KR20220105577A - Organic electroluminescence device and polycyclic compound for organic electroluminescence device - Google Patents

Abstract

The organic electroluminescent device of one embodiment includes: a first electrode; a hole transport region disposed on the first electrode; a light emitting layer disposed on the hole transport region; an electron transport region disposed on the light emitting layer, and a second electrode disposed on the electron transport region. The light emitting layer includes a polycyclic compound represented by chemical formula, thereby, exhibiting high light emitting efficiency.

Description

Polycyclic compound for organic electroluminescent device and organic electroluminescent device

Polycyclic compound for organic electroluminescent device and organic electroluminescent device

Recently, as an image display device, an organic electroluminescence display has been actively developed. An organic electroluminescent display device is different from a liquid crystal display device, and by recombination of holes and electrons injected from the first electrode and the second electrode in the light emitting layer, the light emitting material containing the organic compound is emitted in the light emitting layer to realize display. It is a so-called self-luminous type display device.

In the application of organic electroluminescent devices to display devices, low driving voltage, high luminous efficiency, and long lifespan of the organic electroluminescent devices are required, and the development of materials for organic electroluminescent devices that can stably implement them is continuously required. have.

An object of the present invention is to provide a polycyclic compound for an organic electroluminescent device and an organic electroluminescent device, and more specifically, to provide a polycyclic compound included in a light emitting layer of an organic electroluminescent device and an organic electroluminescent device with high efficiency The purpose.

In one embodiment, a polycyclic compound represented by the following Chemical Formula 1 is provided.

[Formula 1]

In Formula 1, X ₁ to X ₂ are each independently O, S, or NR ₇ , e and f are each independently an integer of 0 or more and 4 or less, g is an integer of 0 or more and 2 or less, h is an integer of 0 or more and 3 or less, and R ₁ to R ₄ , R _5-1 to R _5-3 and R _6-1 to R _6-3 are each independently a hydrogen atom, a deuterium atom, a halogen atom, or a nitro group. , cyano group, hydroxyl group, substituted or unsubstituted amine group, substituted or unsubstituted thiol group, substituted or unsubstituted alkyl group having 1 or more and 20 or less carbon atoms, substituted or unsubstituted aryl group having 6 or more and 30 or less ring carbon atoms , a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring carbon atoms, or combine with an adjacent group to form a ring, and R ₇ is a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1 or more and 20 or less carbon atoms An alkyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, or combining with an adjacent group to form a ring, Y ₁ , and Y ₂ are each independently each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 6 or more and 20 or less carbon atoms, a substituted or unsubstituted aryl group having 6 or more and 30 or less ring carbon atoms, or a substituted or unsubstituted a cyclic heteroaryl group having 2 or more and 30 or less ring carbon atoms, provided that at least one of Y ₁ , and Y ₂ is a substituted or unsubstituted alkyl group having 6 or more and 20 or less carbon atoms, a substituted or unsubstituted ring carbon number of 6 or more an aryl group of 30 or less, or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring carbon atoms.

At least one of X ₁ and X ₂ is NR ₇ , R ₇ is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms can

Formula 1 may be represented by any one of Formulas 2-1 to 2-5 below.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

In Formulas 2-1 to 2-5, Ar _1-1 and Ar _1-2 are each independently a substituted or unsubstituted aryl group having 6 or more and 30 or less ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring carbon atoms, R ₁ to R ₄ , R _5-1 to R _5-3, R _6-1 to R _6-3 , Y ₁ , Y ₂ , and e to h are the same as defined in Formula 1 above.

The Ar _1-1 and Ar _1-2 may each independently be represented by any one of the following Chemical Formulas 5-1 to 5-3.

[Formula 5-1]

[Formula 5-2]

[Formula 5-3]

In Formulas 5-1 to 5-3,

R _a1 to R _a5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or an unsubstituted heteroaryl group having 2 or more and 30 or less carbon atoms, m1, m3, and m5 are each independently an integer of 0 or more and 5 or less, m2 is an integer of 0 or more and 9 or less, m4 is 0 or more and 3 or less is the integer of

The R _5-1 to R _5-3 , and At least one of R _6-1 to R _6-3 may be a substituted amine group.

Formula 1 may be represented by Formula 3-1 or Formula 3-2.

[Formula 3-1]

[Formula 3-2]

In Formulas 3-1 and 3-2, Ar _3-1, Ar _3-2 , Ar _4-1 and Ar _4-2 is each independently a substituted or unsubstituted aryl group having 6 or more and 30 or less ring carbon atoms, X ₁ , X ₂ , R ₁ to R ₄ , R _5-1 to R _5-3, R _{6- 1} to R _6-3 , Y ₁ , Y ₂ , and e to h are the same as defined in Formula 1 above.

Formula 1 may be represented by Formula 4 below.

[Formula 4]

In Formula 4, Ar _3-1, Ar _3-2 , Ar _4-1 and Ar _4-2 is each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, X ₁ , X ₂ , R ₁ to R ₄ , R _5-1 , R _5-3, R _{6- 1} , R _6-3 , Y ₁ , Y ₂ , and e to h are the same as defined in Formula 1.

Ar _3-1, Ar _3-2 , Ar _4-1 and Ar _4-2 may be each independently a substituted or unsubstituted aryl group having 6 or more and 18 or less ring carbon atoms.

The polycyclic compound represented by Formula 1 may be any one of the compounds shown in Compound Group 1 below.

In one embodiment, a first electrode, a hole transport region provided on the first electrode, a light emitting layer provided on the hole transport region, an electron transport region provided on the light emitting layer, and a second electrode provided on the electron transport region And, the light emitting layer provides an organic electroluminescent device comprising the polycyclic compound of an embodiment of the present invention.

The light emitting layer may emit delayed fluorescence.

The emission layer may be a delayed fluorescence emission layer including the first compound and the second compound, and the first compound may include the polycyclic compound.

The emission layer may be a thermally activated delayed fluorescence emission layer emitting light having a wavelength of 430 nm to 480 nm.

The organic electroluminescent device according to an embodiment of the present invention has excellent efficiency.

The polycyclic compound according to an embodiment of the present invention can be used as a material of the light emitting layer of the organic electroluminescent device, and by using the same, it is possible to improve the efficiency of the organic electroluminescent device.

1 is a plan view illustrating a display device according to an exemplary embodiment.
2 is a cross-sectional view illustrating a display device according to an exemplary embodiment.
3 is a cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present invention.
4 is a cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present invention.
5 is a cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present invention.
6 is a cross-sectional view schematically illustrating an organic electroluminescent device according to an embodiment of the present invention.
7 is a cross-sectional view illustrating a display device according to an exemplary embodiment.
8 is a cross-sectional view illustrating a display device according to an exemplary embodiment.

Since the present invention can have various changes and can have various forms, specific embodiments are illustrated in the drawings and described in detail in the text. However, this is not intended to limit the present invention to the specific disclosed form, it should be understood to include all modifications, equivalents and substitutes included in the spirit and scope of the present invention.

In describing each figure, like reference numerals have been used for like elements. In the accompanying drawings, the dimensions of the structures are enlarged than the actual size for clarity of the present invention. Terms such as first, second, etc. may be used to describe various elements, but the elements should not be limited by the terms. The above terms are used only for the purpose of distinguishing one component from another. For example, without departing from the scope of the present invention, a first component may be referred to as a second component, and similarly, a second component may also be referred to as a first component. The singular expression includes the plural expression unless the context clearly dictates otherwise.

In the present application, terms such as “comprise” or “have” are intended to designate that a feature, number, step, operation, component, part, or combination thereof described in the specification exists, but one or more other features It is to be understood that it does not preclude the possibility of the presence or addition of numbers, steps, operations, components, parts, or combinations thereof.

In the present application, when a part of a layer, film, region, plate, etc. is said to be “on” or “on” another part, this means not only when it is “directly on” another part, but also when there is another part in between. also includes Conversely, when a part of a layer, film, region, plate, etc. is said to be “under” or “under” another part, this includes not only cases where it is “directly under” another part, but also cases where another part is in between. . In addition, in the present application, “on” may include the case of being disposed not only on the upper part but also on the lower part.

As used herein, "substituted or unsubstituted" is a deuterium atom, a halogen atom, a cyano group, a nitro group, an amino group, a silyl group, an oxy group, a thio group, a sulfinyl group, a sulfonyl group, a carbonyl group, a boron group, a phosphine oxide It may mean unsubstituted or substituted with one or more substituents selected from the group consisting of a group, a phosphine sulfide group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, a hydrocarbon ring group, an aryl group, and a heterocyclic group. In addition, each of the substituents exemplified above may be substituted or unsubstituted. For example, a biphenyl group may be interpreted as an aryl group or a phenyl group substituted with a phenyl group.

In the present specification, "adjacent groups combine with each other to form a ring" may mean that adjacent groups combine with each other to form a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted hetero ring. Hydrocarbon rings include aliphatic hydrocarbon rings and aromatic hydrocarbon rings. Heterocycles include aliphatic heterocycles and aromatic heterocycles. The hydrocarbon ring and the hetero ring may be monocyclic or polycyclic. In addition, the rings formed by bonding to each other may be connected to other rings to form a spiro structure.

