Condensed ring compound and organic light-emitting device comprising the same

Abstract

Disclosed are condensed ring compounds and organic light-emitting devices comprising the same. The condensed ring compound is represented by Formula 1, wherein in Formula 1, A1, D1, and R 11 ‑R 14 Same as described in the manual. Formula 1#imgabs0#

Description

[0001] Cross-reference to related applications

[0002] This application claims priority from Korean Patent Application No. 10-2018-0073457 filed on June 26, 2018, and Korean Patent Application No. 10-2018-0150081 filed on November 28, 2018, in the Korean Intellectual Property Office, and all rights arising therefrom, the contents of which are incorporated herein by reference in their entirety. Technical Field

[0003] One or more embodiments relate to a fused ring compound and an organic light-emitting device including the same. Background Art

[0004] Organic light emitting devices (OLEDs) are self-emitting devices that produce full-color images and also have wide viewing angles, high contrast, short response times, and excellent characteristics in terms of brightness, driving voltage, and response speed compared to other types of devices.

[0005] In an embodiment, an organic light-emitting device includes an anode, a cathode, and an organic layer disposed between the anode and the cathode and including an emissive layer. A hole transport region may be disposed between the anode and the emissive layer, and an electron transport region may be disposed between the emissive layer and the cathode. Holes provided from the anode may move toward the emissive layer through the hole transport region, and electrons provided from the cathode may move toward the emissive layer through the electron transport region. Carriers such as holes and electrons recombine in the emissive layer to generate excitons. These excitons transition from an excited state to a ground state, thereby generating light.

[0006] Various types of organic light emitting devices are known. However, there is still a need for OLEDs with low driving voltage, high efficiency, high brightness, and long lifetime. Summary of the Invention

[0007] Aspects of the present disclosure provide a fused ring compound having excellent delayed fluorescence emission characteristics and an organic light emitting device including the same and thus having high efficiency and / or long lifespan.

[0008] Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments.

[0009] One aspect provides a fused ring compound represented by Formula 1:

[0010] Formula 1

[0011]

[0012] Formula 2

[0013]

[0014]

[0015]

[0016] In Formulas 1, 2, and 3-1 to 3-5,

[0017] D1 may be a group represented by Formula 2,

[0018] A1 may be a group represented by one selected from Formulae 3-1 to 3-5,

[0019] R 11 and R 12 Can be each independently substituted or unsubstituted C6-C 30 Aryl,

[0020] A 21 and A 22 and benzothiophene groups,

[0021] X 31 Can be N or C(R 31 );X 32 Can be N or C(R 32 );X 33 Can be N or C(R 33 );X 34 Can be N or C(R 34 );X 35 Can be N or C(R 35 );X 36 Can be N or C(R 36 );X 37 Can be N or C(R 37 ); and X 38 Can be N or C(R 38 ), wherein X is selected from Formula 3-1 31 -X 35 At least one of may be N and is selected from X in formulas 3-2 to 3-5 36 -X 38 At least one of may be N,

[0022] Y 31 Can be selected from O and S,

[0023] R 13 、R 14 、R 21 、R 22 , and R 31 -R 39 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C7-C 60 Arylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryloxy, substituted or unsubstituted C1-C 60 Heteroarylthio, substituted or unsubstituted C2-C 60 heteroarylalkyl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q1)(Q2)(Q3), -N(Q4)(Q5), and -B(Q6)(Q7),

[0024] Selected from R 31 -R 39 Two adjacent groups of may optionally be linked to form a fused ring,

[0025] b21 and b22 may each be independently selected from 1, 2, 3, 4, 5, 6, 7, and 8,

[0026] b39 can be selected from 1, 2, 3, and 4,

[0027] Q1-Q7 can be independently selected from hydrogen, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C1-C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups, and

[0028] * indicates the binding site with the adjacent atom.

[0029] Another aspect provides an organic light emitting device comprising:

[0030] a first electrode;

[0031] a second electrode; and

[0032] an organic layer disposed between the first electrode and the second electrode,

[0033] wherein the organic layer includes an emission layer, and

[0034] The organic layer includes at least one of the fused ring compounds described above. BRIEF DESCRIPTION OF THE DRAWINGS

[0035] By combining Figure 1 These and / or other aspects will become clearer and more readily understood from the following description of the embodiments considered. Figure 1 is a schematic diagram of an organic light-emitting device according to an embodiment. DETAILED DESCRIPTION

[0036] Embodiments will now be described in detail, examples of which are illustrated in the accompanying drawings, wherein similar reference numerals refer to similar elements throughout. In this regard, the present embodiment may have different forms and should not be construed as being limited to the description set forth herein. Therefore, the following description of the embodiments is merely by reference to the accompanying drawings to illustrate aspects of the present disclosure. As used herein, the term "and / or" includes any and all combinations of one or more of the relevant enumerated items. Expressions such as "at least one (kind)" when preceding or following a list of elements modify the entire list of elements without modifying the individual elements of the list.

[0037] It will be understood that when an element is referred to as being “on” another element, it can be in direct contact with the other element or intervening elements may exist therebetween. In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements.

[0038] It will be understood that although the terms first, second, third, etc. may be used in this article to describe various elements, components, regions, layers and / or parts, these elements, components, regions, layers and / or parts should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer or part from another element, component, region, layer or part. Therefore, without departing from the teachings of the present embodiment, the first element, component, region, layer or part discussed below may be referred to as the second element, component, region, layer or part.

[0039] The terms used herein are for the purpose of describing specific embodiments only and are not intended to be limiting. As used herein, the singular forms "a", "an" and "the" are also intended to include the plural forms, unless the context clearly indicates otherwise.

[0040] The term "or" means "and / or". It will be further understood that the terms "include" or "comprising" when used in this specification indicate the presence of stated features, regions, integers, steps, operations, elements, and / or components, but do not preclude the presence or addition of one or more additional features, regions, integers, steps, operations, elements, components, and / or combinations thereof.

[0041] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept belongs. It will 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 the present disclosure, and will not be interpreted in an idealized or overly formal sense unless clearly defined as such herein.

[0042] Exemplary embodiments are described herein with reference to cross-sectional views that are schematic representations of idealized embodiments. As such, deviations from the shapes of the figures are to be expected as a result of, for example, manufacturing techniques and / or tolerances. Thus, the embodiments described herein should not be construed as limited to the specific shapes of the regions as shown herein, but rather include deviations in shape resulting from, for example, manufacturing. For example, a region illustrated or described as flat may typically have rough and / or nonlinear features. Furthermore, sharp corners illustrated may be rounded. Thus, the regions illustrated in the figures are schematic in nature, and their shapes are not intended to illustrate the precise shape of the regions and are not intended to limit the scope of the claims.

[0043] As used herein, "about" or "approximately" is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art taking into account the measurements in question and the errors associated with the measurement of the particular quantity (i.e., the limitations of the measurement system). For example, "about" can mean within one or more ranges of deviation, or within ±10% or 5%, relative to the stated value.

[0044] One aspect of the present disclosure provides a fused ring compound represented by Formula 1, wherein D1 in Formula 1 may be a group represented by Formula 2, and A1 in Formula 1 may be a group represented by one selected from Formulas 3-1 to 3-5:

[0045] Formula 1

[0046]

[0047] Formula 2

[0048]

[0049]

[0050]

[0051] Formulas 1, 2, and 3-1 to 3-5 will be described below.

[0052] R in Formula 1 11 and R 12 Can be independently substituted or unsubstituted C6-C 30 Aryl.

[0053] In one embodiment, R in Formula 1 11 and R 12 Can be independently selected from:

[0054] Phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, anthracenyl, benzo[9,10]phenanthrenyl, pyrenyl, and base; and

[0055] Each of at least one substituted phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, anthracenyl, benzo[9,10]phenanthrenyl, pyrenyl, and Group: deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl, C1-C 20 an alkoxy group, and a phenyl group, but the embodiments of the present disclosure are not limited thereto.

[0056] In one or more embodiments, R in Formula 1 11 and R 12 Can be independently selected from:

[0057] phenyl, biphenyl, terphenyl, and naphthyl; and

[0058] phenyl, biphenyl, terphenyl, and naphthyl, each of which is selected from at least one substituted group selected from the group consisting of deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, and phenyl, but embodiments of the present disclosure are not limited thereto.

[0059] In one or more embodiments, R in Formula 1 11 and R 12 Can be independently selected from:

[0060] phenyl; and

[0061] A phenyl group substituted with at least one selected from the group consisting of a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, and a phenyl group, but embodiments of the present disclosure are not limited thereto.

[0062] A in Formula 2 21 and A 22 Each of the benzofuran and dibenzothiophene groups may be independently selected from a phenyl group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, an indolofluorene group, an indolocarbazole group, an indolodibenzofuran group, an indolodibenzothiophene group, an indenofluorene group, an indenocarbazole group, an indenodibenzofuran group, an indenodibenzothiophene group, a benzofuranofluorene group, a benzofuranocarbazole group, a benzofuranodibenzofuran group, a benzofuranodibenzothiophene group, a benzothienofluorene group, a benzothienocarbazole group, a benzothienodibenzofuran group, and a benzothienodibenzothiophene group.

[0063] In one embodiment, in Formula 2,

[0064] A 21 It can be a phenyl group,

[0065] A 22 It may be selected from a phenyl group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, an indolefluorene group, an indolecarbazole group, an indoledibenzofuran group, an indoledibenzothiophene group, an indenofluorene group, an indenocarbazole group, an indenodibenzofuran group, an indenodibenzothiophene group, a benzofuranofluorene group, a benzofuranocarbazole group, a benzofuranodibenzofuran group, a benzofuranodibenzothiophene group, a benzothiophenofluorene group, a benzothiophenocarbazole group, a benzothiophenodibenzofuran group, and a benzothiophenodibenzothiophene group, but the embodiments of the present disclosure are not limited thereto.

[0066] In formulas 3-1 to 3-5, X 31 Can be N or C(R 31 );X 32 Can be N or C(R 32 );X 33 Can be N or C(R 33 );X 34 Can be N or C(R 34 );X 35 Can be N or C(R 35 );X 36 Can be N or C(R 36 );X 37 Can be N or C(R 37 ); and X 38 Can be N or C(R 38 ), wherein X is selected from Formula 3-1 31 -X 35 At least one of them can be independently N and is selected from X in formula 3-2 to 3-5 36 -X 38 At least one of can be N independently.

[0067] In one embodiment, X selected from Formula 3-1 31 -X 35 Two or three of may be independently N and are selected from X in formula 3-2 to 3-5 36 -X 38 The two of may each independently be N, but the embodiments of the present disclosure are not limited thereto.

[0068] In formulas 3-2 to 3-5, Y 31 Can be selected from O and S.

