阅读说明：本技术 稠环化合物和包括其的有机发光器件 (Condensed ring compound and organic light emitting device including the same ) 是由 郑妍淑 田顺玉 沼田真树 沈明善 李河燮 印守康 于 2019-02-01 设计创作，主要内容包括：公开稠环化合物和包括其的有机发光器件。所述稠环化合物由式1表示,其中,在式1中,A<Sub>1</Sub>、D<Sub>1</Sub>、和R<Sub>11</Sub>-R<Sub>14</Sub>与说明书中描述的相同。式1<Image he="380" wi="450" file="DDA0001967728330000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>(Disclosed are a fused ring compound and an organic light emitting device including the same. The condensed ring compound is represented by formula 1, wherein, in formula 1, A 1 、D 1 And R 11 ‑R 14 As described in the specification. Formula 1)

1. A fused ring compound represented by formula 1:

formula 1

Formula 2

Wherein, in formulae 1, 2, and 3-1 to 3-5,

D₁is a group represented by the formula 2,

A₁is a group represented by one selected from the group consisting of formulas 3-1 to 3-5,

R₁₁and R₁₂Each independently is substituted or unsubstituted C₆-C₃₀An aryl group, a heteroaryl group,

A₂₁and A₂₂Each independently selected from the group consisting of a phenyl group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, an indolofluorene group, an indolocarbazole group, an indenofluorene group, an indenocarbazole group, an indenodibenzofuran group, an indenodibenzothiophene group, a benzofurofluorene group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienodibenzothiophene group, a benzothienocarbazole group, a benzothienodibenzofuran group, and a benzothienodibenzothiophene group,

X₃₁is N or C (R)₃₁)；X₃₂Is N or C (R)₃₂)；X₃₃Is N or C (R)₃₃)；X₃₄Is N or C (R)₃₄)；X₃₅Is N or C (R)₃₅)；X₃₆Is N or C (R)₃₆)；X₃₇Is N or C (R)₃₇) (ii) a And X₃₈Is N or C (R)₃₈) Wherein X is selected from the group consisting of those in the formula 3-1₃₁-X₃₅At least one of (A) is N, and is selected from X in formulae 3-2 to 3-5₃₆-X₃₈At least one of (a) is N,

Y₃₁is selected from the group consisting of O and S,

R₁₃、R₁₄、R₂₁、R₂₂and R₃₁-R₃₉Each independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, and substituted or unsubstituted C₁-C₆₀Alkyl, substituted or unsubstituted C₂-C₆₀Alkenyl, substituted or unsubstituted C₂-C₆₀Alkynyl, substituted or unsubstituted C₁-C₆₀Alkoxy, substituted or unsubstituted C₃-C₁₀Cycloalkyl, substituted or unsubstituted C₁-C₁₀Heterocycloalkyl, substituted or unsubstituted C₃-C₁₀Cycloalkenyl, substituted or unsubstituted C₁-C₁₀Heterocycloalkenyl, substituted or unsubstituted C₆-C₆₀Aryl, substituted or unsubstituted C₆-C₆₀Aryloxy, substituted or unsubstituted C₆-C₆₀Arylthio, substituted or unsubstituted C₇-C₆₀Aralkyl, substituted or unsubstituted C₁-C₆₀Heteroaryl, substituted or unsubstituted C₁-C₆₀Heteroaryloxy, substituted or unsubstituted C₁-C₆₀Heteroarylthio, substituted or unsubstituted C₂-C₆₀Heteroaralkyl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si (Q)₁)(Q₂)(Q₃)、-N(Q₄)(Q₅) and-B (Q)₆)(Q₇)，

Is selected from R₃₁-R₃₉Optionally joined to form a fused ring,

b21 and b22 are each independently selected from 1, 2,3, 4,5, 6, 7, and 8,

b39 is selected from 1, 2,3, and 4,

Q₁-Q₇each independently selected from hydrogen and C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl, C₁-C₆₀Alkoxy radical, C₃-C₁₀Cycloalkyl radical, C₁-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₁-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₁-C₆₀A heteroaryl group, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heteropolycyclic group, and

denotes the binding site to the adjacent atom.

