M K 2 CO 3 aqueous solution and 0.16 g of Pd(PPh 3 ) 4 Dissolved in 13 ml of THF solvent and stirred at 80° C. for 12 hours. After the reaction was completed, the reaction solution was subjected to an extraction process, and the obtained organic layer was dried. The residue was separated and purified by column chromatography, followed by recrystallization and sublimation purification to obtain 2 g (yield: 86%) of high-purity compound 22. By LC-MS and 1 Compound 22 was identified by H-NMR.
[0627] Synthesis Example 6: Synthesis of Compound 24
[0628]
[0629] Synthesis of compound 24
[0630] 2 g of intermediate 22-2, 1.12 g of intermediate 4-2, 3.4 ml of 2M K 2 CO 3 aqueous solution and 0.16 g of Pd(PPh 3 ) 4 Dissolved in 13 ml of THF solvent and stirred at 80° C. for 12 hours. After the reaction was completed, the reaction solution was subjected to an extraction process, and the obtained organic layer was dried. The residue was separated and purified by column chromatography, followed by recrystallization and sublimation purification to obtain 2.17 g (yield: 85%) of high-purity compound 24. By LC-MS and 1Compound 24 was identified by H-NMR.
[0631] Synthesis Example 7: Synthesis of Compound 26
[0632]
[0633] Synthesis of compound 26
[0634] 2 g of intermediate 22-2, 1.12 g of intermediate 6-2, 3.41 ml of 2M K 2 CO 3 aqueous solution and 0.16 g of Pd(PPh 3 ) 4 Dissolved in 13 ml of THF solvent and stirred at 80° C. for 12 hours. After the reaction was completed, the reaction solution was subjected to an extraction process, and the obtained organic layer was dried. The residue was separated and purified by column chromatography, followed by recrystallization and sublimation purification to obtain 2.12 g (yield: 83%) of high-purity compound 26. By LC-MS and 1 Compound 26 was identified by H-NMR.
[0635] [Table 1]
[0636]
[0637] Example 1
[0638] As the anode, 15Ω / cm 2 An ITO glass substrate (purchased from Corning Co., Ltd) was cut into a size of 50 mm×50 mm×0.5 mm, ultrasonically treated in isopropanol and pure water for 5 minutes in each solvent, and cleaned by ultraviolet irradiation and exposure to ozone for 30 minutes, and the glass substrate was loaded onto a vacuum deposition apparatus.
[0639] HAT-CN is deposited on a substrate to form a A hole injection layer with a thickness of 1000 Å was formed, and BCFN (HT3) as a first hole transport material was vacuum deposited thereon to a thickness of 1000 Å. and vacuum depositing SiCzCz (HT47) as a hole transport material of a second hole transport compound onto The thickness of the film is 2000 nm, thereby forming a hole transport layer.
[0640] Compound 2 and SiTrzCz2 (H129) as hosts and PtON-TBBI (PD38) as phosphorescent dopant were co-deposited on the hole transport layer in a weight ratio of 60:27:13 to form a The thickness of the emission layer.
[0641] mSiTrz (ET46) is deposited on the emission layer to form a A first electron transport layer having a thickness of , and mSiTrz (ET46) and Liq are co-deposited thereon in a weight ratio of 1:1 to form a A second electron transport layer having a thickness of 1000 nm is formed, thereby forming an electron transport layer. LiF as an alkali metal halide is deposited on the electron transport layer to form a An electron injection layer of thickness of 1000 mm was formed, and Al was vacuum deposited thereon to A thickness of is achieved, thereby forming a LiF / Al electrode, and thus completing the manufacture of the light-emitting device.
[0642]
[0643] Examples 2 to 7 and Comparative Examples 1 to 5
[0644] Light-emitting devices were manufactured in the same manner as in Example 1, except that the compounds shown in Table 2 were used instead of Compound 2 to form the emission layer.
[0645] Evaluation Example 1
[0646] In order to evaluate the characteristics of the light-emitting devices manufactured in the examples and comparative examples, the current at 10 mA / cm 2 The driving voltage, current density and maximum quantum efficiency under the current density of . The driving voltage and current density of the light-emitting device are measured by using a source meter (Keithley Instrument, 2400 series), and the maximum quantum efficiency is measured using the external quantum efficiency measurement device C9920-2-12 of Hamamatsu Photonics Inc. In evaluating the maximum quantum efficiency, the brightness / current density is measured by using a luminance meter with calibrated wavelength sensitivity, and the maximum quantum efficiency is converted by assuming that the angular brightness distribution (Lambertian) of a completely reflecting diffuser is introduced. In the case of relative service life, the time taken for the brightness to reach 95% of the initial brightness is measured, and the relative service life is represented by setting the device service life of Comparative Example 1 to 100%. The triplet energy level (T 1 ). Table 2 shows the evaluation results of the characteristics of the organic light-emitting device.