[0069] In Formulas 1, 2, and 3-1 to 3-5, R 13 、R 14 、R 21 、R 22 , and R 31 -R 39 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C7-C 60 Arylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryloxy, substituted or unsubstituted C1-C 60 Heteroarylthio, substituted or unsubstituted C2-C 60 heteroarylalkyl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q1)(Q2)(Q3), -N(Q4)(Q5), and -B(Q6)(Q7),

[0070] Selected from R 31 -R 39 Two adjacent groups may optionally be linked to each other to form a fused ring, and

[0071] Q1-Q7 can be independently selected from hydrogen, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C1-C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups.

[0072] In one embodiment, in Formula 1, R 13 and R 14 Can be independently selected from:

[0073] hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, anthracenyl, benzo[9,10]phenanthrenyl, pyrenyl, and base; and

[0074] Each of at least one substituted phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, anthracenyl, benzo[9,10]phenanthrenyl, pyrenyl, and Group: deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl, C1-C 20 an alkoxy group, and a phenyl group, but the embodiments of the present disclosure are not limited thereto.

[0075] In one or more embodiments, R in Formula 1 13 and R 14 Can be independently selected from:

[0076] hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, phenyl, biphenyl, terphenyl, and naphthyl; and

[0077] phenyl, biphenyl, terphenyl, and naphthyl, each of which is selected from at least one substituted group selected from the group consisting of deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, and phenyl, but embodiments of the present disclosure are not limited thereto.

[0078] In one or more embodiments, R in Formula 1 13 and R 14 It may be hydrogen, but the embodiments of the present disclosure are not limited thereto.

[0079] In one embodiment, R in Formula 2 21 and R 22 can be independently selected from hydrogen, deuterium, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-difluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetracene, perylenyl, peryl, pentaphenyl, hexacenyl, pentacene, rubinyl, coronenyl, oozolinyl, pyrrolyl, furyl, thienyl, indolyl, benzofuranyl, benzothienyl, carbazolyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothienyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothienyl, indolocarbazolyl, indolodibenzofuranyl, and indolodibenzothienyl; and

[0080] Each of the following is substituted by at least one C1-C 20 Alkyl, C1-C 20Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-difluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetracene, peryl, peryl, pentaphenyl, hexacenyl, pentacene, rubenyl, coronenyl, oozolinyl, pyrrolyl, furyl, thienyl, indolyl, benzofuranyl, benzothienyl, carbazolyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothienyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothienyl, indolocarbazolyl, indolodibenzofuranyl, and indolodibenzothienyl: deuterium, C1-C 20 Alkyl, C1-C 20 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a biphenylcarbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, but embodiments of the present disclosure are not limited thereto.

[0081] In one or more embodiments, R in Formula 2 21 and R 22 Can be independently selected from:

[0082] Hydrogen, deuterium, cyano, C1-C 20 Alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, phenylcarbazolyl, biphenylcarbazolyl, dibenzofuranyl, and dibenzothiophenyl; and

[0083] phenyl and carbazolyl groups each substituted by at least one selected from the group consisting of cyano, C1-C 20 An alkyl group, and a phenyl group, but the embodiments of the present disclosure are not limited thereto.

[0084] In one embodiment, R in Formulas 3-1 to 3-5 31 -R 39 Can be independently selected from:

[0085] hydrogen, phenyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, azadibenzofuranyl, azadibenzothiophenyl, diazadibenzofuranyl, and diazadibenzothiophenyl; and

[0086] phenyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, azadibenzofuranyl, azadibenzothiophenyl, diazadibenzofuranyl, and diazadibenzothiophenyl, each of which is selected from at least one substituted group consisting of deuterium, -F, -Cl, -Br, -I, cyano, C1-C 20 Alkyl, C1-C 20 an alkoxy group, and a phenyl group, but the embodiments of the present disclosure are not limited thereto.

[0087] In one or more embodiments, R in Formulas 3-1 to 3-5 31 -R 39 Can be independently selected from:

[0088] hydrogen, phenyl, biphenyl, terphenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, azadibenzofuranyl, azadibenzothiophenyl, diazadibenzofuranyl, and diazadibenzothiophenyl; and

[0089] phenyl, biphenyl, terphenyl, dibenzofuranyl, dibenzothiophenyl, azadibenzofuranyl, azadibenzothiophenyl, diazadibenzofuranyl, and diazadibenzothiophenyl, each of which is substituted with a phenyl group, but embodiments of the present disclosure are not limited thereto.

[0090] For example, D1 in Formula 1 may be represented by one selected from Formulas 2-1 and 2-2, but embodiments of the present disclosure are not limited thereto:

[0091]

[0092]

[0093] In Formulas 2-1, 2-2, 9-11, 9-21 to 9-23, and 9-31 to 9-48,

[0094] A 21 It may be a group represented by formula 9-11,

[0095] A 22 may be a group represented by one selected from the group consisting of Formulae 9-11, 9-21 to 9-23, and 9-31 to 9-48,

[0096] C1-C4 can each independently be a carbon atom,

[0097] R 21 、R 22 、b 21 and b 22 Can be independently the same as in Formula 2,

[0098] X 91Can be selected from O, S, N (R 22d ), and C(R 22d )(R 22e ),

[0099] X 92 Can be selected from O, S, N (R 22f ), and C(R 22f )(R 22g ),

[0100] R 22a -R 22g Can each independently have the same R as in Formula 2 22 The same definition as the definition of

[0101] b22a-b22c may each independently have the same definition as that of b22 in Formula 2.

[0102] For example, A1 in Formula 1 may be represented by one selected from Formulas 3-11 to 3-35, but embodiments of the present disclosure are not limited thereto:

[0103]

[0104]

[0105] In formulas 3-11 to 3-35,

[0106] Y 31 、R 31 -R 39 , and b39 may each independently have the same definitions as those of Formulae 3-1 to 3-5, and

[0107] * indicates the binding site with the adjacent atom.

[0108] In one embodiment, A1 in Formula 1 may be represented by one selected from Formulas 3-14, 3-15, 3-17, 3-21, 3-25, 3-29, 3-33, 3-34, and 3-35, but embodiments of the present disclosure are not limited thereto.

[0109] For example, the condensed ring compound represented by Formula 1 may be represented by Formula 1-1, but embodiments of the present disclosure are not limited thereto:

[0110] Formula 1-1

[0111]

[0112] In formula 1-1,

[0113] D1, A1, R 11 , and R 12and may each independently have the same definitions as those in Formula 1.

[0114] In one embodiment, in Formula 1-1,

[0115] D1 can be represented by one selected from Formulas 2-1 and 2-2,

[0116] A1 may be represented by one selected from Formulas 3-11 to 3-35, and

[0117] R 11 and R 12 and may each independently have the same definitions as those in Formula 1:

[0118]

[0119]

[0120]

[0121]

[0122] In formulas 2-1, 2-2, 9-11, 9-21 to 9-23, 9-31 to 9-48, and 3-11 to 3-35,

[0123] A 21 It may be a group represented by formula 9-11,

[0124] A 22 may be a group represented by one selected from the group consisting of Formulae 9-11, 9-21 to 9-23, and 9-31 to 9-48,

[0125] C1-C4 can each independently be a carbon atom,

[0126] R 21 、R 22 、b 21 and b 22 Can be independently the same as in Formula 2,

[0127] X 91 Can be selected from O, S, N (R 22d ), and C(R 22d )(R 22e ),

[0128] X 92 Can be selected from O, S, N (R 22f ), and C(R 22f )(R 22g ),

[0129] R 22a -R 22gCan each independently have the same R as in Formula 2 22 The same definition as the definition of

[0130] b22a-b22c may each independently have the same definition as that of b22 in Formula 2,

[0131] Y 31 、R 31 -R 39 , and b39 may each independently have the same definitions as those described in Formulae 3-1 to 3-5, and

[0132] * indicates the binding site with the adjacent atom.

[0133] In one embodiment, the fused ring compound represented by Formula 1 may be selected from Compounds 1 to 1030, but embodiments of the present disclosure are not limited thereto:

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169] The fused ring compound represented by Formula 1 may include a group (A1) represented by one selected from Formulas 3-1 to 3-5 and capable of acting as an electron acceptor group, and a group (D1) represented by Formula 2 and capable of acting as an electron donor group. Therefore, in the fused ring compound represented by Formula 1, HOMO and LUMO may be spatially separated from each other, and thus ΔE ST (At the lowest excited singlet energy level (E S1 ) and the lowest excited triplet energy level (E T1 ) can be reduced. Therefore, the fused ring compound represented by Formula 1 can cause reverse intersystem crossing (RISC) even at a low temperature (eg, room temperature).

[0170] R in Formula 1 11 and R12 is substituted or unsubstituted C6-C 30 Aryl group. Therefore, since the angle formed by the plane including D1 and the plane including A1 in Formula 1 increases (that is, the plane including D1 and the plane including A1 are twisted), the difference between the lowest excited singlet energy level and the lowest excited triplet energy level of the fused ring compound represented by Formula 1 can be reduced. Therefore, the fused ring compound represented by Formula 1 can have high RISC efficiency, so that electronic devices including the fused ring compound, such as organic light-emitting devices, can have high efficiency and / or long life.

[0171] The fused ring compound represented by Formula 1 may satisfy the following Equation 1:

[0172] Equation 1

[0173] 0eV<ΔE ST ≤0.5eV.

[0174] In Equation 1,

[0175] ΔE ST is the lowest excited singlet energy level (E S1 ) and the lowest excited triplet energy level (E T1 ). E T1 and E S1 The structures were evaluated by DFT method using Gaussian program with structural optimization at B3LYP / 6-31G(d,p) level.

[0176] In one embodiment, the fused ring compound represented by Formula 1 may satisfy Equation 1-1, but embodiments of the present disclosure are not limited thereto:

[0177] Equation 1-1

[0178] 0.01eV<ΔE ST ≤0.3eV.

[0179] The lowest excited singlet energy level of the condensed ring compound represented by Formula 1 may be in the range of about 2.5 electron volts (eV) to about 3.0 eV, but embodiments of the present disclosure are not limited thereto.

[0180] In addition, D1 and A1 in the condensed ring compound represented by Formula 1 may be attached to the para position of the phenylene group. Therefore, the condensed ring compound represented by Formula 1 has high oscillator strength, and electronic devices including the condensed ring compound, such as organic light-emitting devices, may have high luminous efficiency.

[0181] For example, some of the HOMO energy levels, LUMO energy levels, T1 energy levels, S1 energy levels, and oscillator strengths of the compounds were evaluated by the DFT method using a Gaussian program (structural optimization performed at the B3LYP / 6-31G(d,p) level), and the results are shown in Table 1.

[0182] Table 1

[0183]

[0184] Referring to Table 1, it is confirmed that the condensed ring compound represented by Formula 1 has a small difference between the singlet energy level and the triplet energy level and a large oscillator strength. Therefore, electronic devices including the condensed ring compound represented by Formula 1, such as organic light-emitting devices, can have high luminous efficiency.