2. The fused ring compound of claim 1, wherein

R₁₁And R₁₂Each independently selected from:

phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracyl, benzo [9,10 ]]Phenanthryl, pyrenyl, and

phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracenyl, benzo [9,10 ] substituted by at least one member selected from the group consisting of]Phenanthryl, pyrenyl, and

3. The fused ring compound of claim 1, wherein

R₁₁And R₁₂Each independently selected from:

phenyl, biphenyl, terphenyl, and naphthyl; and

phenyl, biphenyl, terphenyl, and naphthyl, each substituted with at least one substituent 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.

4. The fused ring compound of claim 1, wherein

A₂₁Is a phenyl group, and

A₂₂selected from the group consisting of phenyl groups, fluorene groups, carbazole groups, dibenzofuran groups, dibenzothiophene groups, indolofluorene groups, indolocarbazole groups, indenofluorene groups, indenocarbazole groups, indenodibenzofuran groups, indenodibenzothiophene groups, benzofuranofluorene groups, benzofuranocarbazole groups, benzofuranodibenzofuran groupsA pyran group, a benzofurodibenzothiophene group, a benzothienofluorene group, a benzothienocarbazole group, a benzothienodibenzofuran group, and a benzothienodibenzothiophene group.

5. The fused ring compound of claim 1, wherein

X selected from the group consisting of those in the formula 3-1₃₁-X₃₅Two or three of (A) are each independently N and selected from X in formulae 3-2 to 3-5₃₆-X₃₈Are each independently N.

6. The fused ring compound of claim 1, wherein

R₁₃And R₁₄Each independently selected from:

hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, and

phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracenyl, benzo [9,10 ] substituted by at least one member selected from the group consisting of]Phenanthryl, pyrenyl, and

7. The fused ring compound of claim 1, wherein

R₂₁And R₂₂Each independently selected from:

hydrogen, deuterium, C₁-C₂₀Alkyl radical, C₁-C₂₀Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, cyclopentadienyl, phenyl, biphenyl, and naphthyl,

c each substituted by at least one member selected from the group consisting of₁-C₂₀Alkyl radical, C₁-C₂₀Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, cyclopentadienyl, phenyl, biphenyl, and naphthyl,

8. The fused ring compound of claim 1, wherein

D₁Represented by one selected from formulas 2-1 and 2-2:

wherein, in the formulae 2-1, 2-2, 9-11, 9-21 to 9-23, and 9-31 to 9-48,

A₂₁are groups represented by the formulae 9 to 11,

A₂₂selected from the group represented by the formulae 9-11, 9-21 to 9-23, and 9-31 to 9-48,

C₁-C₄each of which is independently a carbon atom,

R₂₁、R₂₂、b₂₁and b₂₂Each independently the same as in formula 2,

X₉₁selected from O, S, N (R)_22d) And C (R)_22d)(R₂₂e)，

X₉₂Selected from O, S, N (R)₂₂f) And C (R)₂₂f)(R_22g)，

R_22a-R_22gEach independently of the other with respect to R in formula 2₂₂Are the same as described, and

b22a-b22c are each independently the same as described for b22 in formula 2.

9. The fused ring compound of claim 1, wherein

A₁Represented by one selected from formulas 3-11 to 3-35:

wherein, in formulae 3-11 to 3-35,

Y₃₁、R₃₁-R₃₉and b39 are each independently the same as in formulae 3-1 to 3-5, and

denotes the binding site to the adjacent atom.

10. The fused ring compound of claim 1, wherein

The fused ring compound represented by formula 1 is represented by formula 1-1:

formula 1-1

Wherein, in the formula 1-1,

D₁、A₁、R₁₁and R₁₂Each independently is the same as in formula 1.