[0647] [Table 2]
[0648]
[0649]
[0650]
[0651] It can be confirmed from Table 2 that the light-emitting devices according to Examples 1 to 7 are superior to the light-emitting devices according to Comparative Examples 1 to 5 in terms of driving voltage, maximum quantum efficiency, relative device life, triplet energy level (T 1 ) and color purity.
[0652] By including the heterocyclic compound represented by Chemical Formula 1, the light emitting device according to the embodiment may have excellent driving voltage, excellent maximum quantum efficiency characteristics, excellent lifespan characteristics, and excellent triplet energy level characteristics, and high-quality electronic devices and high-quality electronic devices may be manufactured by using the light emitting device.
[0653] Embodiments have been disclosed herein, and although terms are used, they are used and interpreted in a general and descriptive sense only and not for purposes of limitation. In some cases, as will be apparent to one of ordinary skill in the art, features, characteristics and / or elements described with respect to an embodiment may be used alone or in combination with features, characteristics and / or elements described with respect to other embodiments, unless specifically noted otherwise. Therefore, one of ordinary skill in the art will appreciate that various changes in form and detail may be made without departing from the spirit and scope of the present disclosure.
Claims
1. A light-emitting device, comprising: a first electrode; a second electrode facing the first electrode; an intermediate layer between the first electrode and the second electrode and including an emission layer; as well as A heterocyclic compound represented by Formula 1: [Formula 1] [Formula 2] In Formula 1 and Formula 2, X1 is C, Si, Ge or Sn, R 11 , R 12 , R 13 , R2, R3, R 41 To R 45 and R 51 To R 53 Each is independently a group represented by Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Aryloxy groups, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 an arylthio group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), but R 41 , R 42 , R 44 and R 45 At least one of them is independently a group represented by Formula 2, and R 43 is not a group represented by formula 2, n2 is an integer from 0 to 4, n3 is an integer from 0 to 7, n51 is an integer from 0 to 5, n52 and n53 are each independently an integer from 0 to 20, Ring CY1 and ring CY2 are each independently C5-C 60 Carbocyclic group or C1-C 60 Heterocyclic group, * indicates the binding site with the adjacent atom, R 10a yes: deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group or a nitro group; Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, C2-C 60 Heteroarylalkyl groups, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 )、-P(=O)(Q 11 )(Q 12 ) or a combination thereof substituted with C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group or C1-C 60 Alkoxy groups; Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group, C1-C 60 Alkoxy groups, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, C2-C 60 Heteroarylalkyl groups, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or a combination thereof substituted C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, or C2-C 60 a heteroarylalkyl group; or -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), and Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are independently: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; C1-C 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 Alkynyl group; C1-C 60 alkoxy groups; each of which is unsubstituted or substituted with deuterium, -F, cyano groups, C1-C 60 Alkyl groups, C1-C 60 C3-C4 substituted with an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group or a combination thereof 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C7-C 60 Arylalkyl group, or C2-C 60 Heteroarylalkyl groups. The light-emitting device of claim 1 , wherein the emission layer comprises the heterocyclic compound.
3. The light emitting device according to claim 1, wherein The emitting layer includes a body, and The host includes the heterocyclic compound. The light emitting device of claim 1 , wherein the emission layer further comprises an emitter, a sensitizer, or a combination thereof. The light emitting device of claim 1 , wherein the emission layer further comprises a phosphorescent compound, a fluorescent compound, or a combination thereof. The light emitting device of claim 1 , wherein the emitting layer emits blue light.
7. An electronic device comprising the light emitting device according to any one of claims 1 to 6.
8. The electronic device of claim 7, further comprising a color filter, a color conversion layer, a touch screen layer, a polarization layer, or a combination thereof.
9. An electronic device comprising the light emitting device according to any one of claims 1 to 6.
10. The electronic device of claim 9, wherein the electronic device is a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, an indoor light, an outdoor light, a signal light, a head-up display, a fully transparent display, a partially transparent display, a flexible display, a rollable display, a foldable display, a retractable display, a laser printer, a phone, a mobile phone, a tablet personal computer, a tablet phone, a personal digital assistant, a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay, a three-dimensional display, a virtual reality display, an augmented reality display, a vehicle, a video wall with multiple displays stitched together, a theater screen, a stadium screen, a light therapy device, or a sign.