[0185] The synthesis method of the fused ring compound represented by Formula 1 can be recognized by those skilled in the art by referring to the synthesis examples provided below.

[0186] The fused ring compound of Formula 1 can be used as a material for electronic devices, such as organic light-emitting devices. According to another aspect of the exemplary embodiment, the organic light-emitting device includes a first electrode, a second electrode, and an organic layer disposed between the first and second electrodes, wherein the organic layer includes an emission layer and at least one of the fused ring compounds represented by Formula 1 described above.

[0187] Due to including the organic layer including the condensed ring compound represented by Formula 1, the organic light emitting device may have low driving voltage, high efficiency, high brightness, high quantum emission efficiency, and a long lifespan.

[0188] The fused ring compound of Formula 1 can be used between a pair of electrodes of an organic light-emitting device. For example, the fused ring compound can be included in at least one selected from the following: an emission layer, a hole transport region disposed between the first electrode and the emission layer (including, for example, at least one of a hole injection layer, a hole transport layer, a buffer layer, and an electron blocking layer), and an electron transport region disposed between the emission layer and the second electrode (including, for example, at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer).

[0189] The emission layer of the organic light-emitting device may be implemented according to Embodiment 1, 2, or 3 depending on the purpose of the condensed ring compound represented by Formula 1.

[0190] Implementation Method 1

[0191] Embodiment 1 is an embodiment in which the condensed ring compound included in the emission layer is used as a fluorescent emitter, that is, the condensed ring compound is a fluorescent emitter.

[0192] According to embodiment 1, the emission layer is composed of the condensed ring compound; or

[0193] The emission layer may further include a host (hereinafter, referred to as "host A", host A being different from the condensed ring compound).

[0194] Therefore, according to embodiment 1, the ratio of the emission component emitted from the condensed ring compound to the total emission component emitted from the emission layer may be 80% or more, for example, 90% or more. For example, the ratio of the emission component emitted from the condensed ring compound to the total emission component emitted from the emission layer may be 95% or more. The condensed ring compound may emit fluorescence and / or delayed fluorescence, and the emission component of the condensed ring compound is the sum of the prompt emission component of the condensed ring compound and the delayed fluorescence component of the condensed ring compound through reverse intersystem crossing.

[0195] In embodiment 1, when the emission layer further includes a host A in addition to the condensed ring compound, the amount of the condensed ring compound may be about 50 parts by weight or less, for example, about 30 parts by weight or less, based on 100 parts by weight of the emission layer, and the amount of the host A in the emission layer may be about 50 parts by weight or more, for example, about 70 parts by weight or more, based on 100 parts by weight of the emission layer, but the embodiments of the present disclosure are not limited thereto.

[0196] In embodiment 1, when the emission layer further includes a host A in addition to the condensed cyclic compound, the host A and the condensed cyclic compound represented by Formula 1 may satisfy Equation 2:

[0197] Equation 2

[0198] E(H A ) S1 >E S1 .

[0199] In Equation 2,

[0200] E(H A ) S1 is the lowest excited singlet energy level of host A, and

[0201] E S1 is the lowest excited singlet energy level of the fused ring compound represented by Formula 1. A ) S1 and E S1 The structures were evaluated by DFT method using Gaussian program with structural optimization at B3LYP / 6-31G(d,p) level.

[0202] When the fused cyclic compound represented by Formula 1 satisfies Equation 1 and the fused cyclic compound represented by Formula 1 and the host A satisfy Equation 2, the fused cyclic compound represented by Formula 1 may emit fluorescence and / or delayed fluorescence. Therefore, the luminous efficiency of an organic light-emitting device including the fused cyclic compound represented by Formula 1 and the host A may be improved.

[0203] For example, the host A may be a host material described below, but embodiments of the present disclosure are not limited thereto.

[0204] Implementation Method 2

[0205] Embodiment 2 is an embodiment in which the condensed ring compound included in the emission layer is used as a host.

[0206] According to Embodiment 2, the emission layer may include a host and a dopant, and the host may include a condensed ring compound represented by Formula 1. That is, the host is composed of the condensed ring compound represented by Formula 1, or may further include another known host. The dopant may be, for example, a fluorescent dopant, a phosphorescent dopant, or a thermally activated delayed fluorescent dopant.

[0207] Therefore, according to Embodiment 2, the ratio of the emission component of the dopant to the total emission component emitted from the emission layer may be about 80% or more, for example, about 90% or more (in one embodiment, about 95% or more).

[0208] In embodiment 2, the amount of the dopant in the emission layer may be about 50 parts by weight or less, for example, about 30 parts by weight or less, based on 100 parts by weight of the emission layer, and the amount of the host in the emission layer may be about 50 parts by weight or more, for example, about 70 parts by weight or more, based on 100 parts by weight of the emission layer, but the embodiments of the present disclosure are not limited thereto.

[0209] For example, in Embodiment 2, when the dopant includes a fluorescent dopant (hereinafter, referred to as "fluorescent dopant A"), the condensed ring compound represented by Formula 1 and the fluorescent dopant A may satisfy Equation 3:

[0210] Equation 3

[0211] E S1 >E(F A ) S1 .

[0212] In Equation 3,

[0213] E S1 is the lowest excited singlet energy level of the fused ring compound represented by Formula 1, and

[0214] E(F A ) S1is the lowest excited singlet energy level of the fluorescent dopant A.

[0215] E S1 and E(F A ) S1 The structures were evaluated by DFT method using Gaussian program with structural optimization at B3LYP / 6-31G(d,p) level.

[0216] When the fused cyclic compound represented by Formula 1 and the fluorescent dopant A satisfy Equation 3, the Förster energy transfer from the fused cyclic compound represented by Formula 1 to the fluorescent dopant A can be accelerated. Therefore, the luminous efficiency of the organic light-emitting device including the fused cyclic compound represented by Formula 1 and the fluorescent dopant A can be improved.

[0217] For example, the dopant may be a dopant material described below, but embodiments of the present disclosure are not limited thereto.

[0218] When the host further includes another known host, the known host may be a host material described below, but embodiments of the present disclosure are not limited thereto.

[0219] Implementation 3

[0220] Embodiment 3 is an embodiment in which the condensed ring compound in the emission layer is used as an auxiliary dopant.

[0221] According to Embodiment 3, the emission layer may include a host, an auxiliary dopant, and a main dopant, and the auxiliary dopant may include the condensed ring compound. The main dopant may be, for example, a fluorescent dopant, a phosphorescent dopant, or a thermally activated delayed fluorescent dopant.

[0222] Therefore, according to Embodiment 3, the ratio of the emission component of the main dopant to the total emission component emitted from the emission layer may be about 80% or more, for example, about 90% or more (in one embodiment, about 95% or more).

[0223] In embodiment 3, the amount of the main dopant in the emission layer may be about 50 parts by weight or less, for example, about 30 parts by weight or less, based on 100 parts by weight of the emission layer, and the amount of the main body in the emission layer may be about 50 parts by weight or more, for example, about 70 parts by weight or more, based on 100 parts by weight of the emission layer, and the amount of the auxiliary dopant may be about 30 parts by weight or less, for example, about 20 parts by weight or less, based on 100 parts by weight of the emission layer, but the embodiments of the present disclosure are not limited thereto.

[0224] For example, in embodiment 3, when the main dopant is a fluorescent dopant (hereinafter referred to as “fluorescent dopant B”), the host (hereinafter referred to as “host B”), the condensed ring compound represented by Formula 1, and the fluorescent dopant B may satisfy Equation 4:

[0225] Equation 4

[0226] E(H B ) S1 >E S1 >E(F B ) S1 .

[0227] In Equation 4,

[0228] E(H B ) S1 is the lowest excited singlet energy level of the host B,

[0229] E S1 is the lowest excited singlet energy level of the fused ring compound represented by Formula 1, and

[0230] E(F B ) S1 is the lowest excited singlet energy level of the fluorescent dopant B.

[0231] E(H B ) S1 、E S1 , and E(F B ) S1 The results were evaluated by using DFT method with structural optimization at the B3LYP / 6-31G(d,p) level.

[0232] When the host B, the condensed cyclic compound represented by Formula 1, and the fluorescent dopant B satisfy Equation 4, the Förster energy transfer from the condensed cyclic compound represented by Formula 1 to the fluorescent dopant B can be accelerated. Therefore, the luminous efficiency of the organic light-emitting device including the host B, the condensed cyclic compound represented by Formula 1, and the fluorescent dopant B can be improved.

[0233] The host B and the fused ring compound represented by Formula 1 may further satisfy Equation 5:

[0234] Equation 5

[0235] E(H B ) T1 -E T1 >0.05eV.

[0236] In Equation 5,

[0237] E(H B ) T1 is the lowest excited triplet energy level of host B, and

[0238] E T1 is the lowest excited triplet energy level of the fused ring compound represented by Formula 1.

[0239] E(H B ) T1 and E T1 The results were evaluated by using DFT method with structural optimization at the B3LYP / 6-31G(d,p) level.

[0240] In the third embodiment, since Equation 5 is satisfied (for example, E(H B ) T1 -E T1 In the range of about 0.10 eV to about 0.65 eV), the energy of triplet excitons generated in the auxiliary dopant in the emission layer cannot be transferred to the host B in the emission layer, and the possibility that the triplet excitons will be lost by a path other than light emission is reduced. Therefore, the organic light-emitting device can have high efficiency.

[0241] According to Equation 4, the fused ring compound represented by Formula 1 and the fluorescent dopant B may satisfy Equation 6:

[0242] Equation 6

[0243] E(F B ) S1 -E S1 <0eV.

[0244] In Equation 6,

[0245] E(F B ) S1 is the lowest excited singlet energy level of the fluorescent dopant B, and

[0246] E S1 is the lowest excited singlet energy level of the fused ring compound represented by Formula 1.

[0247] E(F B ) S1 and E S1 The results were evaluated by using DFT method with structural optimization at the B3LYP / 6-31G(d,p) level.

[0248] In embodiment 3, when Equation 6 (e.g., E(F B ) S1 -E S1In the range of about -0.4 eV to about -0.05 eV), the energy of the singlet exciton generated in the auxiliary dopant in the emission layer can be quickly transferred to the fluorescent dopant B. Therefore, light emission is basically performed only with the fluorescent dopant B in the emission layer of the organic light-emitting device, and a fluorescence emission spectrum with excellent color purity based on the fluorescent dopant B can be achieved. In addition, since fluorescent emission with a relatively short exciton lifetime is achieved, the efficiency drop phenomenon (so-called roll-off phenomenon) at high brightness caused by the exciton-exciton interaction or the exciton-charge (hole or electron) interaction (exciton-polaron interaction) can be suppressed, thereby achieving an organic light-emitting device with high efficiency. In addition, since the auxiliary dopant has a short exciton lifetime, the possibility of chemical or physical deterioration that may occur in the exciton state of the auxiliary dopant can be reduced, and therefore, the organic light-emitting device satisfying Equation 6 can have improved durability.