11. The fused ring compound of claim 10 wherein

D₁From the group of formula 2One of the representations of-1 and 2-2, and

A₁represented by one selected from formulas 3-11 to 3-35:

wherein, in formulae 2-1, 2-2, 9-11, 9-21 to 9-23, 9-31 to 9-48, and 3-11 to 3-35,

A₂₁are groups represented by the formulae 9 to 11,

A₂₂selected from the group represented by the formulae 9-11, 9-21 to 9-23, and 9-31 to 9-48,

C₁-C₄each of which is independently a carbon atom,

R₂₁、R₂₂、b₂₁and b₂₂Each independently the same as in formula 2,

X₉₁selected from O, S, N (R)_22d) And C (R)_22d)(R_22e)，

X₉₂Selected from O, S, N (R)_22f) And C (R)_22f)(R_22g)，

R_22a-R_22gEach independently of the other with respect to R in formula 2₂₂The same as that described above is true for the description,

b22a-b22c are each independently the same as described for b22 in formula 2,

Y₃₁、R₃₁-R₃₉and b39 are each independently the same as described with respect to formulas 3-1 to 3-5, and

denotes the binding site to the adjacent atom.

12. The fused ring compound of claim 1, wherein

The fused ring compound represented by formula 1 is selected from compounds 1 to 1030:

13. an organic light emitting device comprising:

a first electrode;

a second electrode; and

an organic layer disposed between the first electrode and the second electrode,

wherein the organic layer comprises an emissive layer, and

wherein the organic layer comprises at least one fused ring compound as recited in any one of claims 1-12.

14. An organic light emissive device according to claim 13, wherein

The first electrode is an anode and the second electrode is a cathode,

the second electrode is a cathode and 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

wherein the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

15. An organic light emissive device according to claim 13, wherein

The emission layer includes the fused ring compound.

16. An organic light emissive device according to claim 15, wherein

A ratio of a fluorescence emission component emitted from the emission layer to a total emission component is 90% or more.

17. An organic light emissive device according to claim 15, 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.

18. An organic light emissive device according to claim 17, wherein

The emitting layer is composed of the condensed ring compound; or

The emissive layer further comprises a body.

19. An organic light emissive device according to claim 15, wherein

The emissive layer includes a host and a dopant,

the body 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.

20. An organic light emissive device according to claim 15, wherein

The emission layer includes a host, an auxiliary dopant, and a main dopant,

the auxiliary dopant includes the fused 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.

Technical Field

One or more embodiments relate to a fused ring compound and an organic light emitting device including the same.

Background

Organic Light Emitting Devices (OLEDs) are self-emissive devices that produce full-color images and also have wide viewing angles, high contrast, short response times, and excellent characteristics in terms of luminance, driving voltage, and response speed, compared to other types of devices.

In an example, 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 supplied from the anode may move toward the emission layer through the hole transport region, and electrons supplied from the cathode may move toward the emission layer through the electron transport region. Carriers such as holes and electrons recombine in the emission layer to generate excitons. These excitons transition from an excited state to a ground state, thereby generating light.

Various types of organic light emitting devices are known. However, there is still a need for OLEDs having low driving voltages, high efficiency, high brightness, and long lifetimes.

Disclosure of Invention

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 lifetime.

Additional aspects will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the embodiments provided.

One aspect provides a fused ring compound represented by formula 1:

formula 1

Formula 2

In formulae 1, 2, and 3-1 to 3-5,

D₁may be a group represented by formula 2,

A₁may be a group represented by one selected from the group consisting of formulas 3-1 to 3-5,

R₁₁and R₁₂Each independently may be substituted or unsubstituted C₆-C₃₀An aryl group, a heteroaryl group,

A₂₁and A₂₂Each of which is 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 indenofluorene group, an indenocarbazole group, an indenodibenzofuran group, an indenodibenzothiophene group, a benzofurofluorene group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienodibenzothiophene group, a benzothienocarbazole group, a benzothienodibenzofuran group, and a benzothienodibenzothiophene group,

X₃₁can be N or C (R)₃₁)；X₃₂Can be N or C (R)₃₂)；X₃₃Can be N or C (R)₃₃)；X₃₄Can be N or C (R)₃₄)；X₃₅Can be N or C (R)₃₅)；X₃₆Can be N or C (R)₃₆)；X₃₇Can be N or C (R)₃₇) (ii) a And X₃₈Can be N or C (R)₃₈) Wherein X is selected from the group consisting of those in the formula 3-1₃₁-X₃₅At least one of (A) and (B) may be N, and is selected from X in formulae 3-2 to 3-5₃₆-X₃₈At least one of (a) may be N,