As used herein, "adjacent group" means a substituent substituted on an atom directly connected to the atom in which the substituent is substituted, another substituent substituted on the atom in which the substituent is substituted, or a substituent that is sterically closest to the substituent. can For example, two methyl groups in 1,2-dimethylbenzene can be interpreted as “adjacent groups” to each other, and 2 in 1,1-diethylcyclopentane The two ethyl groups can be interpreted as "adjacent groups" to each other. In addition, two methyl groups in 4,5-dimethylphenanthrene may be interpreted as “adjacent groups” to each other.

In the present specification, examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

In the present specification, the alkyl group may be linear, branched or cyclic. Carbon number of an alkyl group is 1 or more and 50 or less, 1 or more and 30 or less, 1 or more and 20 or less, 1 or more and 10 or less, or 1 or more and 6 or less. Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, t-butyl group, i-butyl group, 2-ethylbutyl group, 3, 3-dimethylbutyl group , n-pentyl group, i-pentyl group, neopentyl group, t-pentyl group, cyclopentyl group, 1-methylpentyl group, 3-methylpentyl group, 2-ethylpentyl group, 4-methyl-2-pentyl group , n-hexyl group, 1-methylhexyl group, 2-ethylhexyl group, 2-butylhexyl group, cyclohexyl group, 4-methylcyclohexyl group, 4-t-butylcyclohexyl group, n-heptyl group, 1 -Methylheptyl group, 2,2-dimethylheptyl group, 2-ethylheptyl group, 2-butylheptyl group, n-octyl group, t-octyl group, 2-ethyloctyl group, 2-butyloctyl group, 2-hexyl group Siloctyl group, 3,7-dimethyloctyl group, cyclooctyl group, n-nonyl group, n-decyl group, adamantyl group, 2-ethyldecyl group, 2-butyldecyl group, 2-hexyldecyl group, 2-ox Tyldecyl group, n-undecyl group, n-dodecyl group, 2-ethyldodecyl group, 2-butyldodecyl group, 2-hexyldodecyl group, 2-octyldodecyl group, n-tridecyl group, n-tetradecyl group, n -Pentadecyl group, n-hexadecyl group, 2-ethylhexadecyl group, 2-butylhexadecyl group, 2-hexylhexadecyl group, 2-octylhexadecyl group, n-heptadecyl group, n-octadecyl group , n-nonadecyl group, n-icosyl group, 2-ethyl icosyl group, 2-butyl icosyl group, 2-hexyl icosyl group, 2-octyl icosyl group, n-henicosyl group, n-docosyl group, n-tricho Sil group, n-tetracosyl group, n-pentacosyl group, n-hexacosyl group, n-heptacosyl group, n-octacosyl group, n-nonacosyl group, n-triacontyl group, etc. are mentioned, It is not limited to these.

As used herein, the hydrocarbon ring group means any functional group or substituent derived from an aliphatic hydrocarbon ring. The hydrocarbon ring group may be a saturated hydrocarbon ring group having 5 to 20 ring carbon atoms.

As used herein, the aryl group means any functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. The number of ring carbon atoms of the aryl group may be 6 or more and 30 or less, 6 or more and 20 or less, or 6 or more and 15 or less. Examples of the aryl group include a phenyl group, a naphthyl group, a fluorenyl group, an anthracenyl group, a phenanthryl group, a biphenyl group, a terphenyl group, a quarterphenyl group, a quinquephenyl group, a sexyphenyl group, a triphenylenyl group, a pyrenyl group, a benzofluoro Although a lanthenyl group, a chrysenyl group, etc. can be illustrated, it is not limited to these.

In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. Examples of the case in which the fluorenyl group is substituted are as follows. However, the present invention is not limited thereto.

As used herein, the heterocyclic group refers to any functional group or substituent derived from a ring including at least one of B, O, N, P, Si and S as a hetero atom. The heterocyclic group includes an aliphatic heterocyclic group and an aromatic heterocyclic group. The aromatic heterocyclic group may be a heteroaryl group. The aliphatic heterocycle and the aromatic heterocycle may be monocyclic or polycyclic.

In the present specification, the heterocyclic group may include one or more of B, O, N, P, Si and S as a hetero atom. When the heterocyclic group includes two or more heteroatoms, the two or more heteroatoms may be the same as or different from each other. The heterocyclic group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group, and is a concept including a heteroaryl group. The number of ring carbon atoms of the heterocyclic group may be 2 or more and 30 or less, 2 or more and 20 or less, or 2 or more and 10 or less.

In the present specification, the aliphatic heterocyclic group may include one or more of B, O, N, P, Si and S as a hetero atom. The aliphatic heterocyclic group may have 2 or more and 30 or less, 2 or more and 20 or less, or 2 or more and 10 or less. Examples of the aliphatic heterocyclic group include an oxirane group, a thiirane group, a pyrrolidine group, a piperidine group, a tetrahydrofuran group, a tetrahydrothiophene group, a thiane group, a tetrahydropyran group, a 1,4-dioxane group, and the like, but are not limited thereto.

In the present specification, the heteroaryl group may include one or more of B, O, N, P, Si and S as a hetero atom. When the heteroaryl group includes two or more hetero atoms, the two or more hetero atoms may be the same as or different from each other. The heteroaryl group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The number of ring carbon atoms of the heteroaryl group may be 2 or more and 30 or less, 2 or more and 20 or less, or 2 or more and 10 or less. Examples of the heteroaryl group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a triazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, a triazole group, an acridyl group, a pyridazine group, a pyrazinyl group. group, quinoline group, quinazoline group, quinoxaline group, phenoxazine group, phthalazine group, pyridopyrimidine group, pyridopyrazine group, pyrazinopyrazine group, isoquinoline group, indole group, carbazole group, N-arylcarba Zol group, N-heteroarylcarbazole group, N-alkylcarbazole group, benzooxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, thienothiophene group, benzofuran group, a phenanthroline group, a thiazole group, an isoxazole group, an oxazole group, an oxadiazole group, a thiadiazole group, a phenothiazine group, a dibenzosilol group and a dibenzofuran group, but are not limited thereto.

In the present specification, the description of the above-described aryl group may be applied except that the arylene group is a divalent group. Except that the heteroarylene group is a divalent group, the description of the above-described heteroaryl group may be applied.

In the present specification, the silyl group includes an alkyl silyl group and an aryl silyl group. Examples of the silyl group include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. not limited

In the present specification, the amine group may include an alkyl amine group, an aryl amine group, or a heteroaryl amine group. The amine group may mean that a nitrogen atom is bonded to an alkyl group, an aryl group, or a heteroaryl group as defined above. Examples of the amino group include, but are not limited to, a methylamine group, a dimethylamine group, a phenylamine group, a diphenylamine group, a naphthylamine group, a 9-methyl-anthracenylamine group, and a triphenylamine group.

In the present specification, the thiol group may include an alkyl thio group and an aryl thio group. The thiol group may mean that a sulfur atom is bonded to an alkyl group or an aryl group as defined above. Examples of the thiol group include methylthio group, ethylthio group, propylthio group, pentylthio group, hexylthio group, octylthio group, dodecylthio group, cyclopentylthio group, cyclohexylthio group, phenylthio group, naphthylthio group and the like, but are not limited thereto.

In the present specification, the oxy group may mean that an oxygen atom is bonded to an alkyl group or an aryl group as defined above. The oxy group may include an alkoxy group and an aryl oxy group. The alkoxy group may be straight-chain, branched-chain or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but may be, for example, 1 or more and 20 or less or 1 or more and 10 or less. Examples of the oxy group include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, octyloxy, nonyloxy, decyloxy, benzyloxy, etc. it is not

In the present specification, the boron group may mean that a boron atom is bonded to an alkyl group or an aryl group as defined above. The boron group includes an alkyl boron group and an aryl boron group. Examples of the boron group include, but are not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a diphenylboron group, and a phenylboron group.

In the present specification, the alkenyl group may be linear or branched. Although carbon number is not specifically limited, 2 or more and 30 or less, 2 or more and 20 or less, or 2 or more and 10 or less. Examples of the alkenyl group include, but are not limited to, a vinyl group, a 1-butenyl group, a 1-pentenyl group, a 1,3-butadienyl aryl group, a styrenyl group, a styryl vinyl group, and the like.

In the present specification, the alkyl group among the alkylthio group, the alkylaryl group, the alkylamino group, the alkyl boron group, the alkyl silyl group, and the alkylamine group is the same as the above-described alkyl group.

In the present specification, the aryl group in the aryloxy group, the arylthio group, the arylamino group, the aryl boron group, the aryl silyl group, and the arylamine group is the same as the examples of the aryl group described above.

In the present specification, direct linkage may mean a single bond.

"는 연결되는 위치를 의미한다. On the other hand, in this specification "

" means the location to be connected.

Hereinafter, one embodiment of the present invention will be described with reference to the drawings.

1 is a plan view illustrating an exemplary embodiment of a display device DD. 2 is a cross-sectional view of a display device DD according to an exemplary embodiment. FIG. 2 is a cross-sectional view showing a portion corresponding to the line I-I' of FIG. 1 .