[0249] The host in Embodiment 3 may be a host material described below, but embodiments of the present disclosure are not limited thereto.

[0250] The main dopant in Embodiment 3 may be a dopant material described below, but embodiments of the present disclosure are not limited thereto.

[0251] For example, the host may have a triplet energy level of about 2.9 eV or greater, for example, a triplet energy level of about 2.9 eV to about 4.5 eV. Therefore, since energy transfer from the host to the fluorescent dopant, phosphorescent dopant, and / or thermally activated delayed fluorescent dopant is efficiently achieved, the organic light-emitting device may have high efficiency.

[0252] For example, the main body may include at least one compound selected from the following: a compound containing a fluorene group, a compound containing a carbazole group, a compound containing a dibenzofuran group, a compound containing a dibenzothiophene group, a compound containing an indenylcarbazole group, a compound containing an indolecarbazole group, a compound containing a benzofurancarbazole group, a compound containing a benzothiophenecarbazole group, a compound containing an acridine group, a compound containing a dihydroacridine group, a compound containing a triindolephenyl group, a compound containing a pyridine group, a compound containing a pyrimidine group, a compound containing a triazine group, a compound containing a silicon group, a compound containing a cyano group, a compound containing a phosphine oxide group, and a compound containing a sulfoxide group, but the embodiments of the present disclosure are not limited thereto.

[0253] In one embodiment, the host may include a compound including at least one carbazole ring and at least one cyano group.

[0254] For example, the host may be a compound represented by one selected from Formulae 11-1 to 11-3, but embodiments of the present disclosure are not limited thereto:

[0255] Formula 11-1

[0256] Ar 11 -(L 21 ) a21 -(Ar 12 ) c12

[0257] Formula 11-2

[0258]

[0259] Formula 11-3

[0260] T 21 -(L 21 ) a21 -(T 22 ) c12

[0261]

[0262] In Formulas 11-1 to 11-3, 13, and 14,

[0263] Ar 11 and Ar 12 may each independently be a group represented by one selected from Formulae 13 and 14,

[0264] X 15 Can be N(R 200 ), O, or S,

[0265] X 11 Can be N or C(T 14 ), X 12 Can be N or C(T 15 ), and X 13 Can be N or C(T 16 ), wherein X 11 -X 13 At least one of may be each independently N,

[0266] T 21 and T 22 Can be independently selected from *-(L 21 ) a21 -Si(Q 41 )(Q 42 )(Q 43 ) and *-(L 21 ) a21 -P(=O)(Q 51 )(Q52 ),

[0267] L 21 and L 31 -L 33 Can be independently selected from:

[0268] Single bond, O, S, Si(Q 61 )(Q 62 ), phenylene, pyridylene, pyrimidylene, pyrazinylene, pyridazinylene, triazinylene, naphthylene, fluorenylene, carbazolylene, dibenzofuranylene, and dibenzothiophenylene; and

[0269] each being at least one substituted phenylene, pyridylene, pyrimidylene, pyrazinylene, pyridazinylene, triazinylene, naphthylene, fluorenylene, carbazolylene, dibenzofuranylene, and dibenzothiophenylene group, each being selected from the group consisting of deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C 10 Alkyl, C1-C 10 Alkoxy, -CF3, -CF2H, -CFH2, phenyl, phenyl substituted by cyano, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, and -Si(Q 71 )(Q 72 )(Q 73 ),

[0270] a21 and a31-a33 may each independently be an integer of 0-5, wherein when a21 is 2 or greater, two or more groups L 21 They may be the same as or different from each other. When a31 is 2 or greater, two or more groups L 31 They may be the same as or different from each other. When a32 is 2 or greater, two or more groups L 32 may be the same as or different from each other, and when a33 is 2 or greater, two or more groups L 33 may be the same as or different from each other,

[0271] CY 30 and CY 40 may be each independently selected from a phenyl group, a naphthalene group, a fluorene group, a carbazole group, a benzocarbazole group, an indolocarbazole group, a dibenzofuran group, and a dibenzothiophene group,

[0272] A 20 You can choose from:

[0273] single bonds, C1-C4 alkylene, and C2-C4 alkenylene; and

[0274] each being selected from at least one substituted C1-C4 alkylene group, and C2-C4 alkenylene group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C 10 Alkyl, C1-C 10 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, and -Si(Q 81 )(Q 82 )(Q 83 ),and

[0275] T 11 -T 16 、R 200 、R 30 , and R 40 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C7-C 60 Arylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted C1-C 60 Heteroaryloxy, substituted or unsubstituted C1-C 60 Heteroarylthio, substituted or unsubstituted C2-C 60 heteroarylalkyl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, and -Si(Q 91 )(Q 92 )(Q 93 ),

[0276] b30 and b40 can each independently be an integer from 0 to 10,

[0277] c12 can be 0, 1, 2, or 3,

[0278] * indicates the binding site with the adjacent atom,

[0279] The substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkynyl, substituted C3-C 10 Cycloalkyl, substituted C1-C 10 Heterocycloalkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocycloalkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 Aryloxy, substituted C6-C 60 Arylthio, substituted C7-C 60 Aralkyl, substituted C1-C 60 Heteroaryl, substituted C1-C 60 Heteroaryloxy, substituted C1-C 60 Heteroarylthio, substituted C2-C 60 The heteroarylalkyl group, the substituted monovalent non-aromatic fused polycyclic group, and at least one substituent of the substituted monovalent non-aromatic fused heteropolycyclic group may be selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C1-C 60 Heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, C2-C 60 Heteroaralkyl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, and -Si(Q 101 )(Q 102 )(Q103 ),and

[0280] Q 41 -Q 43 , Q 51 -Q 52 , Q 61 -Q 62 , Q 71 -Q 73 , Q 81 -Q 83 , Q 91 -Q 93 , and Q 101 -Q 103 can be independently selected from hydrogen, deuterium, C1-C 60 Alkyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C1-C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups.

[0281] For example, the host may include at least one selected from compounds H-1 to H-27, but embodiments of the present disclosure are not limited thereto:

[0282]

[0283]

[0284]

[0285] The fluorescent dopant may be selected from condensed polycyclic compounds and styryl-based compounds.

[0286] In one embodiment, the fluorescent dopant may include at least one selected from the group consisting of a core containing a naphthalene group, a core containing a fluorene group, a core containing a spiro-bifluorene group, a core containing a benzofluorene group, a core containing a dibenzofluorene group, a core containing a phenanthrene group, a core containing an anthracene group, a core containing a fluoranthene group, a core containing a benzo[9,10]phenanthrene group, a core containing a pyrene group, a core containing a pyrene group, a core containing a phenanthrene group, a core containing a benzo[9,10]phenanthrene ... A core containing a group, a core containing a naphthacene group, a core containing a phenanthracene group, a core containing a perylene group, a core containing a pentaphene group, a core containing an indenoanthracene group, a core containing a naphthacene group, a core containing a dianthracene group, and a core containing a group derived from a compound represented by one selected from Formulae 501-1 to 501-18, but embodiments of the present disclosure are not limited thereto:

[0287]

[0288] In one or more embodiments, the fluorescent dopant may be selected from styryl-amine-based compounds and styryl-carbazole-based compounds, but embodiments of the present disclosure are not limited thereto.

[0289] In one or more embodiments, the fluorescent dopant may be a compound represented by Formula 501:

[0290] Formula 501

[0291]

[0292] In formula 501,

[0293] Ar 501 You can choose from:

[0294] Naphthalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenanthrene group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, group, a naphthacene group, a phenanthracene group, a perylene group, a pentaphene group, an indenoanthracene group, a naphthacene group, a dianthracene group, and a group derived from a compound represented by one selected from Formulae 501-1 to 501-18; and

[0295] Each is selected from at least one substituted naphthyl group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenanthrene group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, a group, a naphthacene group, a phenanthracene group, a perylene group, a pentaphene group, an indenoanthracene group, a naphthacene group, a dianthracene group, and a group derived from a compound represented by one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidine group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C1-C 60 Heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, C2-C 60 Heteroaralkyl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, and -Si(Q 501 )(Q 502 )(Q 503 )(where Q 501 -Q 503 Can be independently selected from hydrogen, C1-C 60 Alkyl, C1-C 60 Alkoxy, C6-C 60 Aryl, C1-C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups),

[0296] L 501 -L 503 Can be independently selected from substituted or unsubstituted C3-C 10 Cycloalkylene, substituted or unsubstituted C1-C 10 Heterocycloalkylene, substituted or unsubstituted C3-C 10 Cycloalkenylene, substituted or unsubstituted C1-C 10 Heterocycloalkenylene, substituted or unsubstituted C6-C 60 Arylene, substituted or unsubstituted C1-C 60 a heteroarylene group, a substituted or unsubstituted divalent non-aromatic fused polycyclic group, and a substituted or unsubstituted divalent non-aromatic fused heteropolycyclic group,

[0297] R 501 and R 502 Can be independently selected from:

[0298] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a carbazole group, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and

[0299] Each of which is selected from at least one substituted phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, yl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, triazinyl, dibenzofuranyl, and dibenzothiophenyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, 1,2-dibenzothiophene, 1,2-dibenzofuranyl, 1,2-dibenzothiophene ...

[0300] xd1-xd3 may each be independently selected from 0, 1, 2, and 3; and

[0301] xd4 can be selected from 0, 1, 2, 3, 4, 5, and 6.

[0302] For example, in Equation 501,

[0303] Ar 501 You can choose from:

[0304] Naphthalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenanthrene group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, group, a naphthacene group, a phenanthracene group, a perylene group, a pentaphene group, an indenoanthracene group, a naphthacene group, a dianthracene group, and a group derived from a compound represented by one selected from Formulae 501-1 to 501-18; and

[0305] Each is selected from at least one substituted naphthyl group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenanthrene group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, a group, a naphthacene group, a phenanthracene group, a perylene group, a pentaphene group, an indenoanthracene group, a naphthacene group, a dianthracene group, and a group derived from a compound represented by one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidine group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C 20 Alkyl, C1-C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, pyridyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, and -Si(Q 501 )(Q 502 )(Q 503 )(where Q 501 -Q 503 can be independently selected from hydrogen, C1-C 20 Alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, and naphthyl),

[0306] L 501 -L 503 Can each independently have 21 The same definition as the definition of

[0307] xd1-xd3 can be independently selected from 0, 1, and 2,

[0308] xd4 may be selected from 0, 1, 2, and 3, but the embodiments of the present disclosure are not limited thereto.