Y₃₁can be selected from the group consisting of O and S,

R₁₃、R₁₄、R₂₁、R₂₂and R₃₁-R₃₉Can be independently selected from hydrogen, deuterium, -F, -Cl and-Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C₁-C₆₀Alkyl, substituted or unsubstituted C₂-C₆₀Alkenyl, substituted or unsubstituted C₂-C₆₀Alkynyl, substituted or unsubstituted C₁-C₆₀Alkoxy, substituted or unsubstituted C₃-C₁₀Cycloalkyl, substituted or unsubstituted C₁-C₁₀Heterocycloalkyl, substituted or unsubstituted C₃-C₁₀Cycloalkenyl, substituted or unsubstituted C₁-C₁₀Heterocycloalkenyl, substituted or unsubstituted C₆-C₆₀Aryl, substituted or unsubstituted C₆-C₆₀Aryloxy, substituted or unsubstituted C₆-C₆₀Arylthio, substituted or unsubstituted C₇-C₆₀Aralkyl, substituted or unsubstituted C₁-C₆₀Heteroaryl, substituted or unsubstituted C₁-C₆₀Heteroaryloxy, substituted or unsubstituted C₁-C₆₀Heteroarylthio, substituted or unsubstituted C₂-C₆₀Heteroaralkyl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si (Q)₁)(Q₂)(Q₃)、-N(Q₄)(Q₅) and-B (Q)₆)(Q₇)，

Is selected from R₃₁-R₃₉May optionally be joined to form a fused ring,

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

b39 may be selected from 1, 2,3, and 4,

Q₁-Q₇can be independently selected from hydrogen and C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl, C₁-C₆₀Alkoxy radical, C₃-C₁₀Cycloalkyl radical, C₁-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₁-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₁-C₆₀A heteroaryl group, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heteropolycyclic group, and

denotes the binding site to the adjacent atom.

Another aspect provides an organic light emitting device comprising:

a first electrode;

a second electrode; and

an organic layer disposed between the first electrode and the second electrode,

wherein the organic layer comprises an emissive layer, and

wherein the organic layer comprises at least one fused ring compound described above.

Drawings

These and/or other aspects will become apparent and more readily appreciated from the following description of embodiments, taken in conjunction with fig. 1, which is a schematic view of an organic light emitting device according to an embodiment.

Detailed Description

Reference will now be made in detail to the embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout. In this regard, the present embodiments may have different forms and should not be construed as limited to the descriptions set forth herein. Accordingly, the embodiments are described below only by referring to the 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 associated listed items. The expression "at least one of" when preceding or following a list of elements modifies the entire list of elements without modifying individual elements of the list.

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 be present. In contrast, when an element is referred to as being "directly on" another element, there are no intervening elements present.

It will be understood that, although the terms first, second, third, etc. may be used herein to describe various elements, components, regions, layers and/or sections, these elements, components, regions, layers and/or sections should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer or section from another element, component, region, layer or section. Thus, a first element, component, region, layer or section discussed below could be termed a second element, component, region, layer or section without departing from the teachings of the present embodiments.

The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise.

The term "or" means "and/or". It will be further understood that the terms "comprises" and/or "comprising," when used in this specification, specify 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 other features, regions, integers, steps, operations, elements, components, and/or groups thereof.

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 that is 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 expressly so defined herein.

Exemplary embodiments are described herein with reference to cross-sectional views that are schematic illustrations of idealized embodiments. As such, deviations from the shapes of the figures as a result, for example, of manufacturing techniques and/or tolerances, are to be expected. Thus, the embodiments described herein should not be construed as limited to the particular shapes of regions as illustrated herein but are to include deviations in shapes that result, for example, from manufacturing. For example, regions illustrated or described as flat may typically have rough and/or non-linear features. Further, the illustrated sharp corners 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 a region and are not intended to limit the scope of the present claims.

As used herein, "about" or "approximately" includes the stated value and is meant to be within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art in view of the measurement in question and the error associated with measurement of the particular quantity (i.e., limitations of the measurement system). For example, "about" may mean a deviation from the stated value in one or more deviation ranges, or in a range of ± 10% or 5%.