The display device DD may include a display panel DP and an optical layer PP disposed on the display panel DP. The display panel DP includes organic electroluminescent devices EDL-1, ED-2, and ED-3. The display device DD may include a plurality of organic electroluminescent devices ED-1, ED-2, and ED-3. The optical layer PP may be disposed on the display panel DP to control light reflected from the display panel DP by external light. The optical layer PP may include, for example, a polarizing layer or a color filter layer. Meanwhile, unlike illustrated in the drawings, the optical layer PP may be omitted in the display device DD according to an exemplary embodiment.

The display panel DP may include a base layer BS, a circuit layer DP-CL provided on the base layer BS, and a display element layer DP-ED. The display element layer DP-ED includes the pixel defining layer PDL, the organic electroluminescent devices ED-1, ED-2, and ED-3 disposed between the pixel defining layer PDL, and the organic electroluminescent device. An encapsulation layer TFE disposed on the ED-1, ED-2, and ED-3 may be included.

The base layer BS may be a member that provides a base surface on which the display element layer DP-ED is disposed. The base layer BS may be a glass substrate, a metal substrate, a plastic substrate, or the like. However, the embodiment is not limited thereto, and the base layer BS may be an inorganic layer, an organic layer, or a composite material layer.

In an embodiment, the circuit layer DP-CL may be disposed on the base layer BS, and the circuit layer DP-CL may include a plurality of transistors (not shown). Transistors (not shown) each have a control electrode, an input electrode, and an output electrode. In an embodiment, the circuit layer DP-CL is disposed on the base layer BS, and the circuit layer DP-CL includes a plurality of It may include transistors (not shown). Each of the transistors (not shown) may include a control electrode, an input electrode, and an output electrode. For example, the circuit layer DP-CL includes a switching transistor and a driving transistor for driving the organic electroluminescent elements ED-1, ED-2, and ED-3 of the display element layer DP-ED. may be doing

Each of the organic electroluminescent devices ED-1, ED-2, and ED-3 may have the structure of the organic electroluminescent device ED of an embodiment according to FIGS. 3 to 6 to be described later. Each of the organic electroluminescent devices ED-1, ED-2, and ED-3 includes a first electrode EL1, a hole transport region HTR, a light emitting layer EML-R, EML-G, EML-B, and an electron. It may include a transport region ETR and a second electrode EL2 .

In FIG. 2 , the emission layers EML-R, EML-G, and EML-B of the organic electroluminescent devices ED-1, ED-2, and ED-3 in the opening OH defined in the pixel defining layer PDL. is disposed, and the hole transport region HTR, the electron transport region ETR, and the second electrode EL2 are provided as a common layer in all of the organic electroluminescent devices ED-1, ED-2, and ED-3. Examples are shown. However, the exemplary embodiment is not limited thereto, and unlike that illustrated in FIG. 2 , in an exemplary embodiment, the hole transport region HTR and the electron transport region ETR are located inside the opening OH defined in the pixel defining layer PDL. It may be provided after being patterned. For example, in one embodiment, the hole transport region (HTR) of the organic electroluminescent device (ED-1, ED-2, ED-3), the light emitting layer (EML-R, EML-G, EML-B), and the electron The transport region ETR and the like may be provided by being patterned by an inkjet printing method.

The encapsulation layer TFE may cover the organic electroluminescent devices ED-1, ED-2, and ED-3. The encapsulation layer TFE may encapsulate the display element layer DP-ED. The encapsulation layer TFE may be a thin-film encapsulation layer. The encapsulation layer TFE may be a single layer or a stack of a plurality of layers. The encapsulation layer TFE includes at least one insulating layer. The encapsulation layer TFE according to an embodiment may include at least one inorganic layer (hereinafter, referred to as an encapsulation inorganic layer). Also, the encapsulation layer TFE according to an embodiment may include at least one organic layer (hereinafter, referred to as an encapsulation organic layer) and at least one encapsulation inorganic layer.

The encapsulation inorganic film protects the display element layer DP-ED from moisture/oxygen, and the encapsulation organic film protects the display element layer DP-ED from foreign substances such as dust particles. The encapsulation inorganic layer may include silicon nitride, silicon oxynitride, silicon oxide, titanium oxide, or aluminum oxide, but is not particularly limited thereto. The encapsulation organic layer may include an acryl-based compound, an epoxy-based compound, or the like. The encapsulation organic layer may include a photopolymerizable organic material, and is not particularly limited.

The encapsulation layer TFE may be disposed on the second electrode EL2 , and may be disposed to fill the opening OH.

1 and 2 , the display device DD may include a non-emission area NPXA and light-emitting areas PXA-R, PXA-G, and PXA-B. Each of the light emitting regions PXA-R, PXA-G, and PXA-B may be a region from which light generated from each of the light emitting devices ED-1, ED-2, and ED-3 is emitted. The organic electroluminescent regions PXA-R, PXA-G, and PXA-B may be spaced apart from each other on a plane.

Each of the emission areas PXA-R, PXA-G, and PXA-B may be a region divided by the pixel defining layer PDL. The non-emission regions NPXA are regions between the neighboring emission regions PXA-R, PXA-G, and PXA-B, and may correspond to the pixel defining layer PDL. Meanwhile, in the present specification, each of the emission areas PXA-R, PXA-G, and PXA-B may correspond to a pixel. The pixel defining layer PDL may separate the organic electroluminescent devices ED-1, ED-2, and ED-3. The emission layers EML-R, EML-G, and EML-B of the organic electroluminescent devices ED-1, ED-2, and ED-3 are disposed in the opening OH defined in the pixel defining layer PDL. can be distinguished.

The light emitting regions PXA-R, PXA-G, and PXA-B may be divided into a plurality of groups according to the color of light generated by the organic electroluminescent devices ED-1, ED-2, and ED-3. . 3 light emitting regions PXA-R, PXA-G, and PXA-B emitting red light, green light, and blue light are exemplarily shown in the display device DD of the exemplary embodiment shown in FIGS. 1 and 2 . . For example, the display device DD according to an exemplary embodiment may include a red light emitting area PXA-R, a green light emitting area PXA-G, and a blue light emitting area PXA-B.

In the display device DD according to an exemplary embodiment, the plurality of organic electroluminescent devices ED-1, ED-2, and ED-3 may emit light of different wavelength ranges. For example, in an exemplary embodiment, the display device DD emits a first organic EL device ED-1 emitting red light, a second organic EL device ED-2 emitting green light, and a blue light emitting device. It may include a third organic electroluminescent device (ED-3). That is, the red light emitting area PXA-R, the green light emitting area PXA-G, and the blue light emitting area PXA-B of the display device DD are the first organic electroluminescent element ED-1 and the second light emitting area PXA-B, respectively. It may correspond to the 2nd organic electroluminescent element ED-2, and the 3rd organic electroluminescent element ED-3.

However, embodiments are not limited thereto, and the first to third organic electroluminescent devices ED-1, ED-2, and ED-3 emit light in the same wavelength region, or at least one has a different wavelength. It may be to emit light in the area. For example, all of the first to third organic electroluminescent devices ED-1, ED-2, and ED-3 may emit blue light.

The light emitting areas PXA-R, PXA-G, and PXA-B in the display device DD according to an exemplary embodiment may be arranged in a stripe shape. Referring to FIG. 1 , a plurality of red light-emitting areas PXA-R, a plurality of green light-emitting areas PXA-G, and a plurality of blue light-emitting areas PXA-B are respectively formed along a second direction axis DR2 . ) may be sorted. Also, the red light emitting area PXA-R, the green light emitting area PXA-G, and the blue light emitting area PXA-B may be alternately arranged in the order along the first direction axis DR1 .

1 and 2 show that the areas of the light emitting regions PXA-R, PXA-G, and PXA-B are all similar, but the embodiment is not limited thereto. The area of -B) may be different from each other depending on the wavelength region of the emitted light. Meanwhile, the area of the light emitting regions PXA-R, PXA-G, and PXA-B may mean an area when viewed on a plane defined by the first direction axis DR1 and the second direction axis DR2. .

Meanwhile, the arrangement of the light emitting areas PXA-R, PXA-G, and PXA-B is not limited to that illustrated in FIG. 1 , and includes a red light emitting area PXA-R, a green light emitting area PXA-G, and the order in which the blue light emitting areas PXA-B are arranged may be provided in various combinations according to characteristics of display quality required for the display device DD. For example, the arrangement of the light emitting regions PXA-R, PXA-G, and PXA-B may be a PENTILE® arrangement or a diamond arrangement.

Also, the areas of the light emitting regions PXA-R, PXA-G, and PXA-B may be different from each other. For example, in an exemplary embodiment, the area of the green light emitting area PXA-G may be smaller than the area of the blue light emitting area PXA-B, but the exemplary embodiment is not limited thereto.