[0309] In one or more embodiments, the fluorescent dopant may include a compound represented by one selected from Formulas 502-1 to 502-5:

[0310] Formula 502-1

[0311]

[0312] Formula 502-2

[0313]

[0314] Formula 502-3

[0315]

[0316] Formula 502-4

[0317]

[0318] Formula 502-5

[0319]

[0320] In formulas 502-1 to 502-5,

[0321] X 51 Can be N or C-[(L 501 ) xd1 -R 501 ], X 52 Can be N or C-[(L 502) xd2 -R 502 ], X 53 Can be N or C-[(L 503 ) xd3 -R 503 ], X 54 Can be N or C-[(L 504 ) xd4 -R 504 ], X 55 Can be N or C-[(L 505 ) xd5 -R 505 ], X 56 Can be N or C-[(L 506 ) xd6 -R 506 ], X 57 Can be N or C-[(L 507 ) xd7 -R 507 ], and X 58 Can be N or C-[(L 508 ) xd8 -R 508 ],

[0322] L 501 -L 508 Can each independently have the same L as in formula 501 501 The same definition as the definition of

[0323] xd1-xd8 may each independently have the same definition as that of xd1 in Formula 501,

[0324] R 501 -R 508 Can be independently selected from:

[0325] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 20 Alkyl, and C1-C 20 Alkoxy,

[0326] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a carbazole group, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and

[0327] Each of which is selected from at least one substituted phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, yl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, triazinyl, dibenzofuranyl, and dibenzothiophenyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, 1,2-dibenzothiophene, 1,2-dibenzofuranyl, 1,2-dibenzothiophene ...

[0328] xd11 and xd12 can each independently be an integer from 0 to 5,

[0329] Selected from R 501 -R 504 The two groups may be optionally linked to each other to form a saturated or unsaturated ring, and

[0330] Selected from R 505 -R 508 The two groups of may be optionally linked to each other to form a saturated or unsaturated ring.

[0331] The fluorescent dopant may include, for example, at least one selected from compounds FD(1) to FD(16) and FD1 to FD13:

[0332]

[0333]

[0334]

[0335]

[0336] Figure 1 FIG. 1 is a schematic diagram of an organic light emitting device 10 according to an embodiment. Figure 1 The structure of an organic light emitting device according to an embodiment and a method of manufacturing the organic light emitting device according to an embodiment are described.The organic light emitting device 10 includes a first electrode 11, an organic layer 15, and a second electrode 19, which are sequentially stacked.

[0337] A substrate may be further provided below the first electrode 11 or above the second electrode 19. As the substrate, any substrate used in a general organic light-emitting device may be used, and the substrate may be a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.

[0338] In one or more embodiments, the first electrode 11 may be formed by depositing or sputtering a material for forming the first electrode 11 on the substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may be selected from a material having a high work function to promote hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode 11 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO). In one or more embodiments, the material for forming the first electrode 11 may be a metal such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag).

[0339] The first electrode 11 may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode 11 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 110 is not limited thereto.

[0340] The organic layer 15 is disposed on the first electrode 11 .

[0341] The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.

[0342] The hole transport region may be disposed between the first electrode 11 and the emission layer.

[0343] The hole transport region may include at least one selected from a hole injection layer, a hole transport layer, an electron blocking layer, and a buffer layer.

[0344] The hole transport region may include only a hole injection layer or a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer / hole transport layer structure or a hole injection layer / hole transport layer / electron blocking layer structure, which are sequentially stacked in this order starting from the first electrode 11.

[0345] When the hole transport region includes a hole injection layer (HIL), the HIL may be formed on the first electrode 11 by using one or more suitable methods such as vacuum deposition, spin coating, casting, and / or Langmuir-Blodgett (LB) deposition.

[0346] When the hole injection layer is formed by vacuum deposition, the deposition conditions may vary depending on the material used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature of about 100° C. to about 500° C., a ... -8 Torr - about 10 -3 Torr vacuum pressure, and approx. / second - approx. However, the deposition conditions are not limited thereto.

[0347] When the hole injection layer is formed using spin coating, the coating conditions may vary depending on the material used to form the hole injection layer, and the structure and thermal properties of the hole injection layer. For example, the coating speed may be about 2,000 revolutions per minute (rpm) to about 5,000 rpm, and the temperature for heat treatment after coating to remove the solvent may be about 80° C. to about 200° C. However, the coating conditions are not limited thereto.

[0348] The conditions for forming the hole transport layer and the electron blocking layer can be understood by referring to the conditions for forming the hole injection layer.

[0349] The hole transport region may include at least one selected from the group consisting of m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by the following Formula 201, and a compound represented by Formula 202:

[0350]

[0351]

[0352] Formula 201

[0353]

[0354] Formula 202

[0355]

[0356] In formula 201,

[0357] Ar 101 and Ar 102 Can be independently selected from:

[0358] Phenylene, cyclopentadienylene, indenylene, naphthylene, azulenylene, heptalenylene, acenaphthenylene, fluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyren ... benzo[9,10]phenanthrenylene, pyrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phen phenylene, tetraphenylene, perylenene, and pentacene; and

[0359] Each of the following is selected from at least one substituted phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, acenaphthenylene, fluorenylene, phenalenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, acenaphthenylene, fluor ...benzo[9,10]phenanthrenylene, pyrenylene, acenaphthenylene, fluorenylene, phenanthrenylene, phenanthrenylene, fluorenylene, benzo[9,10]phenanthrenyl phenylene, tetraphenylene, perylenene, and pentacene: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C1-C 60 Heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, C2-C 60 heteroarylalkyl, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heteropolycyclic group, and

[0360] xa and xb may each independently be an integer of 0 to 5, or 0, 1 or 2, wherein xa may be 1 and xb may be 0, but xa and xb are not limited thereto.

[0361] In Equations 201 and 202, R 101 -R 108 、R 111 -R 119 , and R 121 -R 124 Can be independently selected from:

[0362] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 10 Alkyl (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.), and C1-C 10 Alkoxy (e.g., methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.);

[0363] Each of the following is substituted by at least one C1-C 10 Alkyl and C1-C 10 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, and phosphoric acid or its salt;

[0364] phenyl, naphthyl, anthracenyl, fluorenyl, or pyrenyl; or

[0365] phenyl, naphthyl, anthracenyl, fluorenyl, and pyrenyl, each of which is selected from at least one substituted group consisting of deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C 10 Alkyl, and C1-C 10 Alkoxy,

[0366] However, the embodiments of the present disclosure are not limited thereto.

[0367] In formula 201, R 109 You can choose from:

[0368] phenyl, naphthyl, anthracenyl, and pyridyl; and

[0369] phenyl, naphthyl, anthracenyl, and pyridyl groups, each of which is substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C 20 Alkyl, C1-C 20 alkoxy, phenyl, naphthyl, anthracenyl, and pyridyl.

[0370] In one embodiment, the compound represented by Formula 201 may be represented by Formula 201A, but embodiments of the present disclosure are not limited thereto:

[0371] Formula 201A

[0372]

[0373] In Formula 201A, R 101 、R111 、R 112 , and R 109 May each independently have the same definition as described above.

[0374] For example, the compound represented by Formula 201 and the compound represented by Formula 202 may include compounds HT1 to HT20, but are not limited thereto:

[0375]

[0376]

[0377] The thickness of the hole transport region may be about -about For example, about about When the hole transport region includes both a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be about -about For example, about -about and the thickness of the hole transport layer may be in the range of about -about For example, about -about While not wishing to be bound by theory, it is understood that when the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics can be obtained without a significant increase in driving voltage.

[0378] In addition to these materials, the hole transport region may further include a charge generating material for improving conductive properties. The charge generating material may be dispersed uniformly or non-uniformly in the hole transport region.

[0379] The charge generating material may be, for example, a p-dopant. The p-dopant may be one selected from a quinone derivative, a metal oxide, and a compound containing a cyano group, but the embodiments of the present disclosure are not limited thereto. Non-limiting examples of the p-dopant include quinone derivatives such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); metal oxides such as tungsten oxide or molybdenum oxide; and compounds containing a cyano group such as compounds HT-D1 or HP-1, but are not limited thereto.

[0380]

[0381] HP-1

[0382]

[0383] The hole transport region may include a buffer layer.

[0384] Furthermore, the buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer, and thus, may improve efficiency of the formed organic light emitting device.

[0385] The hole transport region may further include an electron blocking layer. The electron blocking layer may include, for example, mCP, but the material thereof is not limited thereto.

[0386]

[0387] Then, an emission layer may be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, etc. When the emission layer is formed by vacuum deposition or spin coating, the deposition or coating conditions may be similar to those applied when forming the hole injection layer, although the deposition or coating conditions may vary depending on the compound used to form the emission layer.

[0388] When the organic light-emitting device is a full-color organic light-emitting device, the emission layer can be patterned into a red emission layer, a green emission layer, and a blue emission layer. In one or more embodiments, due to the stacked structure including the red emission layer, the green emission layer, and / or the blue emission layer, the emission layer can emit white light.

[0389] The emission layer is the same as described above.

[0390] The thickness of the emission layer may be about -about For example, about -about While not wishing to be bound by theory, it is understood that when the thickness of the emission layer is within this range, excellent light emitting characteristics may be obtained without a significant increase in driving voltage.

[0391] Then, an electron transport region may be provided on the emission layer.

[0392] The electron transport region may include at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer.

[0393] For example, the electron transport region may have a hole blocking layer / electron transport layer / electron injection layer structure or an electron transport layer / electron injection layer structure, but the structure of the electron transport region is not limited thereto. The electron transport layer may have a multilayer structure or a single layer structure including two or more different materials.

[0394] Conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer constituting the electron transport region can be understood by referring to the conditions for forming the hole injection layer.

[0395] When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of BCP and Bphen, but may also include other materials.

[0396]

[0397] The hole blocking layer may include a compound selected from the hosts described above. For example, the hole blocking layer may include compound H19, but may also include other compounds.

[0398] The thickness of the hole blocking layer may be about -about For example, about -about While not wishing to be bound by theory, it is understood that when the thickness of the hole blocking layer is within these ranges, the hole blocking layer may have excellent hole blocking characteristics without a significant increase in driving voltage.

[0399] The electron transport layer may include at least one selected from the group consisting of BCP, Bphen, Alq3, BAlq, TAZ, and NTAZ.

[0400]

[0401] In one or more embodiments, the electron transport layer may include at least one selected from compounds ET1, ET2, and ET3, but embodiments of the present disclosure are not limited thereto:

[0402]

[0403] The thickness of the electron transport layer can be about -about For example, about -about Although not wishing to be bound by theory, it is understood that when the thickness of the electron transport layer is within the above range, the electron transport layer may have satisfactory electron transport characteristics without a significant increase in driving voltage.

[0404] In addition, the electron transport layer may further include a material containing a metal in addition to the above-mentioned materials.

[0405] The metal-containing material may include a Li complex, such as ET-D1 (lithium 8-hydroxyquinoline, LiQ) or ET-D2.