One aspect of the present disclosure provides a fused ring compound represented by formula 1, wherein D in formula 1₁May be a group represented by formula 2, and A in formula 1₁May be a group represented by one selected from formulas 3-1 to 3-5:

formula 1

Formula 2

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

R in formula 1₁₁And R₁₂Each independently may be substituted or unsubstituted C₆-C₃₀And (4) an aryl group.

In one embodiment, formulaR in 1₁₁And R₁₂May each be independently selected from:

phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracyl, benzo [9,10 ]]Phenanthryl, pyrenyl, and

a group; and

phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracenyl, benzo [9,10 ] substituted by at least one member selected from the group consisting of]Phenanthryl, pyrenyl, andbase: deuterium, -F, -Cl, -Br, -I, cyano, C₁-C₂₀Alkyl radical, C₁-C₂₀Alkoxy, and phenyl, but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, R in formula 1₁₁And R₁₂May each be independently selected from:

phenyl, biphenyl, terphenyl, and naphthyl; and

phenyl, biphenyl, terphenyl, and naphthyl, each substituted with at least one substituent 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, although embodiments of the present disclosure are not so limited.

In one or more embodiments, R in formula 1₁₁And R₁₂May each be independently selected from:

a phenyl group; and

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

A in formula 2₂₁And A₂₂Can be independently selected from phenyl group, fluorene group, carbazole group, and diphenyl groupAn benzofuran group, a dibenzothiophene group, an indolofluorene group, an indolocarbazole group, an indenofluorene group, an indenocarbazole group, an indenodibenzofuran group, an indenodibenzothiophene group, a benzofurofluorene group, a benzofurocarbazole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienofluorene group, a benzothienocarbazole group, a benzothienodibenzofuran group, and a benzothienodibenzothiophene group.

In one embodiment, in formula 2,

A₂₁it may be a phenyl group or a substituted phenyl group,

A₂₂may be selected from the group consisting of a phenyl group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, an indolofluorene group, an indolocarbazole group, an indenofluorene group, an indenocarbazole group, an indenodibenzofuran group, an indenodibenzothiophene group, a benzofurofluorene group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienodibenzothiophene group, a benzothienodibenzofuran group, and a benzothienodibenzothiophene group, although embodiments of the present disclosure are not limited thereto.

In formulae 3-1 to 3-5, X₃₁Can be N or C (R)₃₁)；X₃₂Can be N or C (R)₃₂)；X₃₃Can be N or C (R)₃₃)；X₃₄Can be N or C (R)₃₄)；X₃₅Can be N or C (R)₃₅)；X₃₆Can be N or C (R)₃₆)；X₃₇Can be N or C (R)₃₇) (ii) a And X₃₈Can be N or C (R)₃₈) Wherein X is selected from the group consisting of those in the formula 3-1₃₁-X₃₅At least one of (A) and (B) may each independently be N and is selected from X in formulae 3-2 to 3-5₃₆-X₃₈May each independently be N.

In one embodiment, X is selected from those in formula 3-1₃₁-X₃₅Two or three of (A) may each independently be N, and is selected from X in formulae 3-2 to 3-5₃₆-X₃₈May each be independently N, but embodiments of the present disclosure are not limited thereto.

In formulae 3-2 to 3-5, Y₃₁Can be selected from O and S.

In formulae 1, 2, and 3-1 to 3-5, R₁₃、R₁₄、R₂₁、R₂₂And R₃₁-R₃₉Each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, and substituted or unsubstituted C₁-C₆₀Alkyl, substituted or unsubstituted C₂-C₆₀Alkenyl, substituted or unsubstituted C₂-C₆₀Alkynyl, substituted or unsubstituted C₁-C₆₀Alkoxy, substituted or unsubstituted C₃-C₁₀Cycloalkyl, substituted or unsubstituted C₁-C₁₀Heterocycloalkyl, substituted or unsubstituted C₃-C₁₀Cycloalkenyl, substituted or unsubstituted C₁-C₁₀Heterocycloalkenyl, substituted or unsubstituted C₆-C₆₀Aryl, substituted or unsubstituted C₆-C₆₀Aryloxy, substituted or unsubstituted C₆-C₆₀Arylthio, substituted or unsubstituted C₇-C₆₀Aralkyl, substituted or unsubstituted C₁-C₆₀Heteroaryl, substituted or unsubstituted C₁-C₆₀Heteroaryloxy, substituted or unsubstituted C₁-C₆₀Heteroarylthio, substituted or unsubstituted C₂-C₆₀Heteroaralkyl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si (Q)₁)(Q₂)(Q₃)、-N(Q₄)(Q₅) and-B (Q)₆)(Q₇)，