Hereinafter, FIGS. 3 to 6 are cross-sectional views schematically illustrating an organic electroluminescent device according to an embodiment. The organic electroluminescent device ED according to an exemplary embodiment includes a first electrode EL1, a hole transport region HTR, a light emitting layer EML, an electron transport region ETR, and a second electrode EL2 that are sequentially stacked. may include

The organic electroluminescent device ED according to an embodiment includes the polycyclic compound according to an embodiment to be described later in the emission layer EML disposed between the first electrode EL1 and the second electrode EL2. However, the embodiment is not limited thereto, and the organic electroluminescent device ED according to an embodiment has a hole transport region that is a plurality of functional layers disposed between the first electrode EL1 and the second electrode EL2 in addition to the emission layer EML. The polycyclic compound according to an embodiment including the polycyclic compound according to an embodiment to be described later in the (HTR) or the electron transport region (ETR), or the polycyclic compound according to an embodiment to be described later in the capping layer CPL disposed on the second electrode EL2 may include

Meanwhile, in FIG. 4 , compared to FIG. 3 , the hole transport region HTR includes the hole injection layer HIL and the hole transport layer HTL, and the electron transport region ETR includes the electron injection layer EIL and the electron transport layer. A cross-sectional view of an organic electroluminescent device (ED) of an embodiment including (ETL) is shown. In addition, in FIG. 5 , the hole transport region (HTR) includes a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL) as compared with FIG. 3 , and the electron transport region (ETR) is an electron injection region A cross-sectional view of an organic electroluminescent device (ED) of an embodiment including a layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL) is shown. 6 is a cross-sectional view of the organic electroluminescent device ED according to an embodiment including the capping layer CPL disposed on the second electrode EL2 as compared with FIG. 4 .

The first electrode EL1 has conductivity. The first electrode EL1 may be formed of a metal alloy or a conductive compound. The first electrode EL1 may be an anode or a cathode. However, the embodiment is not limited thereto. Also, the first electrode EL1 may be a pixel electrode. The first electrode EL1 may be a transmissive electrode, a transflective electrode, or a reflective electrode. The first electrode EL1 is selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, and Zn. At least one, two or more compounds selected from these, a mixture of two or more selected from these, or an oxide thereof may be included. When the first electrode EL1 is a transmissive electrode, the first electrode EL1 is a transparent metal oxide, for example, indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium (ITZO). tin zinc oxide) and the like. When the first electrode EL1 is a transflective electrode or a reflective electrode, the first electrode EL1 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca (layered structure of LiF and Ca), LiF/Al (layered structure of LiF and Al), Mo, Ti, W, or a compound or mixture thereof (eg, a mixture of Ag and Mg) have. Alternatively, a plurality of layer structures including a reflective or semi-transmissive film formed of the above material and a transparent conductive film formed of indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), etc. can be For example, the first electrode EL1 may have a three-layer structure of ITO/Ag/ITO, but is not limited thereto. The thickness of the first electrode EL1 may be about 700 Å to about 10000 Å. For example, the thickness of the first electrode EL1 may be about 1000 Å to about 3000 Å.

The hole transport region HTR is provided on the first electrode EL1 . The hole transport region HTR may include at least one of a hole injection layer HIL, a hole transport layer HTL, a hole buffer layer (not shown), and an electron blocking layer EBL. The thickness of the hole transport region HTR may be, for example, about 50 Å to about 15,000 Å.

The hole transport region HTR may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials.

For example, the hole transport region HTR may have a single-layer structure of the hole injection layer HIL or the hole transport layer HTL, or may have a single-layer structure including a hole injection material and a hole transport material. In addition, the hole transport region HTR has a single layer structure made of a plurality of different materials, or a hole injection layer HIL/hole transport layer HTL and a hole injection layer sequentially stacked from the first electrode EL1 . (HIL) / hole transport layer (HTL) / hole buffer layer (not shown), hole injection layer (HIL) / hole buffer layer (not shown), hole transport layer (HTL) / hole buffer layer, or hole injection layer (HIL) / hole transport layer (HTL)/electron blocking layer (EBL) may have a structure, but the embodiment is not limited thereto.

Hole transport region (HTR), vacuum deposition method, spin coating method, casting method, LB method (Langmuir-Blodgett), inkjet printing method, laser printing method, laser thermal imaging (Laser Induced Thermal Imaging, LITI), such as various methods It can be formed using

The hole transport region (HTR) may further include a compound represented by the following Chemical Formula H-1.

[Formula H-1]

In Formula H-1, L ₁ and L ₂ are each independently a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring carbon number 2 or more It may be 30 or less heteroarylene groups. a and b may each independently be an integer of 0 or more and 10 or less. On the other hand, when a or b is an integer of 2 or more, a plurality of L ₁ and L ₂ are each independently a substituted or unsubstituted arylene group having 6 or more and 30 or less ring carbon atoms, or a substituted or unsubstituted ring carbon number of 2 or more and 30 or less It may be a heteroarylene group of.

In Formula H-1, Ar ₁ and Ar ₂ may each independently be a substituted or unsubstituted aryl group having 6 or more and 30 or less ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring carbon atoms. . In addition, in Formula H-1, Ar ₃ may be a substituted or unsubstituted aryl group having 6 or more and 30 or less ring carbon atoms.

The compound represented by Formula H-1 may be a monoamine compound. Alternatively, the compound represented by Formula H-1 may be a diamine compound in which at least one of Ar ₁ to Ar ₃ includes an amine group as a substituent. In addition, the compound represented by Formula H-1 is a carbazole-based compound including a carbazole group substituted or unsubstituted in at least one of Ar ₁ and Ar ₂ , or a carbazole-based compound including a carbazole group substituted or unsubstituted in at least one of Ar ₁ and Ar ₂ It may be a fluorene-based compound including a fluorene group.

The compound represented by Formula H-1 may be represented by any one of compounds of the following compound group H. However, the compounds listed in the following compound group H are exemplary, and the compound represented by the formula (H-1) is not limited to those shown in the following compound group H.

[Compound group H]

The hole transport region (HTR) is a phthalocyanine compound such as copper phthalocyanine, DNTPD(N ¹ ,N ^1' -([1,1'-biphenyl]-4,4'-diyl)bis(N) ¹ -phenyl-N ⁴ ,N ⁴ -di-m-tolylbenzene-1,4-diamine)), m-MTDATA(4,4',4"-[tris(3-methylphenyl)phenylamino] triphenylamine), TDATA( 4,4'4"-Tris(N,N-diphenylamino)triphenylamine), 1-TNATA(4,4',4"-tris[N(1-naphthyl)-N-phenylamino]-triphenylamine), 2-TNATA (4,4',4"-tris[N(2-naphthyl)-N-phenylamino]-triphenylamine), PEDOT/PSS(Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate)), PANI/DBSA (Polyaniline/Dodecylbenzenesulfonic acid), PANI/CSA(Polyaniline/Camphor sulfonicacid), PANI/PSS(Polyaniline/Poly(4-styrenesulfonate)), NPB(N,N'-di(naphthalene-l-yl)-N,N '-diphenyl-benzidine), polyether ketone containing triphenylamine (TPAPEK), 4-Isopropyl-4'-methyldiphenyliodonium [Tetrakis(pentafluorophenyl)borate], HATCN(dipyrazino[2,3-f: 2',3 '-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile) and the like may be further included.

The hole transport region (HTR) is, for example, a carbazole-based derivative such as N-phenylcarbazole or polyvinylcarbazole, a fluorene-based derivative, or TPD (N,N'-bis(3-methylphenyl)-N). Triphenylamine derivatives such as ,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine), TCTA (4,4',4"-tris(N-carbazolyl)triphenylamine), NPB (N,N'-di(naphthalene-l-yl)-N,N'-diphenyl-benzidine), TAPC(4,4′-Cyclohexylidene bis[N,N-bis(4-methylphenyl)benzenamine]), HMTPD (4,4'-Bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl), mCP(1,3-Bis(N-carbazolyl)benzene), etc. may be further included. .

The hole transport region (HTR) is CzSi(9-(4-tert-Butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole), CCP(9-phenyl-9H-3,9'-bicarbazole), or It may further include mDCP (1,3-bis(1,8-dimethyl-9H-carbazol-9-yl)benzene).

The hole transport region HTR may include the above-described compounds of the hole transport region in at least one of the hole injection layer HIL, the hole transport layer HTL, and the electron blocking layer EBL.

The hole transport region HTR may have a thickness of about 100 Å to about 10000 Å, for example, about 100 Å to about 5000 Å. The thickness of the hole injection layer HIL may be, for example, about 30 Å to about 1000 Å, and the thickness of the hole transport layer HTL may be about 30 Å to about 1000 Å. For example, the thickness of the electron blocking layer (EBL) may be about 10 Å to about 1000 Å. When the thicknesses of the hole transport region (HTR), the hole injection layer (HIL), the hole transport layer (HTL), and the electron blocking layer (EBL) satisfy the above-described ranges, satisfactory hole transport characteristics without a substantial increase in driving voltage can get

The hole transport region HTR may further include a charge generating material to improve conductivity, in addition to the aforementioned materials. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region HTR. The charge generating material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. For example, non-limiting examples of p-dopants include quinone derivatives such as TCNQ (Tetracyanoquinodimethane) and F4-TCNQ (2,3,5,6-tetrafluoro-7,7'8,8-tetracyanoquinodimethane), tungsten oxide, and the like. and metal oxides such as molybdenum oxide, etc., but is not limited thereto.

As described above, the hole transport region HTR may further include at least one of a hole buffer layer (not shown) and an electron blocking layer EBL, in addition to the hole injection layer HIL and the hole transport layer HTL. The hole buffer layer (not shown) may increase light emission efficiency by compensating for a resonance distance according to a wavelength of light emitted from the emission layer EML. As a material included in the hole buffer layer (not shown), a material capable of being included in the hole transport region HTR may be used. The electron blocking layer EBL is a layer serving to prevent electron injection from the electron transport region ETR to the hole transport region HTR.