[0406]

[0407] The electron transport region may include an electron injection layer (EIL) that facilitates the flow of electrons from the second electrode 19 thereinto.

[0408] The electron injection layer may include at least one selected from the group consisting of LiF, NaCl, CsF, Li2O, and BaO.

[0409] The thickness of the electron injection layer can be about -about For example, about -about While not wishing to be bound by theory, it is understood that when the thickness of the electron injection layer is within the above range, the electron injection layer may have satisfactory electron injection characteristics without a significant increase in driving voltage.

[0410] A second electrode 19 is provided on the organic layer 15. The second electrode 19 may be a cathode. The material used to form the second electrode 19 may be a metal, an alloy, a conductive compound, or a combination thereof having a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag) may be used as the material for forming the second electrode 19. In order to manufacture a top-emitting light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.

[0411] In the above, reference has been made to Figure 1 The organic light emitting device is described, but embodiments of the present disclosure are not limited thereto.

[0412] As used herein, the term "C1-C 60 "Alkyl" refers to a linear or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl. As used herein, the term "C1-C 60 "Alkylene" refers to a group having a C1-C 60 Alkyl is a divalent group of the same structure.

[0413] As used herein, the term "C1-C 60 "Alkoxy" refers to a group consisting of -OA 101 The monovalent group represented by 101 C1-C 60 alkyl), and examples thereof include methoxy, ethoxy, and isopropoxy.

[0414] As used herein, the term "C2-C 60"Alkenyl" refers to a C2-C 60 The term "C2-C4" as used herein refers to a hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminal of the alkyl group, and examples thereof include vinyl, propenyl, and butenyl. 60 "Alkenylene" refers to a group having a C2-C 60 Alkenyl is a divalent group of the same structure.

[0415] As used herein, the term "C2-C 60 "Alkynyl" refers to a C2-C 60 The term "C2-C4" as used herein refers to a hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the terminal of the alkyl group, and examples thereof include ethynyl and propynyl. 60 "Alkynylidene" refers to a C2-C 60 Alkynyl is a divalent group of the same structure.

[0416] As used herein, the term "C3-C 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. As used herein, the term "C3-C 10 "Cycloalkylene" refers to a group having a C3-C 10 Cycloalkyl is a divalent group of the same structure.

[0417] As used herein, the term "C2-C 10 "Heterocycloalkyl" refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, P, Si and S as a ring atom and 2 to 10 carbon atoms, and non-limiting examples thereof include tetrahydrofuranyl and tetrahydrothienyl. As used herein, the term "C1-C 10 "Heterocycloalkylene" refers to a 10 Heterocycloalkyl is a divalent group of the same structure.

[0418] As used herein, the term "C3-C 10 "Cycloalkenyl" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and having no aromaticity, and non-limiting examples thereof include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C3-C 10 "Cycloalkenylene" refers to a group having a C3-C 10 Cycloalkenyl is a divalent group of the same structure.

[0419] As used herein, the term "C2-C 10"Heterocycloalkenyl" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, P, Si, and S as a ring atom, 2 to 10 carbon atoms, and at least one double bond in its ring. 10 Examples of heterocycloalkenyl groups are 2,3-dihydrofuranyl, and 2,3-dihydrothienyl. 10 "Heterocycloalkenylene" refers to a C2-C 10 Heterocycloalkenyl is a divalent group of the same structure.

[0420] As used herein, the term "C6-C 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the term "C6-C 60 "Arylene" refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. 60 Non-limiting examples of aryl groups include phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, and When C6-C 60 Aryl and C6-C 60 When the arylene groups each include two or more rings, the rings may be fused to each other.

[0421] As used herein, the term "C2-C 60 "Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system having at least one heteroatom selected from N, O, P, Si, and S as a ring atom and 2 to 60 carbon atoms. As used herein, the term "C2-C 60 "Heteroarylene" refers to a divalent group having a heterocyclic aromatic system having at least one heteroatom selected from N, O, P, Si, and S as a ring atom and 2 to 60 carbon atoms. 60 Non-limiting examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. 60 Heteroaryl and C2-C 60 When the heteroarylene groups each include two or more rings, the rings may be fused to each other.

[0422] As used herein, the term "C6-C 60 "Aryloxy" refers to -OA 102 (where A 102 C6-C 60 aryl), and as used herein C6-C 60 Arylthio represents -SA 103 (where A 103 C6-C 60 aryl), and as used herein, the term "C7-C60 Aralkyl" means -A 104 A 105 (where A 105 C6-C 59 Aryl and A 104 C1-C 54 alkylene).

[0423] As used herein, the term "C1-C 60 "Heteroaryloxy" refers to -OA 106 (where A 106 C1-C 60 heteroaryl), such as the term "C1-C 60 "Heteroarylthio" means -SA 107 (where A 107 C1-C 60 heteroaryl), and as used herein, the term "C2-C 60 "Heteroaralkyl" refers to -A 108 A 109 (A 109 C1-C 59 Heteroaryl, and A 108 C1-C 59 alkylene).

[0424] As used herein, the term "monovalent non-aromatic fused polycyclic group" refers to a monovalent group having two or more rings fused to each other, having only carbon atoms (e.g., the number of carbon atoms may be in the range of 8-60) as ring atoms, and not having aromaticity in its entire molecular structure. Non-limiting examples of the monovalent non-aromatic fused polycyclic group include fluorenyl. As used herein, the term "divalent non-aromatic fused polycyclic group" refers to a divalent group having the same structure as the monovalent non-aromatic fused polycyclic group.

[0425] As used herein, the term "monovalent non-aromatic fused heteropolycyclic group" refers to a monovalent group having two or more rings fused to each other, having, in addition to carbon atoms (e.g., the number of carbon atoms may be in the range of 2-60), heteroatoms selected from N, O, P, Si, and S as ring-forming atoms, and having no aromaticity in its entire molecular structure. Non-limiting examples of the monovalent non-aromatic fused heteropolycyclic group include carbazolyl. As used herein, the term "divalent non-aromatic fused heteropolycyclic group" refers to a divalent group having the same structure as the monovalent non-aromatic fused heteropolycyclic group.

[0426] Substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkynyl, substituted C1-C60 Alkoxy, substituted C3-C 10 Cycloalkyl, substituted C1-C 10 Heterocycloalkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocycloalkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 Aryloxy, substituted C6-C 60 Arylthio, substituted C7-C 60 Aralkyl, substituted C1-C 60 Heteroaryl, substituted C1-C 60 Heteroaryloxy, substituted C1-C 60 Heteroarylthio, substituted C2-C 60 At least one substituent of the heteroaralkyl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group may be selected from:

[0427] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, and C1-C 60 alkoxy;

[0428] Each of the following is substituted by at least one C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, and C1-C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C1-C 60 Heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60Heteroarylthio, C2-C 60 Heteroaralkyl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 ), and -P(=O)(Q 18 )(Q 19 );

[0429] C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C1-C 60 Heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, C2-C 60 heteroaralkyl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups;

[0430] Each of the following is substituted by at least one C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C1-C 60 Heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, C2-C 60 Heteroaralkyl, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C1-C 60 Heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, C2-C 60 Heteroaralkyl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 22 )、-Si(Q 23 )(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 ), and -P(=O)(Q 28 )(Q 29 );and

[0431] -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 ), and -P(=O)(Q 38 )(Q 39 ),and

[0432] Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -Q 39 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C10 Heterocycloalkenyl, C6-C 60 Aryl, selected from C1-C 60 Alkyl and C6-C 60 At least one substituted C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C1-C 60 Heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroarylthio, C2-C 60 heteroaralkyl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups.

[0433] As used herein, the term "room temperature" refers to about 25°C.

[0434] Hereinafter, the fused ring compound and the organic light-emitting device according to the embodiment will be described in detail with reference to Synthesis Examples and Examples. However, the fused ring compound and the organic light-emitting device are not limited thereto. The phrase "using 'B' instead of 'A'" used in describing the Synthesis Examples means that the molar equivalent of 'B' is the same as the molar equivalent of 'A'.

[0435] Example

[0436] Synthesis Example 1: Synthesis of Compound 3

[0437] Compound 3 was synthesized according to the following reaction scheme:

[0438]

[0439] Synthesis of intermediate 3(1)

[0440] Phenylboronic acid (63.43 grams (g), 520.22 millimoles (mmol)), 1,3-dibromo-5-chloro-2-fluorobenzene (50 g, 173.41 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh 3 ) 4) (20.04 g, 17.34 mmol), potassium carbonate (K 2 CO 3) (95.87 g, 693.63 mmol), and S-phos (14.24 g, 34.68 mmol) were added to 300 milliliters (ml) of tetrahydrofuran and 300 ml of distilled water, and the resulting mixture was heated under reflux. After completion of the reaction, the reaction product was cooled to room temperature, and an organic layer was extracted therefrom using ethyl acetate, dried over anhydrous sodium sulfate (Na 2 SO 4 ), concentrated, and then separated by silica gel column chromatography (dichloromethane / hexane). The solid obtained therefrom was recrystallized by using hexane to obtain Intermediate 3(1) (40.7 g, 143.81 mmol, 83% yield) as a white solid.

[0441] Synthesis of intermediate 3(2)

[0442] Intermediate 3(1) (40.7 g, 143.81 mmol), bis(pinacolato)diboron (54.78 g, 215.71 mmol), potassium acetate (35.29 g, 359.52 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3)) (13.17 g, 14.38 mmol), and tricyclohexylphosphine (4.03 g, 14.38 mmol) were added to 290 ml of dioxane, and the resulting mixture was heated under reflux. After the reaction was completed, the reaction product was cooled to room temperature, dissolved in a large amount of toluene, and filtered through silica gel. The organic layer obtained therefrom was concentrated, precipitated by pouring hexane thereto, and filtered to obtain Intermediate 3(2) (47.0 g, 125.58 mmol, 87% yield) as a white solid.

[0443] Synthesis of intermediate 3(3)

[0444] 2-Chloro-4,6-diphenyl-1,3,5-triazine (18 g, 67.23 mmol), intermediate 3(2) (30.2 g, 80.68 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (3.89 g, 3.36 mmol), potassium carbonate (K2CO3) (18.59 g, 134.47 mmol), and S-phos (5.52 g, 13.45 mmol) were added to 120 ml of tetrahydrofuran and 120 ml of distilled water, and the resulting mixture was heated under reflux. After completion of the reaction, the reaction product was cooled to room temperature, and methanol was added thereto. The reaction product was filtered through silica gel. The organic layer obtained therefrom was concentrated and precipitated by pouring methanol thereto to synthesize intermediate 3(3) (30.0 g, 62.56 mmol, 93% yield) as a white solid.