11. A heterocyclic compound represented by Formula 1: [Formula 1] [Formula 2] In Formula 1 and Formula 2, X1 is C, Si, Ge or Sn, R 11 , R 12 , R 13 , R2, R3, R 41 To R 45 and R 51 To R 53 Each is independently a group represented by Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Alkyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl groups, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl groups, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy groups, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Aryloxy groups, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 an arylthio group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), but R 41 , R 42 , R 44 and R 45 At least one of them is independently a group represented by Formula 2, and R 43 is not a group represented by formula 2, n2 is an integer from 0 to 4, n3 is an integer from 0 to 7, n51 is an integer from 0 to 5, n52 and n53 are each independently an integer from 0 to 20, Ring CY1 and ring CY2 are each independently C5-C 60 Carbocyclic group or C1-C 60 Heterocyclic group, * indicates the binding site with the adjacent atom, R 10a yes: deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group or a nitro group; Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, C2-C 60 Heteroarylalkyl groups, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 )、-P(=O)(Q 11 )(Q 12 ) or a combination thereof substituted with C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group or C1-C 60 Alkoxy groups; Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group, C1-C 60 Alkoxy groups, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, C2-C 60 Heteroarylalkyl groups, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or a combination thereof substituted C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C7-C 60 Arylalkyl group, or C2-C 60 a heteroarylalkyl group; or -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ), and Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are independently: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; C1-C 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 Alkynyl group; C1-C 60 alkoxy groups; each of which is unsubstituted or substituted with deuterium, -F, cyano groups, C1-C 60 Alkyl groups, C1-C 60 C3-C4 substituted with an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group or a combination thereof 60 Carbocyclic groups, C1-C 60 Heterocyclic group, C7-C 60 Arylalkyl group, or C2-C 60 Heteroarylalkyl groups.
12. The heterocyclic compound according to claim 11, wherein ring CY1 and ring CY2 are each independently a benzene group, a naphthyl group or a phenanthrene group.
13. The heterocyclic compound according to claim 11, wherein R 11 , R 12 , R 13 , R2, R3, R 41 To R 45 and R 51 To R 53 Each independently is: A group represented by Formula 2, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a C1-C 20 Alkyl group or C1-C 20 Alkoxy groups; Each of the following is deuterated, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C 10 C1-C12 substituted with an alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridyl group or a pyrimidinyl group. 20 Alkyl group or C1-C 20 Alkoxy groups; Each is unsubstituted or substituted with deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C 20 Alkyl groups, C1-C 20 an alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a 1,2,3,4-tetrahydronaphthyl group, a phenyl group, a biphenyl group, a terphenyl group, a (C1-C 10 alkyl)phenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a pyrrolyl group, a thienyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group group, a carbazolyl group, a phenanthroline group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzisothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazine group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidinyl group, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 )-substituted cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, 1,2,3,4-tetrahydronaphthyl group, phenyl group, biphenyl group, terphenyl group, (C1-C 10 alkyl)phenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a pyrrolyl group, a thienyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group , a benzofuranyl group, a benzothienyl group, a benzisothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothienyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothienyl group, an azafluorenyl group, or an azadibenzosilyl group; or -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), but R 41 , R 42 , R 44 and R 45 At least one of them is independently a group represented by Formula 2, and R 43 is not a group represented by formula 2, Q1 to Q3 and Q 31 To Q 33 Each independently is: -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H or -CD2CDH2; or Each unsubstituted or deuterated, C1-C 10 An n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group, naphthyl group, pyridyl group, pyrimidinyl group, pyridazinyl group, pyrazinyl group or triazinyl group substituted with an alkyl group, a phenyl group, a biphenyl group, a tert-biphenyl group, a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group or a triazinyl group.
14. The heterocyclic compound according to claim 11, wherein R 51 is a group represented by one of Formula 5-1 to Formula 5-19: Wherein in Formula 5-1 to Formula 5-19, z3 is an integer from 0 to 3, z4 is an integer from 0 to 4, z5 is an integer from 0 to 5, z7 is an integer from 0 to 7, and R 10a As defined in Equation 1 and Equation 2, *Indicates the binding site with the adjacent atom.
15. The heterocyclic compound according to claim 11, wherein the group represented by Formula 2 is a group represented by one of Formulas 2-1 to 2-8: In Formula 2-1 to Formula 2-8, R 51 and n51 are each the same as defined in Formula 2, R 52a , R 52b , R 52c , R 52d , R 52e and R 52f Each independently and with respect to R in Formula 2 52 The same definition, R 53a , R 53b , R 53c and R 53d Each independently and with respect to R in Formula 2 53 The same definitions, and *Indicates the binding site with the adjacent atom.
16. The heterocyclic compound according to claim 11, wherein the heterocyclic compound is represented by one of Formula 1-1 to Formula 1-4: [Formula 1-1] [Formula 1-2] [Formula 1-3] [Formula 1-4] In Formula 1-1 to Formula 1-4, X1, R 11 To R 13 and R 41 To R 45 Each is the same as defined in Formula 1, R 21 To R 24 are each independently the same as defined with respect to R2 in Formula 1, and R 31 To R 38 are each independently the same as defined with respect to R3 in Formula 1.
17. The heterocyclic compound of claim 11, wherein the heterocyclic compound comprises at least one deuterium.
18. The heterocyclic compound of claim 11, wherein the heterocyclic compound has a deuterium substitution rate greater than or equal to 9.5%. 19 . The heterocyclic compound according to claim 11 , wherein the heterocyclic compound has a triplet energy level of 2.75 eV to 3.10 eV.
20. The heterocyclic compound according to claim 11, wherein the heterocyclic compound is one of Compound 1 to Compound 40:
Citation Information
Patent Citations
Control device and control method to reduce the output voltage deviation of active clamp converter
KR1020230139857A