The emission layer EML is provided on the hole transport region HTR. The emission layer EML may have a thickness of, for example, about 100 Å to about 1000 Å, or about 100 Å to about 300 Å. The emission layer EML may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials.

The organic electroluminescent device (ED) according to an embodiment may include the polycyclic compound according to the embodiment. The polycyclic compound according to an embodiment may be represented by the following Chemical Formula 1.

[Formula 1]

In Formula 1, X ₁ to X ₂ are each independently O, S, or NR ₇ , R ₇ is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring It is an aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, or bonded to an adjacent group to form a ring.

In Formula 1, R ₁ to R ₄ , R _5-1 to R _5-3 and R _6-1 to R _6-3 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a nitro group, a cyano group, or a hydroxyl group , a substituted or unsubstituted amine group, a substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 or more and 20 or less carbon atoms, a substituted or unsubstituted aryl group having 6 or more and 30 or less ring carbon atoms, a substituted or unsubstituted It is a heteroaryl group having 2 or more and 30 or less ring carbon atoms, or it combines with an adjacent group to form a ring.

In Formula 1, e and f are each independently an integer of 0 or more and 4 or less. On the other hand, when e is 2 or more, a plurality of R ₁ are the same as or different from each other, and when f is 2 or more, a plurality of R ₂ are the same or different from each other.

In Formula 1, g is an integer of 0 or more and 2 or less, on the other hand, when g is 2 or more, a plurality of R ₃ are the same as or different from each other.

In Formula 1, h is an integer of 0 or more and 3 or less, on the other hand, when h is 2 or more, a plurality of R ₄ are the same as or different from each other.

In Formula 1, Y ₁ , and Y ₂ are each independently each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 6 or more and 20 or less carbon atoms, a substituted or unsubstituted ring-forming carbon number of 6 or more and 30 or less an aryl group, or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring carbon atoms. However, at least one of Y ₁ and Y ₂ is a substituted or unsubstituted alkyl group having 6 or more and 20 or less carbon atoms, a substituted or unsubstituted aryl group having 6 or more and 30 or less ring carbon atoms, or a substituted or unsubstituted ring carbon number 2 or more and 30 or less heteroaryl groups.

In one embodiment, at least one of X ₁ and X ₂ in Formula 1 is NR ₇ , R ₇ is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring carbon number 2 It may be a heteroaryl group of 30 or more. For example, Chemical Formula 1 may be represented by any one of Chemical Formulas 2-1 to 2-5 below.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

In Formulas 2-1 to 2-5, Ar_1-1and Ar_1-2may be each independently a substituted or unsubstituted aryl group having 6 or more and 30 or less ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring carbon atoms.

In Formulas 2-1 to 2-5, R ₁ to R ₄ , R _5-1 to R _{5-3 ,} R _6-1 to R _6-3 , Y ₁ , Y ₂ , and e to h are in Formula 1 same as defined in

In an embodiment, Ar _1-1 and Ar _1-2 may each independently be represented by any one of the following Chemical Formulas 5-1 to 5-3.

[Formula 5-1]

[Formula 5-2]

[Formula 5-3]

In Formulas 5-1 to 5-3, R _a1 to R _a5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted ring carbon number It may be an aryl group of 6 or more and 30 or less, or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring carbon atoms.

In Formula 5-1, m1 is an integer of 0 or more and 5 or less, on the other hand, when m1 is 2 or more, a plurality of R _a1s are the same as or different from each other.

In Formula 5-2, m2 is an integer of 0 or more and 9 or less, on the other hand, when m2 is 2 or more, a plurality of R _a2 are the same as or different from each other.

In Formula 5-3, m3 is an integer of 0 or more and 5 or less, on the other hand, when m3 is 2 or more, a plurality of R _a3 are the same as or different from each other.

In Formula 5-3, m4 is an integer of 0 or more and 3 or less, on the other hand, when m4 is 2 or more, a plurality of R _a4 are the same as or different from each other.

In Formula 5-3, m5 is an integer of 0 or more and 5 or less, on the other hand, when m5 is 2 or more, a plurality of R _a5 are the same as or different from each other.

In one embodiment, R _5-1 to R _5-3 of Formula 1, and At least one of R _6-1 to R _6-3 may be a substituted amine group.

In one embodiment, R _5-2 in Formula 1 may be a substituted amine group. For example, Chemical Formula 1 may be represented by Chemical Formula 3-1 below.

[Formula 3-1]

In Formula 3-1, Ar _3-1 and Ar _3-2 may each independently be a substituted or unsubstituted aryl group having 6 or more and 30 or less ring carbon atoms, X ₁ , X ₂ , R ₁ to R ₄ , R _5-1 , R _{5-3 ,} R _6-1 to R _6-3 , Y ₁ , Y ₂ , and e to h are the same as defined in Formula 1 .

In one embodiment, R _6-2 of Formula 1 may be a substituted amine group. For example, Formula 1 may be represented by Formula 3-2 below.

[Formula 3-2]

In Formula 3-2, Ar _4-1 and Ar _4-2 may be each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, X ₁ , X ₂ , R ₁ to R ₄ , R _5-1 to R _5-3, R _{6 -1} , R _6-3 , Y ₁ , Y ₂ , and e to h are the same as defined in Formula 1.

In one embodiment, R _5-2 and R _6-2 of Formula 1 may each be a substituted amine group. For example, Chemical Formula 1 may be represented by Chemical Formula 4 below.

[Formula 4]

In Formula 4, Ar _3-1, Ar _3-2 , Ar _4-1 and Ar _4-2 may be each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, X ₁ , X ₂ , R ₁ to R ₄ , R _5-1 , R _5-3, R _{6 -1} , R _6-3 , Y ₁ , Y ₂ , and e to h are the same as defined in Formula 1.

In one embodiment, in Formula 3-1 or Formula 4, Ar _3-1, and Ar _3-2 may be each independently a substituted or unsubstituted aryl group having 6 or more and 18 or less ring carbon atoms.

In one embodiment, in Formula 3-2 or Formula 4, Ar _4-1 and Ar _4-2 may be each independently a substituted or unsubstituted aryl group having 6 or more and 18 or less ring carbon atoms.

The polycyclic compound represented by Formula 1 according to an embodiment of the present invention may be any one selected from the compounds shown in Compound Group 1 below. However, the present invention is not limited thereto.

[Compound group 1]

1`14

1`14

.

.

The polycyclic compound of one embodiment represented by Formula 1 and the like may be used as a fluorescent light emitting material or a thermally activated delayed fluorescence (TADF) material. For example, the polycyclic compound of one embodiment may be used as a fluorescent dopant material or TADF dopant material emitting blue light. The polycyclic compound according to an embodiment may be a light emitting material having a light emission center wavelength (λ _max ) in a wavelength region of 490 nm or less. For example, the polycyclic compound of an embodiment represented by Formula 1 may be a light emitting material having an emission center wavelength in a wavelength region of 450 nm or more and 470 nm or less. That is, the polycyclic compound of an embodiment may be a blue thermally activated delayed fluorescent dopant. However, the embodiment is not limited thereto.

In the organic electroluminescent device ED of the exemplary embodiment shown in FIGS. 3 to 6 , the emission layer EML may include a first compound and a second compound. For example, the first compound may include a dopant, and the second compound may include a host. In one embodiment, the first compound may be a polycyclic compound represented by Formula 1.

The polycyclic compound according to an embodiment of the present invention increases k _RISC as the spin orbital interaction increases due to the heavy atom effect caused by the introduction of sulfur element, so that Triplet-Triplet Annihilation (TTA), and Singlet-Triplet Annihilation (STA) ) can be suppressed. In addition, the polycyclic compound of an embodiment represented by Formula 1 and the like essentially includes a substituent Y ₁ and/or Y ₂ at a specific position, thereby increasing the molecular volume to widen the distance between adjacent molecules in an excited state, so that TTA, and STA can be suppressed. Accordingly, the organic electroluminescent device (ED) of an embodiment including the polycyclic compound of an embodiment in the light emitting layer (EML) may suppress roll-off and exhibit improved lifespan characteristics.

In addition, the organic electroluminescent device (ED) of an embodiment including the polycyclic compound of an embodiment represented by Formula 1 in the light emitting layer (EML) may emit delayed fluorescence. The organic electroluminescent device (ED) of an embodiment may emit thermally activated delayed fluorescence (TADF), and the organic electroluminescent device (ED) may exhibit high efficiency characteristics.

The organic electroluminescent device (ED) of an embodiment may further include the following light emitting layer material in addition to the polycyclic compound of the embodiment described above. In the organic electroluminescent device (ED) of an embodiment, the emission layer (EML) may include an anthracene derivative, a pyrene derivative, a fluoranthene derivative, a chrysene derivative, a dihydrobenzanthracene derivative, or a triphenylene derivative. Specifically, the emission layer EML may include an anthracene derivative or a pyrene derivative.