[0445] Synthesis of compound 3

[0446] Intermediate 3 (3) (4.80 g, 10 mmol), 3,6-di-tert-butyl-9H-carbazole (4.19 g, 15 mmol), and cesium carbonate (Cs2CO3) (6.52 g, 20 mmol) were added to 20 ml of N,N-dimethylformamide, and the resulting mixture was stirred at a temperature of 165°C for 20 hours. After the reaction was completed, the reaction product was cooled to room temperature, and methanol was added thereto. The reaction product was filtered through silica gel. The organic layer obtained therefrom was concentrated, dissolved again in toluene, filtered through silica gel, and concentrated. The resulting product was recrystallized (ethyl acetate / ethanol) to synthesize compound 3 (7.89 g, 10.68 mmol, 97% yield) as a yellow solid.

[0447] LC-MS (calculated: 738.37 g / mol, found: 739.35 g / mol (M+1)).

[0448] Synthesis Example 2: Synthesis of Compound 4

[0449] Compound 4 was synthesized in the same manner as in the synthesis of Compound 3 (yield of 68%), except that 3,6-diphenyl-9H-carbazole was used instead of 3,6-di-tert-butyl-9H-carbazole.

[0450] LC-MS (calculated: 778.31 g / mol, found: 779.32 g / mol (M+1)).

[0451] Synthesis Example 3: Synthesis of Compound 23

[0452] Compound 23 (58% yield) was synthesized in the same manner as in the synthesis of Compound 3 in Synthesis Example 1, except that 5H-benzofuro[3,2-c]carbazole was used instead of 3,6-dibutyl-9H-carbazole.

[0453] LC-MS (calculated: 716.26 g / mol, found: 717.26 g / mol (M+1)).

[0454] Synthesis Example 4: Synthesis of Compound 41

[0455] Compound 41 was synthesized in the same manner as in Synthesis Example 1 (yield of 52%), except that 9H-3,9′-bicarbazole was used instead of 3,6-di-tert-butyl-9H-carbazole in the synthesis of Compound 3.

[0456] LC-MS (calculated: 791.30 g / mol, found: 792.31 g / mol (M+1)).

[0457] Synthesis Example 5: Synthesis of Compound 174

[0458] Synthesis of intermediate 174(3)

[0459]

[0460] Intermediate 174(3) was synthesized in the same manner as in the synthesis of Intermediate 3(3) in Synthesis Example 1 (83% yield), except that 4-bromo-2,6-diphenylpyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine in the synthesis of Intermediate 3(3).

[0461] Synthesis of intermediate 174(4)

[0462]

[0463] Intermediate 174(4) was synthesized in the same manner as in the synthesis of compound 3 in Synthesis Example 1 (94% yield), except that intermediate 174(3) was used instead of intermediate 3(3) and 5,12-dihydroindole[3,2-a]carbazole was used instead of 3,6-di-tert-butyl-9H-carbazole.

[0464] Synthesis of compound 174

[0465] Intermediate 174(4) (6.8 g, 9.51 mmol), bromobenzene (8.96 g, 57.1 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (3.48 g, 3.8 mmol), sodium tert-butoxide (3.66 g, 38.05 mmol), and tri-tert-butylphosphine (1.54 g, 7.61 mmol) were added to 50 ml of toluene, and the resulting mixture was stirred at a temperature of 130°C for 12 hours. After the reaction was completed, the reaction product was cooled to room temperature, and methanol was added thereto. The reaction product was filtered and dried. The resulting solid was separated by silica gel column chromatography (dichloromethane / hexane) and recrystallized (methanol) to synthesize compound 174 (4.26 g, 5.39 mmol, 57% yield) as a yellow solid.

[0466] LC-MS (calculated: 790.31 g / mol, found: 791.28 g / mol (M+1)).

[0467] Synthesis Example 6: Synthesis of Compound 209

[0468] Compound 209 was synthesized in the same manner as in Synthesis Example 1 (81% yield), except that Intermediate 174(3) was used instead of Intermediate 3(3), and 5-phenyl-5,10-dihydrofuro[3,2-c:4,5-c′]dicarbazole was used instead of 3,6-di-tert-butyl-9H-carbazole.

[0469] LC-MS (calculated: 880.32 g / mol, found: 881.36 g / mol (M+1)).

[0470] Synthesis Example 7: Synthesis of Compound 229

[0471] Synthesis of intermediate 229(3)

[0472]

[0473] Intermediate 229(3) was synthesized in the same manner as in the synthesis of intermediate 3(3) of Synthesis Example 1 (79% yield), except that 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0474] Synthesis of compound 229

[0475] Compound 229 was synthesized in the same manner as in the synthesis of compound 3 of Synthesis Example 1 (65% yield), except that intermediate 229(3) was used instead of intermediate 3(3), and 3,6-diphenyl-9H-carbazole was used instead of 3,6-di-tert-butyl-9H-carbazole.

[0476] LC-MS (calculated: 930.37 g / mol, found: 931.37 g / mol (M+1)).

[0477] Synthesis Example 8: Synthesis of Compound 481

[0478] Synthesis of intermediate 481(3)

[0479]

[0480] Intermediate 481(3) was synthesized in the same manner as in the synthesis of intermediate 3(3) of Synthesis Example 1 (84% yield), except that 2,4-dichlorobenzofurano[3,2-d]pyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine in the synthesis of intermediate (3), and the reaction temperature was 55°C.

[0481] Synthesis of intermediate 481(4)

[0482]

[0483] Intermediate 481(3) (6.2 g, 13.75 mmol), phenylboronic acid (2.52 g, 20.63 mmol), palladium acetate (Pd(OAc)2) (0.062 g, 0.28 mmol), sodium carbonate (Na2CO3) (2.92 g, 27.5 mmol), and S-Phos (0.23 g, 0.55 mmol) were added to 130 ml of toluene, 65 ml of ethanol, and 50 ml of water, and the resulting mixture was stirred at a temperature of 60°C for 4 hours. After the reaction was completed, extraction was performed by using toluene, and the product was filtered. Then, the solvent was removed therefrom. Recrystallization (dichloromethane / methanol) was performed to obtain intermediate 481(4) as a white solid (96% yield).

[0484] Synthesis of compound 481

[0485] Compound 481 was synthesized in the same manner as in the synthesis of compound 3 in Synthesis Example 1 (32% yield), except that intermediate 481 (4) was used instead of intermediate 3 (3) in the synthesis of compound 3, and 7H-benzofurano[2,3-b]carbazole was used instead of 3,6-di-tert-butyl-9H-carbazole in the synthesis of compound 3.

[0486] LC-MS (calculated: 729.24 g / mol, found: 730.23 g / mol (M+1)).

[0487] Synthesis Example 9: Synthesis of Compound 617

[0488] Compound 617 was synthesized according to the following reaction scheme.

[0489]

[0490] Synthesis of intermediate 617(1)

[0491] Intermediate 617(1) was synthesized in the same manner as in the synthesis of intermediate 3(1) in Synthesis Example 1 (96% yield), except that 4-tert-butylphenylboronic acid was used instead of phenylboronic acid, and 2-bromo-4-chloro-1-fluorobenzene was used instead of 1,3-dibromo-5-chloro-2-fluorobenzene.

[0492] Synthesis of intermediate 617(2)

[0493] Intermediate 617 (1) (27.6 g, 105.04 mmol) and triisopropyl borate (29.63 g, 157.56 mmol) were dissolved in 200 ml of tetrahydrofuran, and the resulting mixture was stirred at a temperature of -78°C for 30 minutes (solution 1). 2,2,6,6-Tetramethylpiperidine (19.3 g, 136.56 mmol) was added to 150 ml of tetrahydrofuran and stirred at a temperature of 0°C. n-Butyllithium (n-BuLi) (78.8 ml of a 1.6 molar (M) solution, 126.05 mmol) was slowly added thereto, and the resulting mixture was stirred at a temperature of 0°C for 30 minutes. The resulting lithium tetramethylpiperidinium (LiTMP) solution was added to solution 1 at a temperature of -78°C, heated to a temperature of -60°C and the resulting mixture was stirred for 1 hour, then heated to a temperature of -50°C and the resulting mixture was stirred for 1 hour. After the solution was further stirred at room temperature for 4 hours, the solvent was removed therefrom. 500 ml of 1 normal (N) hydrochloric acid (HCl) was added thereto and the resulting mixture was stirred for 20 hours. The product was extracted with ethyl acetate, the combined organic extracts were dried over anhydrous sodium sulfate (MgSO 4 ), and the solvent was removed in vacuo. Recrystallization (dichloromethane / hexane) provided intermediate 617 (2) (100% yield).

[0494] Synthesis of intermediate 617(3)

[0495] Intermediate 617(2) (11.37 g, 37.09 mmol), bromobenzene (7.0 g, 44.51 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (2.14 g, 1.85 mmol), and sodium carbonate (Na2CO3) (7.86 g, 74.18 mmol) were added to 40 ml of toluene, 20 ml of ethanol, and 40 ml of water, and the resulting mixture was stirred at a temperature of 80°C for 20 hours. The product was extracted by using toluene, the combined organic extracts were dried by using anhydrous magnesium sulfate (MgSO4), and the solvent was removed in vacuo. The product was then purified by silica gel column chromatography using hexane as eluent to obtain intermediate 617(3) (84% yield).

[0496] Synthesis of intermediate 617(4)

[0497] Intermediate 617(4) was synthesized in the same manner as in the synthesis of Intermediate 3(2) of Synthesis Example 1 (yield of 48%), except that Intermediate 617(3) was used instead of Intermediate 3(1).

[0498] Synthesis of intermediate 617(5)

[0499] Intermediate 617(5) was synthesized in the same manner as in the synthesis of Intermediate 3(3) of Synthesis Example 1 (yield of 91%), except that Intermediate 617(4) was used instead of Intermediate 3(2).

[0500] Synthesis of compound 617

[0501] Compound 617 (73% yield) was synthesized in the same manner as in the synthesis of compound 3 of Synthesis Example 1, except that intermediate 617(5) was used instead of intermediate 3(3), and 3,6-diphenyl-9H-carbazole was used instead of 3,6-di-tert-butyl-9H-carbazole.

[0502] LC-MS (calculated: 834.37 g / mol, found: 835.37 g / mol (M+1)).

[0503] Synthesis Example 10: Synthesis of Compound 796

[0504] Compound 796 (49% yield) was synthesized in the same manner as in the synthesis of Compound 3 of Synthesis Example 1, except that biphenylboronic acid ([1,1′-biphenyl]-4-ylboronic acid) was used instead of phenylboronic acid, and 3,6-diphenyl-9H-carbazole was used instead of 3,6-di-tert-butyl-9H-carbazole.

[0505] LC-MS (calculated: 930.37 g / mol, found: 931.37 g / mol (M+1)).