Is selected from R₃₁-R₃₉Two adjacent groups of (a) may optionally be linked to each other to form a fused ring, and

Q₁-Q₇can be independently selected from hydrogen and C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl, C₁-C₆₀Alkoxy radical, C₃-C₁₀Cycloalkyl radical, C₁-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₁-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₁-C₆₀A heteroaryl group, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heteropolycyclic group.

In one embodiment, in formula 1, R₁₃And R₁₄May each be independently selected from:

hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, and

a group; and

phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracenyl, benzo [9,10 ] substituted by at least one member selected from the group consisting of]Phenanthryl, pyrenyl, and

base: deuterium, -F, -Cl, -Br, -I, cyano, C₁-C₂₀Alkyl radical, C₁-C₂₀Alkoxy, and phenyl, but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, R in formula 1₁₃And R₁₄May each be independently selected from:

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

phenyl, biphenyl, terphenyl, and naphthyl, each substituted with at least one substituent 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, although embodiments of the present disclosure are not so limited.

In one or more embodiments, R in formula 1₁₃And R₁₄May be hydrogen, but embodiments of the present disclosure are not limited thereto.

In one embodiment, R in formula 2₂₁And R₂₂Can be independently selected from hydrogen, deuterium, cyano, C₁-C₂₀Alkyl radical, C₁-C₂₀Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenaphthenyl, acenaphthenyl, fluorenyl, spiro-dibenzofluorenyl, benzofluorenyl, dibenzofluorenyl, phenaenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo [9,10 ] benzo]Phenanthryl, pyrenyl,

A group selected from the group consisting of a phenyl group, a tetracenyl group, a picenyl group, a perylene group, a pentylene group, a hexacenyl group, a pentacenyl group, a rubicene group, a coronene group, an egg phenyl group, a pyrrolyl group, a furyl group, a thienyl group, an indolyl group, a benzofuryl group, a benzothienyl group, a carbazolyl group, a dibenzofuryl group, a dibenzothienyl group, a benzocarbazolyl group, a naphthobenzofuryl group, a naphthobenzothienyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, an indolocarbazolyl group, an indodibenzofuryl group, and an indolophthalylbenzothienyl group; and

c each substituted by at least one member selected from the group consisting of₁-C₂₀Alkyl radical, C₁-C₂₀Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenaphthenyl, acenaphthenyl, fluorenyl, spiro-dibenzofluorenyl, benzofluorenyl, dibenzofluorenyl, phenaenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo [9,10 ] benzo]Phenanthryl, pyrenyl,

A group selected from the group consisting of a phenyl group, a tetracenyl group, a picenyl group, a perylene group, a pentylene group, a hexacenyl group, a pentacenyl group, a rubicene group, a coronene group, an egg phenyl group, a pyrrolyl group, a furyl group, a thienyl group, an indolyl group, a benzofuryl group, a benzothienyl group, a carbazolyl group, a dibenzofuryl group, a dibenzothienyl group, a benzocarbazolyl group, a naphthobenzofuryl group, a naphthobenzothienyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, an indolocarbazolyl group, an indodibenzofuryl group, and an indolophthalylbenzothienyl group: deuterium, C₁-C₂₀Alkyl radical, C₁-C₂₀Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, phenylcarbazolyl, biphenylcarbazolyl, dibenzofuranyl, and dibenzothiophenyl, although embodiments of the present disclosure are not limited thereto.