In the organic electroluminescent device (ED) of an embodiment shown in FIGS. 3 to 6 , the emission layer (EML) may include a host and a dopant, and the emission layer (EML) may include a compound represented by the following Chemical Formula E-1. can The compound represented by the following Chemical Formula E-1 may be used as a fluorescent host material.

[Formula E-1]

In Formula E-1, R ₃₁ to R ₄₀ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted Or an unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring forming group It may be a heteroaryl group having 2 or more and 30 or less carbon atoms, or may be combined with an adjacent group to form a ring. Meanwhile, R ₃₁ to R ₄₀ may combine with adjacent groups to form a saturated hydrocarbon ring, an unsaturated hydrocarbon ring, a saturated hetero ring, or an unsaturated hetero ring.

In Formula E-1, c and d may each independently be an integer of 0 or more and 5 or less.

Formula E-1 may be represented by any one of the following compounds E1 to E19.

In an embodiment, the emission layer EML may include a compound represented by the following Chemical Formula E-2a or Chemical Formula E-2b. The compound represented by Formula E-2a or Formula E-2b below may be used as a phosphorescent host material.

[Formula E-2a]

In Formula E-2a, a is an integer from 0 to 10, and L _a is a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring carbon number 2 to 30 It may be the following heteroarylene group. On the other hand, when a is an integer of 2 or more, a plurality of L _a are each independently a substituted or unsubstituted arylene group having 6 or more and 30 or less ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 or more and 30 or less ring carbon atoms can

In addition, in Formula E-2a, A ₁ to A ₅ may each independently represent N or CR _i . R _a to R _i are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group, a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted C1 or more and 20 or less of an alkyl group, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms Or, it may be combined with an adjacent group to form a ring. R _a to R _i may combine with an adjacent group to form a hydrocarbon ring or a hetero ring including N, O, S, etc. as ring forming atoms.

Meanwhile, in Formula E-2a, two or three selected from A ₁ to A ₅ may be N and the rest may be CR _i .

[Formula E-2b]

In Formula E-2b, Cbz1 and Cbz2 may each independently represent an unsubstituted carbazole group or a carbazole group substituted with an aryl group having 6 to 30 ring carbon atoms. L _b may be a direct bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms. b is an integer of 0 or more and 10 or less, and when b is an integer of 2 or more, a plurality of L _b are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring carbon number 2 It may be a heteroarylene group of 30 or more.

The compound represented by Formula E-2a or Formula E-2b may be represented by any one of the compounds of the following compound group E-2. However, the compounds listed in the following compound group E-2 are exemplary, and the compounds represented by the formulas E-2a or E-2b are not limited to those shown in the following compound groups E-2.

[Compound group E-2]

The light emitting layer EML may further include a general material known in the art as a host material. For example, the light emitting layer (EML) is a host material as BCPDS (bis (4- (9H-carbazol-9-yl) phenyl) diphenylsilane), POPCPA ((4- (1- (4- (diphenylamino) phenyl) cyclohexyl) phenyl) diphenyl-phosphine oxide), DPEPO(Bis[2-(diphenylphosphino)phenyl] ether oxide), CBP(4,4'-bis(N-carbazolyl)-1,1'-biphenyl), mCP(1,3 -Bis(carbazol-9-yl)benzene), PPF (2,8-Bis(diphenylphosphoryl)dibenzo[b,d]furan), TCTA(4,4',4''-Tris(carbazol-9-yl) -triphenylamine) and TPBi(1,3,5-tris(1-phenyl-1H-benzo[d]imidazole-2-yl)benzene) may be included. However, the present invention is not limited thereto, and for example, Alq ₃ (tris(8-hydroxyquinolino)aluminum), ADN(9,10-di(naphthalene-2-yl)anthracene), TBADN(2-tert-butyl- 9,10-di(naphth-2-yl)anthracene), DSA(distyrylarylene), CDBP(4,4′-bis(9-carbazolyl)-2,2′-dimethyl-biphenyl), MADN(2-Methyl- 9,10-bis(naphthalen-2-yl)anthracene), CP1 (Hexaphenyl cyclotriphosphazene), UGH2 (1,4-Bis(triphenylsilyl)benzene), DPSiO ₃ (Hexaphenylcyclotrisiloxane), DPSiO ₄ (Octaphenylcyclotetra siloxane), etc. can be used as

The emission layer EML may include a compound represented by the following Chemical Formula M-a or Chemical Formula M-b. The compound represented by the following Chemical Formula M-a or Chemical Formula M-b may be used as a phosphorescent dopant material.

[Formula M-a]

In Formula Ma, Y ₁ to Y ₄ , and Z ₁ to Z ₄ are each independently CR ₁ or N, and R ₁ to R ₄ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted amine group. , a substituted or unsubstituted thio group, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted ring It may be an aryl group having 6 or more and 30 or less carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring carbon atoms, or may be bonded to adjacent groups to form a ring. In formula Ma, m is 0 or 1, and n is 2 or 3. In formula Ma, when m is 0, n is 3, and when m is 1, n is 2.

The compound represented by Formula M-a may be used as a red phosphorescent dopant or a green phosphorescent dopant.

The compound represented by Formula M-a may be represented by any one of the following compounds M-a1 to M-a25. However, the following compounds M-a1 to M-a25 are exemplary, and the compounds represented by the formula M-a are not limited to those represented by the following compounds M-a1 to M-a25.

The compound M-a1 and the compound M-a2 may be used as a red dopant material, and the compound M-a3 and the compound M-a4 may be used as a green dopant material.

[Formula M-b]

,

,

,

,

,

, 치환 또는 비치환된 탄소수 1 이상 20 이하의 2가의 알킬기, 치환 또는 비치환된 고리 형성 탄소수 6 이상 30 이하의 아릴렌기, 또는 치환 또는 비치환된 고리 형성 탄소수 2 이상 30 이하의 헤테로아릴렌기이고, e1 내지 e4는 각각 독립적으로 0 또는 1이다. R₃₁ 내지 R₃₉는 각각 독립적으로 수소 원자, 중수소 원자, 할로겐 원자, 시아노기, 치환 또는 비치환된 아민기, 치환 또는 비치환된 탄소수 1 이상 20 이하의 알킬기, 치환 또는 비치환된 고리 형성 탄소수 6 이상 30 이하의 아릴기, 또는 치환 또는 비치환된 고리 형성 탄소수 2 이상 30 이하의 헤테로아릴기이거나, 또는 인접하는 기와 서로 결합하여 고리를 형성하고, d1 내지 d4는 각각 독립적으로 0 이상 4 이하의 정수이다. In Formula Mb, Q ₁ to Q ₄ are each independently C or N, and C1 to C4 are each independently a substituted or unsubstituted hydrocarbon ring having 5 to 30 carbon atoms, or a substituted or unsubstituted ring carbon number 2 or more and 30 or less heterocyclic rings. L ₂₁ to L ₂₄ are each independently a direct bond,

,

,

,

,

,

, a substituted or unsubstituted divalent alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, and , e1 to e4 are each independently 0 or 1. R ₃₁ to R ₃₉ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted ring carbon number 6 or more and 30 or less aryl group, or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring carbon atoms, or combine with adjacent groups to form a ring, and d1 to d4 are each independently 0 or more and 4 or less is the integer of

The compound represented by Formula M-b may be used as a blue phosphorescent dopant or a green phosphorescent dopant.

The compound represented by Formula M-b may be represented by any one of the following compounds. However, the following compounds are exemplary and the compound represented by Formula M-b is not limited to those represented by the following compounds.

In the above compounds, R, R ₃₈ , and R ₃₉ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, It may be a substituted or unsubstituted aryl group having 6 or more and 30 or less ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring carbon atoms.

The emission layer EML may include a compound represented by any one of the following Chemical Formulas F-a to F-c. The compounds represented by the following Chemical Formulas F-a to F-c may be used as a fluorescent dopant material.

[Formula F-a]

로 치환되는 것일 수 있다. R_a 내지 R_j 중

로 치환되지 않은 나머지들은 각각 독립적으로 수소 원자, 중수소 원자, 할로겐 원자, 시아노기, 치환 또는 비치환된 아민기, 치환 또는 비치환된 탄소수 1 이상 20 이하의 알킬기, 치환 또는 비치환된 고리 형성 탄소수 6 이상 30 이하의 아릴기, 또는 치환 또는 비치환된 고리 형성 탄소수 2 이상 30 이하의 헤테로아릴기일 수 있다.

에서 Ar₁ 및 Ar₂는 각각 독립적으로, 치환 또는 비치환된 고리 형성 탄소수 6 이상 30 이하의 아릴기, 또는 치환 또는 비치환된 고리 형성 탄소수 2 이상 30 이하의 헤테로아릴기일 수 있다. 예를 들어, Ar₁ 및 Ar₂ 중 적어도 하나는 고리 형성 원자로 O 또는 S를 포함하는 헤테로아릴기일 수 있다.In Formula Fa, two selected from R _a to R _j are each independently

may be substituted with of R _a to R _j

Residues not substituted with are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring carbon number It may be an aryl group of 6 or more and 30 or less, or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring carbon atoms.

In Ar ₁ and Ar ₂ may each independently be a substituted or unsubstituted aryl group having 6 or more and 30 or less ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring carbon atoms. For example, at least one of Ar ₁ and Ar ₂ may be a heteroaryl group including O or S as a ring-forming atom.