[0506] Synthesis Example 11: Synthesis of Compound 889

[0507] Synthesis of intermediate 889(1)

[0508]

[0509] 2-Biphenyl-4,6-dichloro-1,3,5-triazine (7 g, 23.17 mmol), [1,1':3',1"-terphenyl]-5'-ylboronic acid (6.35 g, 23.17 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (0.535 g, 0.46 mmol), and sodium carbonate (Na2CO3) (4.911 g, 46.33 mmol) were added to 25 ml of toluene, 25 ml of dioxane, and 25 ml of water, and the resulting mixture was stirred at a temperature of 80°C for 20 hours. After adding toluene thereto, the product obtained therefrom was filtered through silica gel and recrystallized by using toluene to obtain Intermediate 889(1) (52% yield).

[0510] Synthesis of compound 889

[0511] Compound 889 was synthesized in the same manner as in the synthesis of compound 3 in Synthesis Example 1 (68% yield), except that intermediate 889(1) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and 3,6-diphenyl-9H-carbazole was used instead of 3,6-di-tert-butyl-9H-carbazole.

[0512] LC-MS (calculated: 1006.40 g / mol, found: 1007.36 g / mol (M+1)).

[0513] Synthesis Example 12: Synthesis of Compound 57

[0514] Compound 57 was synthesized in the same manner as in Synthesis Example 1 (yield of 67%) except that 6- 3,6-di-tert-butyl-9H-carbazole was replaced by butyl-9H-3,9'-bicarbazole.

[0515] LC-MS (calculated: 909.38 g / mol, found: 910.37 g / mol (M+1)).

[0516] Synthesis Example 13: Synthesis of Compound 75

[0517] Compound 75 was synthesized in the same manner as in Synthesis Example 1 (yield of 96%), except that 11-phenyl-5H-benzofuro[3,2-c]carbazole was used instead of 3,6-di-tert-butyl-9H-carbazole.

[0518] LC-MS (calculated: 792.29 g / mol, found: 793.29 g / mol (M+1)).

[0519] Evaluation Example 1

[0520] The photoluminescence (PL) spectra, HOMO energy level, LUMO energy level, lowest excited singlet state (S1) energy level, lowest excited triplet state (T1) energy level, and ΔE of compounds 3, 4, 23, 41, 174, 209, 229, 481, 617, 796, 889, 57, 75, and A were evaluated according to the methods shown in Table 2. ST , and the results are shown in Table 3.

[0521]

[0522] Table 2

[0523]

[0524] Table 3

[0525]

[0526]

[0527] Referring to Table 3, it was confirmed that compounds 3, 4, 23, 41, 174, 209, 229, 481, 617, 796, 889, 57, and 75 can emit deep blue light and have a small ΔE ST And it emits thermally activated delayed fluorescence light.

[0528] Evaluation Example 2

[0529] Compound H19 and compound 3 (15 weight percent, wt%) were co-deposited on a quartz cell to produce a Film 1 was prepared with a thickness of 100 nm. Films 2 to 13, A, and B were prepared in the same manner as described above, except that compounds 4, 23, 41, 174, 209, 229, 481, 617, 796, 889, 57, 75, A, and B were used instead of compound 3. Then, films 1 to 13, A, and B were excited by excitation light having a wavelength of 340 nanometers (nm) under a nitrogen atmosphere using C9920-02 and PMA-11 (manufactured by Hamamatsu photonics), and the PL quantum efficiency (quantum yield) of each film was measured. The results are shown in Table 4.

[0530] Table 4

[0531]

[0532]

[0533] Referring to Table 4, it was confirmed that films 1 to 13 had higher PL quantum efficiencies than films A and B.

[0534] Example 1

[0535] Formed on it The glass substrate of thick ITO electrode (first electrode, anode) is washed by ultrasonic wave with distilled water. When finishing washing with distilled water, ultrasonic wave washing is carried out by sequentially using isopropyl alcohol, acetone and methanol. The resultant is dried, then transferred to a plasma washer, and the obtained substrate is washed with plasma for 5 minutes, then transferred to a vacuum deposition device.

[0536] Compound HT3 was vacuum deposited on the ITO electrode on the glass substrate to form a The first hole injection layer is formed by vacuum-depositing compound HT-D1 on the first hole injection layer to form a and depositing mCP on the second hole injection layer to form a second hole injection layer having a thickness of An electron blocking layer with a thickness of , thereby forming a hole transport region.

[0537] Compound H19 (host) and compound 3 (dopant) were co-deposited on the hole transport region at a volume ratio of 85:15 to form a The thickness of the emission layer.

[0538] Compound ET3 is vacuum deposited on the emission layer to form An electron transport layer having a thickness of , ET-D1(LiQ) is deposited on the electron transport layer to form a An electron injection layer having a thickness of , and Al is deposited on the electron injection layer to form An Al second electrode (cathode) with a thickness of is formed, thereby completing the manufacture of the organic light-emitting device.

[0539]

[0540] Examples 2-13 and Comparative Examples AC

[0541] An organic light-emitting device was manufactured in the same manner as in Example 1, except that in forming the emission layer, the compounds shown in Table 5 were each used as a dopant instead of Compound 1.

[0542] Evaluation Example 3

[0543] The luminance was measured by using a current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) (at 500 candela / m², cd / m 2 The driving voltage, external quantum efficiency, and lifetime of the organic light emitting devices according to Examples 1 to 13 and Comparative Examples AC were measured (Table 5). 95 ) represents the amount of time (hours, h) that has elapsed when the brightness is 95% of the initial brightness (100%). The lifespan (T 95 )(at 500cd / m 2 The data below are the lifespan (T 95 ) is expressed as a relative value (%).

[0544] [Table 5]

[0545]

[0546]

[0547]

[0548]

[0549] Referring to Table 5, it was confirmed that the organic light-emitting devices of Examples 1 to 13 had excellent driving voltage, external quantum efficiency, and / or lifespan characteristics compared to those of the organic light-emitting devices of Comparative Examples AC.

[0550] The condensed ring compound may have excellent delayed fluorescence emission characteristics, and the organic light emitting device including the condensed ring compound may have high efficiency and / or a long lifespan.

[0551] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects in each embodiment should typically be considered as available for other similar features or aspects in other embodiments.

[0552] Although one or more embodiments have been described with reference to the drawings, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the description as defined by the following claims.

Claims

1. A fused ring compound represented by Formula 1: Formula 1 in D1 is represented by one selected from Formulas 2-1 and 2-2, and A1 is represented by one selected from Formulas 3-14 and 3-17: in, In Formulas 1, 2-1, 2-2, 3-14, and 3-17, R 11 and R 12 Each independently selected from: Phenyl and biphenyl; and Phenyl and biphenyl, each substituted by at least one selected from the group consisting of deuterium, C1-C 20 Alkyl, and C1-C 20 Alkoxy, R 13 and R 14 are each independently selected from hydrogen and deuterium, In formula 2-1 is a group represented by Formula 9-11, wherein in Formula 9-11, b21 is 1, R 21 C1-C 20 Alkyl, phenyl, or C1-C 20 Alkyl-substituted phenyl, and in formula 2-1 is a group represented by Formula 9-11, wherein in Formula 9-11, b21 is 1, R 21 C1-C 20 Alkyl, phenyl, or C1-C 20 an alkyl-substituted phenyl group, or In formula 2-1 is a group represented by Formula 9-11, wherein in Formula 9-11, b21 is 1, R 21 is a carbazolyl group, and in Formula 2-1 is a group represented by formula 9-11, wherein in formula 9-11, b21 is 4, and R 21 are each independently hydrogen or deuterium, In formula 2-2 is a group represented by formula 9-11, wherein in formula 9-11, b21 is 4, and R 21 are each independently hydrogen or deuterium, and in Formula 2-2 is a group represented by formula 9-21 or 9-32, In formula 9-21, b22a is 2, b22b is 4, and R 22a and R 22b are independently hydrogen, deuterium, C1-C 20 Alkyl, or C1-C 20 Alkoxy, X 91 Selected from O, S, and N(R 22d ), R 22d is phenyl or C1-C 20 Alkyl-substituted phenyl, In formula 9-32, b22a is 2, b22b is 2, b22c is 4, R 22a to R 22c are independently hydrogen, deuterium, C1-C 20 Alkyl, or C1-C 20 Alkoxy, X 91 is selected from O and S, and X 92 N(R 22d ), R 22d is phenyl or C1-C 20 Alkyl-substituted phenyl, C1-C4 in formulas 2-1, 2-2, 9-11, 9-21 and 9-32 are each independently a carbon atom, R 32 and R 34 Each independently selected from: Phenyl, biphenyl, and terphenyl; and Phenyl, biphenyl, and terphenyl, each substituted by at least one selected from the group consisting of deuterium, C1-C 20 Alkyl, and C1-C 20 Alkoxy, R 35 is hydrogen, deuterium, methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, and hexyl, and * indicates the binding site with the adjacent atom.

2. The fused ring compound according to claim 1, wherein R 11 and R 12 Each independently selected from: Phenyl and biphenyl; and Phenyl and biphenyl groups, each of which is at least one substituted group selected from the group consisting of deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, methoxy, ethoxy, propoxy, butoxy, and pentoxy.

3. The fused ring compound according to claim 1, wherein The fused ring compound represented by Formula 1 is represented by Formula 1-1: Formula 1-1 in, In formula 1-1, D1, A1, R 11 , and R 12 are independently the same as in Formula 1.

4. The fused ring compound according to claim 1, wherein The fused ring compound represented by Formula 1 is selected from the following compounds:

5. Organic light-emitting devices, including: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer includes an emission layer, and The organic layer comprises at least one fused-cyclic compound according to any one of claims 1 to 4. The organic light emitting device according to claim 5 , wherein The first electrode is an anode, The second electrode is a cathode, The organic layer further includes a hole transport region disposed between the first electrode and the emission layer and an electron transport region disposed between the emission layer and the second electrode, wherein the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

7. The organic light emitting device according to claim 5, wherein The emission layer includes the condensed-cyclic compound.

8. The organic light emitting device according to claim 7, wherein The ratio of the fluorescent emission component emitted from the emission layer to the total emission component is 90% or more.

9. The organic light emitting device according to claim 7, wherein The fused ring compound is a fluorescent emitter, and A ratio of an emission component emitted from the condensed-cyclic compound to a total emission component emitted from the emission layer is 80% or more.

10. The organic light emitting device according to claim 9, wherein The emission layer is composed of the condensed ring compound; or The emitting layer further includes a body.

11. The organic light emitting device according to claim 7, wherein The emission layer includes a host and a dopant, The host includes the fused ring compound, The amount of the host is greater than the amount of the dopant, and A ratio of an emission component of the dopant to a total emission component emitted from the emission layer is 80% or more.

12. The organic light emitting device according to claim 7, wherein The emission layer includes a host, an auxiliary dopant, and a main dopant, The auxiliary dopant includes the condensed ring compound, and A ratio of an emission component of the main dopant to a total emission component emitted from the emission layer is 80% or more.

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