In one or more embodiments, R in formula 2₂₁And R₂₂May each be independently selected from:

hydrogen, deuterium, cyano, C₁-C₂₀Alkyl radical, C₁-C₂₀Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, phenylcarbazolyl, biphenylcarbazolyl, dibenzofuranyl, and dibenzothiophenyl; and

at least one substituted phenyl and carbazolyl group each selected from the group consisting of: cyano radicals, C₁-C₂₀Alkyl groups, and phenyl groups, but embodiments of the present disclosure are not limited thereto.

In one embodiment, R in formulas 3-1 to 3-5₃₁-R₃₉May each be independently selected from:

hydrogen, phenyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, azabenzofuranyl, azabenzothiophenyl, diazabenzodibenzofuranyl, and diazabenzophenyl; and

phenyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, bis substituted with at least one substituent each selected fromBenzothienyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, azabicyclofuranyl, azabicycloheptanenyl, diaza dibenzofuranyl, and diaza dibenzothienyl: deuterium, -F, -Cl, -Br, -I, cyano, C₁-C₂₀Alkyl radical, C₁-C₂₀Alkoxy, and phenyl, but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, R in formulas 3-1 through 3-5₃₁-R₃₉May each be independently selected from:

hydrogen, phenyl, biphenyl, terphenyl, dibenzofuranyl, dibenzothienyl, pyridyl, azabiphenyl, diaza dibenzofuranyl, and diaza dibenzothienyl; and

phenyl, biphenyl, terphenyl, dibenzofuranyl, dibenzothienyl, azabiphenyl, diaza dibenzothienyl, and diaza dibenzothienyl, each substituted with a phenyl group, although embodiments of the present disclosure are not limited thereto.

For example, D in formula 1₁May be represented by one selected from formulas 2-1 and 2-2, but the embodiments of the present disclosure are not limited thereto:

in formulae 2-1, 2-2, 9-11, 9-21 to 9-23, and 9-31 to 9-48,

A₂₁may be a group represented by the formula 9 to 11,

A₂₂may be a group represented by one selected from the group consisting of formulas 9-11, 9-21 to 9-23, and 9-31 to 9-48,

C₁-C₄may each independently be a carbon atom,

R₂₁、R₂₂、b₂₁and b₂₂May be each independently the same as in formula 2,

X₉₁can be selected from O, S, N (R)_22d) And C (R)_22d)(R_22e)，

X₉₂Can be selected from O, S, N (R)_22f) And C (R)_22f)(R_22g)，

R_22a-R_22gMay each independently have R in the formula 2₂₂Is defined the same as that of (A), and

b22a-b22c may each independently have the same definition as b22 in formula 2.

For example, A in formula 1₁May be represented by one selected from formulas 3-11 to 3-35, but the embodiments of the present disclosure are not limited thereto:

in formulae 3-11 to 3-35,

Y₃₁、R₃₁-R₃₉and b39 may each independently have the same definitions as those of formulae 3-1 to 3-5, and

denotes the binding site to the adjacent atom.

In one embodiment, A in formula 1₁May be represented by one selected from formulae 3-14, 3-15, 3-17, 3-21, 3-25, 3-29, 3-33, 3-34, and 3-35, but the embodiment of the present disclosure is not limited thereto.

For example, the fused ring compound represented by formula 1 may be represented by formula 1-1, but embodiments of the present disclosure are not limited thereto:

formula 1-1

In the formula 1-1, the compound represented by the formula,

D₁、A₁、R₁₁and R₁₂May each independently have the same definitions as those in formula 1.

In one embodiment, in formula 1-1,

D₁may be represented by one selected from the group consisting of formulas 2-1 and 2-2,

A₁may be represented by one selected from the group consisting of formulas 3-11 to 3-35, and

R₁₁and R₁₂May each independently have the same definitions as those in formula 1:

in formulae 2-1, 2-2, 9-11, 9-21 to 9-23, 9-31 to 9-48, and 3-11 to 3-35,

A₂₁may be a group represented by the formula 9 to 11,

A₂₂may be a group represented by one selected from the group consisting of formulas 9-11, 9-21 to 9-23, and 9-31 to 9-48,

C₁-C₄may each independently be a carbon atom,

R₂₁、R₂₂、b₂₁and b₂₂May be each independently the same as in formula 2,

X₉₁can be selected from O, S, N (R)_22d) And C (R)_22d)(R_22e)，

X₉₂Can be selected from O, S, N (R)_22f) And C (R)_22f)(R_22g)，

R_22a-R_22gMay each independently have R in the formula 2₂₂Are defined in the same way as in (a),

b22a-b22c may each independently have the same definition as b22 in formula 2,

Y₃₁、R₃₁-R₃₉and b39 may each independently have the same definitions as those described in formulas 3-1 to 3-5, and

denotes the binding site to the adjacent atom.