[Formula F-b]

In Formula Fb, R _a and R _b are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or It may be an unsubstituted aryl group having 6 or more and 30 or less ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring carbon atoms, or bonding with adjacent groups to form a ring. Ar ₁ to Ar ₄ may each independently be a substituted or unsubstituted aryl group having 6 or more and 30 or less ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring carbon atoms.

In Formula F-b, U and V may each independently be 0 or 1. In Formula F-b, U means the number of rings bonded to the U position and V means the number of rings bonded to the V position. For example, when U or V is 1, the ring in which U or V is described constitutes a condensed ring, and when U or V is 0, it means that the ring in which U or V is described does not exist. Specifically, when U is 0 and V is 1, or when U is 1 and V is 0, the condensed ring having a fluorene core of Formula F-b may be a tetracyclic compound. In addition, when both U and V are 0, the condensed ring of Formula F-b may be a tricyclic compound. In addition, when both U and V are 1, the condensed ring having a fluorene core of Formula F-b may be a 5-ring compound.

In Formula F-b, when U or V is 1, U and V are each independently a substituted or unsubstituted hydrocarbon ring having 5 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms. can be

[Formula F-c]

In Formula Fc, A ₁ and A ₂ are each independently O, S, Se, or NR _m , and R _m is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted It may be an aryl group having 6 or more and 30 or less ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring carbon atoms. R ₁ to R ₁₁ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted boyl group, a substituted or substituted oxy group, a substituted or unsubstituted A thio group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, or , or adjacent groups combine with each other to form a ring.

In Formula Fc, A ₁ and A ₂ may each independently combine with a substituent of a neighboring ring to form a condensed ring. For example, when A ₁ and A ₂ are each independently NR _m , A ₁ may be combined with R ₄ or R ₅ to form a ring. In addition, A ₂ may be combined with R ₇ or R ₈ to form a ring.

In an embodiment, the light emitting layer (EML) is a known dopant material, and a styryl derivative (eg, 1,4-bis[2-(3-N-ethylcarbazoryl)vinyl]benzene(BCzVB), 4-(di-) p-tolylamino)-4'-[(di-p-tolylamino)styryl]stilbene (DPAVB), N-(4-((E)-2-(6-((E)-4-(diphenylamino)styryl) naphthalen-2-yl)vinyl)phenyl)-N-phenylbenzenamine (N-BDAVBi)), perylene and its derivatives (eg, 2, 5, 8, 11-Tetra-t-butylperylene (TBP)), pyrene and derivatives thereof (eg, 1, 1-dipyrene, 1, 4-dipyrenylbenzene, 1, 4-Bis(N, N-Diphenylamino)pyrene) and the like.

The emission layer EML may include a known phosphorescent dopant material. For example, phosphorescent dopants include iridium (Ir), platinum (Pt), osmium (Os), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), and terbium (Tb). ) or a metal complex containing thulium (Tm) may be used. Specifically, FIrpic(iridium(III) bis(4,6-difluorophenylpyridinato-N,C2′)picolinate), Fir6(Bis(2,4-difluorophenylpyridinato)-tetrakis(1-pyrazolyl)borate iridium(III)), or Platinum octaethyl porphyrin (PtOEP) may be used as a phosphorescent dopant. However, the embodiment is not limited thereto.

3 to 6 , the electron transport region ETR is provided on the emission layer EML. The electron transport region ETR may include at least one of a hole blocking layer HBL, an electron transport layer ETL, and an electron injection layer EIL, but embodiments are not limited thereto.

The electron transport region ETR may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials.

For example, the electron transport region ETR may have a single layer structure of the electron injection layer EIL or the electron transport layer ETL, or may have a single layer structure including an electron injection material and an electron transport material. In addition, the electron transport region ETR has a single layer structure made of a plurality of different materials, or an electron transport layer (ETL)/electron injection layer (EIL), a hole blocking layer ( HBL)/electron transport layer (ETL)/electron injection layer (EIL) structure, but is not limited thereto. The thickness of the electron transport region ETR may be, for example, about 1000 Å to about 1500 Å.

Electron transport region (ETR), vacuum deposition method, spin coating method, casting method, LB method (Langmuir-Blodgett), inkjet printing method, laser printing method, laser thermal imaging (Laser Induced Thermal Imaging, LITI), such as various methods It can be formed using

The electron transport region (ETR) may include a compound represented by the following Chemical Formula ET-1.

[Formula ET-1]

In Formula ET-1, at least one of X ₁ to X ₃ is N and the rest is CR _a . R _a is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring carbon number 2 to 30 It may be the following heteroaryl group. Ar ₁ to Ar ₃ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted It may be a heteroaryl group having 2 or more and 30 or less ring carbon atoms.

In Formula ET-1, a to c may each independently be an integer of 0 to 10 or less. In Formula ET-1, L ₁ to L ₃ are each independently a direct linkage, a substituted or unsubstituted arylene group having 6 or more and 30 or less ring carbon atoms, or a substituted or unsubstituted ring carbon number of 2 or more and 30 or less It may be a heteroarylene group of. On the other hand, when a to c are an integer of 2 or more, L ₁ to L ₃ are each independently a substituted or unsubstituted arylene group having 6 or more and 30 or less ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 or more and 30 or less ring carbon atoms. It may be an arylene group.

When the electron transport region ETR includes the electron transport layer ETL, the electron transport region ETR may include an anthracene-based compound. However, the present invention is not limited thereto, and the electron transport region is, for example, Alq ₃ (Tris(8-hydroxyquinolinato)aluminum), 1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene, 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)-1,3,5-triazine, 2-(4-(N-phenylbenzoimidazol-1-yl)phenyl)- 9,10-dinaphthylanthracene, TPBi(1,3,5-Tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene), BCP(2,9-Dimethyl-4,7-diphenyl-1 ,10-phenanthroline), Bphen(4,7-Diphenyl-1,10-phenanthroline), TAZ(3-(4-Biphenylyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole), NTAZ(4-(Naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole), tBu-PBD(2-(4-Biphenylyl)-5-(4-tert-butylphenyl) -1,3,4-oxadiazole), BAlq(Bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-Biphenyl-4-olato)aluminum), Bebq ₂ (berylliumbis(benzoquinolin-10) -olate)), ADN (9,10-di(naphthalene-2-yl)anthracene), BmPyPhB(1,3-Bis[3,5-di(pyridin-3-yl)phenyl]benzene) and mixtures thereof may include.

The electron transport region (ETR) may include at least one of the following compounds ET1 to ET36.

In addition, the electron transport region ETR may include a metal halide such as LiF, NaCl, CsF, RbCl, RbI, CuI, KI, a lanthanide metal such as Yb, and a co-deposition material of the above metal halide and the lanthanide metal. can For example, the electron transport region ETR may include KI:Yb, RbI:Yb, LiF:Yb, or the like as a co-deposition material. Meanwhile, as the electron transport region ETR, a metal oxide such as Li ₂ O, BaO, or 8-hydroxyl-Lithium quinolate (Liq) may be used, but the embodiment is not limited thereto. The electron transport region ETR may also be formed of a material in which an electron transport material and an insulating organo metal salt are mixed. The organometallic salt may be a material having an energy band gap of about 4 eV or more. Specifically, for example, the organometallic salt may include metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate or metal stearate. However, the embodiment is not limited thereto.

The electron transport region ETR may include the above-described electron transport region compounds in at least one of the electron injection layer EIL, the electron transport layer ETL, and the hole blocking layer HBL.

When the electron transport region ETR includes the electron transport layer ETL, the thickness of the electron transport layer ETL may be about 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer ETL satisfies the above range, a satisfactory electron transport characteristic may be obtained without a substantial increase in driving voltage. In this case, the thickness of the electron injection layer EIL may be about 1 Å to about 100 Å, or about 3 Å to about 90 Å. When the thickness of the electron injection layer EIL satisfies the above-described range, a satisfactory level of electron injection characteristics may be obtained without a substantial increase in driving voltage.

The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 may be a common electrode. The second electrode EL2 may be a cathode or an anode, but the embodiment is not limited thereto. For example, when the first electrode EL1 is an anode, the second electrode EL2 may be a cathode, and when the first electrode EL1 is a cathode, the second electrode EL2 may be an anode. The second electrode is at least one selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF, Mo, Ti, W, In, Sn, and Zn; It may include two or more compounds selected from these, a mixture of two or more selected from these, or oxides thereof.

The second electrode EL2 may be a transmissive electrode, a transflective electrode, or a reflective electrode. When the second electrode EL2 is a transmissive electrode, the second electrode EL2 is a transparent metal oxide, for example, indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium (ITZO). tin zinc oxide) and the like.

When the second electrode EL2 is a transflective electrode or a reflective electrode, the second electrode EL2 may include Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/Ca, LiF/Al, Mo, Ti, Yb, W, or a compound or mixture comprising these (eg, AgMg, AgYb, or MgAg). Alternatively, the second electrode EL2 may be a reflective or semi-transmissive layer formed of the above material, and a transparent conductive material formed of indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), or the like. It may be a multi-layer structure comprising a film. For example, the second electrode EL2 may include the aforementioned metal material, a combination of two or more metal materials selected from among the aforementioned metal materials, or an oxide of the aforementioned metal materials.