In one embodiment, the condensed-ring compound represented by formula 1 may be selected from compounds 1 to 1030, but embodiments of the present disclosure are not limited thereto:

the fused ring compound represented by formula 1 may include a group (A) represented by one selected from formulas 3-1 to 3-5 and capable of serving as an electron acceptor group₁) And a group (D) represented by formula 2 and capable of serving as an electron donor group₁). Thus, in the fused ring compound represented by formula 1, HOMO and LUMO may be spatially separated from each other, and thus Δ E_ST(at the lowest excited singlet energy level (E)_S1) And lowest excited triplet energy level (E)_T1) The difference therebetween) can be reduced. Therefore, the fused ring compound represented by formula 1 may cause reverse intersystem crossing (RISC) even at low temperatures (e.g., room temperature).

R in formula 1₁₁And R₁₂Is substituted or unsubstituted C₆-C₃₀And (4) an aryl group. Thus, the compound represented by formula 1 includes D₁And comprises A₁Is increased (i.e., includes D)₁And comprises A₁Planar twist) of the fused ring compound, the difference between the lowest excited singlet level and the lowest excited triplet level of the fused ring compound represented by formula 1 can be reduced. Accordingly, the fused ring compound represented by formula 1 may have high RISC efficiency, so that an electronic device, such as an organic light emitting device, including the fused ring compound may have high efficiency and/or long lifetime.

The fused ring compound represented by formula 1 may satisfy the following equation 1:

equation 1

0eV<ΔE_ST≤0.5eV。

In the case of the equation 1, the,

ΔE_STis at the lowest excited singlet energy level (E) of the fused ring compound represented by formula 1_S1) And minimum excitation of the fused ring compound represented by formula 1Triplet energy level (E)_T1) The difference between them. E_T1And E_S1Was evaluated by the DFT method using a Gaussian program with structure optimization at the level of B3LYP/6-31G (d, p).

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:

equation 1-1

0.01eV<ΔE_ST≤0.3eV。

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

In addition, D in the fused ring compound represented by formula 1₁And A₁May be attached at the "para" position of the phenylene group. Therefore, the condensed ring compound represented by formula 1 has high oscillator strength, and an electronic device such as an organic light emitting device including the condensed ring compound may have high light emitting efficiency.

For example, some compounds were evaluated for HOMO, LUMO, and T levels by the DFT method using a Gaussian program (structurally optimized at the level of B3LYP/6-31G (d, p))₁Energy level, S₁Energy level, and oscillator strength, and the results thereof are shown in table 1.

TABLE 1

Referring to table 1, it was confirmed that the fused ring compound represented by formula 1 had a small difference between the singlet level and the triplet level and a large oscillator strength. Therefore, an electronic device, such as an organic light-emitting device, including the fused ring compound represented by formula 1 may have high light-emitting efficiency.

The synthetic method of the fused ring compound represented by formula 1 may be recognized by one of ordinary skill in the art by referring to the synthetic examples provided below.

The fused ring compound of formula 1 is useful as a material for electronic devices such as organic light emitting devices. According to another aspect of the exemplary embodiments, an organic light emitting device includes: 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 at least one of the above-described fused ring compounds represented by formula 1.

The organic light emitting device may have a low driving voltage, high efficiency, high luminance, high quantum emission efficiency, and a long lifetime due to the inclusion of the organic layer including the fused ring compound represented by formula 1.

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

The emission layer of the organic light emitting device may be implemented according to embodiment mode 1, 2, or 3 depending on the use of the fused ring compound represented by formula 1.