Although not shown, the second electrode EL2 may be connected to the auxiliary electrode. When the second electrode EL2 is connected to the auxiliary electrode, the resistance of the second electrode EL2 may be reduced.

Meanwhile, a capping layer CPL may be further disposed on the second electrode EL2 of the light emitting device ED according to an exemplary embodiment. The capping layer CPL may include multiple layers or a single layer.

In an embodiment, the capping layer CPL may be an organic layer or an inorganic layer. For example, when the capping layer CPL includes an inorganic material, the inorganic material may include an alkali metal compound such as LiF, an alkaline earth metal compound such as MgF ₂ , SiON, SiN _X , SiOy, or the like.

For example, when the capping layer (CPL) includes an organic material, the organic material is α-NPD, NPB, TPD, m-MTDATA, Alq ₃ , CuPc, TPD15(N4,N4,N4',N4'-tetra (biphenyl) -4-yl) biphenyl-4,4'-diamine), TCTA (4,4',4"-Tris (carbazol sol-9-yl) triphenylamine), etc., or such as epoxy resin, or methacrylate It may include an acrylate, but the embodiment is not limited thereto, and may include the following compounds P1 to P5.

Meanwhile, the refractive index of the capping layer CPL may be 1.6 or more. Specifically, the refractive index of the capping layer CPL may be 1.6 or more with respect to light in a wavelength range of 550 nm or more and 660 nm or less.

7 and 8 are cross-sectional views of a display device according to an exemplary embodiment, respectively. Hereinafter, in the description of the display device according to the exemplary embodiment described with reference to FIGS. 7 and 8 , the content overlapping with the content described with reference to FIGS. 1 to 6 will not be described again, and will be mainly described with reference to differences.

Referring to FIG. 7 , a display device DD according to an exemplary embodiment includes a display panel DP including a display element layer DP-ED, a light control layer CCL disposed on the display panel DP, and It may include a color filter layer (CFL).

In the exemplary embodiment illustrated in FIG. 7 , the display panel DP includes a base layer BS, a circuit layer DP-CL provided on the base layer BS, and a display element layer DP-ED. The device layer DP-ED may include an organic electroluminescent device ED.

The organic electroluminescent device ED includes a first electrode EL1 , a hole transport region HTR disposed on the first electrode EL1 , an emission layer EML disposed on the hole transport region HTR, and an emission layer EML ) may include an electron transport region ETR disposed on the electron transport region ETR, and a second electrode EL2 disposed on the electron transport region ETR. On the other hand, the structure of the organic electroluminescent device (ED) shown in FIG. 7 may be the same as that of the organic electroluminescent device of FIGS. 3 to 6 described above.

Referring to FIG. 7 , the emission layer EML may be disposed in the opening OH defined in the pixel defining layer PDL. For example, the emission layer EML divided by the pixel defining layer PDL and provided corresponding to each of the emission regions PXA-R, PXA-G, and PXA-B may emit light of the same wavelength region. . In the display device DD according to an exemplary embodiment, the emission layer EML may emit blue light. Meanwhile, unlike illustrated, in an exemplary embodiment, the emission layer EML may be provided as a common layer in all of the emission regions PXA-R, PXA-G, and PXA-B.

The light control layer CCL may be disposed on the display panel DP. The light control layer CCL may include a light converter. The light converter may be a quantum dot or a phosphor. The light converter may convert the received light to a wavelength and emit it. That is, the light control layer CCL may be a layer including quantum dots or a layer including a phosphor.

The core of the quantum dot may be selected from a group II-VI compound, a group III-V compound, a group IV-VI compound, a group IV element, a group IV compound, and combinations thereof.

Group II-VI compounds include diatomic compounds selected from the group consisting of CdSe, CdTe, CdS, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, MgS, and mixtures thereof; CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgZnTe, HgZnS, HgZnSe, HgZnTe, MgZnS, MgZnS and mixtures of three members selected from the group consisting of: bovine compounds; and HgZnTeS, CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, HgZnSTe, and mixtures thereof.

The group III-VI compound may include a binary compound such as In ₂ S ₃ , In ₂ Se ₃ , or the like, a ternary compound such as InGaS ₃ , InGaSe ₃ , or the like, or any combination thereof.

The group I-III-VI compound is a ternary compound selected from the group consisting of AgInS, AgInS ₂ , CuInS, CuInS ₂ , AgGaS ₂ , CuGaS ₂ CuGaO ₂ , AgGaO ₂ , AgAlO ₂ and mixtures thereof, or AgInGaS ₂ , It may be selected from quaternary compounds such as CuInGaS ₂ .

The group III-V compound is a binary compound selected from the group consisting of GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, InSb, and mixtures thereof, GaNP, GaNAs, GaNSb, GaPAs , GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InAlP, InNP, InNAs, InNSb, InPAs, InPSb and a ternary compound selected from the group consisting of mixtures thereof, and GaAlNPs, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb , GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, InAlPSb, and may be selected from the group consisting of a quaternary compound selected from the group consisting of mixtures thereof. Meanwhile, the group III-V compound may further include a group II metal. For example, InZnP or the like may be selected as the group III-II-V compound.

The group IV-VI compound is a binary compound selected from the group consisting of SnS, SnSe, SnTe, PbS, PbSe, PbTe, and mixtures thereof; a ternary compound selected from the group consisting of SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and mixtures thereof; and a quaternary compound selected from the group consisting of SnPbSSe, SnPbSeTe, SnPbSTe, and mixtures thereof. The group IV element may be selected from the group consisting of Si, Ge, and mixtures thereof. The group IV compound may be a di-element compound selected from the group consisting of SiC, SiGe, and mixtures thereof.

In this case, the binary compound, the ternary compound, or the quaternary compound may be present in the particle at a uniform concentration, or may be present in the same particle as the concentration distribution is partially divided into different states. Also, one quantum dot may have a core/shell structure surrounding another quantum dot. The interface between the core and the shell may have a concentration gradient in which the concentration of elements present in the shell decreases toward the center.

In some embodiments, the quantum dots may have a core-shell structure including a core including the aforementioned nanocrystals and a shell surrounding the core. The shell of the quantum dot may serve as a protective layer for maintaining semiconductor properties by preventing chemical modification of the core and/or a charging layer for imparting electrophoretic properties to the quantum dots. The shell may be single-layered or multi-layered. The interface between the core and the shell may have a concentration gradient in which the concentration of elements present in the shell decreases toward the center. Examples of the shell of the quantum dot may include a metal or non-metal oxide, a semiconductor compound, or a combination thereof.

For example, the metal or non-metal oxide is SiO ₂ , Al ₂ O ₃ , TiO ₂ , ZnO, MnO, Mn ₂ O ₃ , Mn ₃ O ₄ , CuO, FeO, Fe ₂ O ₃ , Fe ₃ O ₄ , A binary compound such as CoO, Co ₃ O ₄ , NiO, or a ternary compound such as MgAl ₂ O ₄ , CoFe ₂ O ₄ , NiFe ₂ O ₄ , CoMn ₂ O ₄ may be exemplified, but the present invention is not limited thereto it is not

In addition, the semiconductor compound is exemplified by CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, etc. However, the present invention is not limited thereto.

The quantum dots may have a full width of half maximum (FWHM) of the emission wavelength spectrum of about 45 nm or less, preferably about 40 nm or less, more preferably about 30 nm or less, and in this range, color purity or color reproducibility can be improved. can In addition, since light emitted through the quantum dots is emitted in all directions, a wide viewing angle may be improved.

In addition, the shape of the quantum dot is not particularly limited to that generally used in the art, but more specifically spherical, pyramidal, multi-arm, or cubic nanoparticles, nanotubes, Nanowires, nanofibers, nanoplatelets, etc. can be used.

A quantum dot can control the color of light emitted according to the particle size, and accordingly, the quantum dot can have various emission colors such as blue, red, and green.

The light control layer CCL may include a plurality of light control units CCP1 , CCP2 , and CCP3 . The light control units CCP1 , CCP2 , and CCP3 may be spaced apart from each other.

Referring to FIG. 7 , a division pattern BMP may be disposed between the light control units CCP1 , CCP2 , and CCP3 spaced apart from each other, but the embodiment is not limited thereto. In FIG. 7 , the division pattern BMP is illustrated as non-overlapping the light control units CCP1 , CCP2 , and CCP3 , but the edges of the light control units CCP1 , CCP2 , CCP3 at least partially overlap the division pattern BMP. can do.

The light control layer CCL includes a first light control unit CCP1 including a first quantum dot QD1 that converts a first color light provided from the organic electroluminescent device ED into a second color light, and a third light of the first color. It may include a second light control unit CCP2 including the second quantum dots QD2 for converting color light, and a third light control unit CCP3 for transmitting the first color light.

In an exemplary embodiment, the first light control unit CCP1 may provide red light as the second color light, and the second light control unit CCP2 may provide green light as the third color light. The third light control unit CCP3 may transmit and provide blue light, which is the first color light provided from the organic electroluminescent device ED. For example, the first quantum dot QD1 may be a red quantum dot, and the second quantum dot QD2 may be a green quantum dot. The same contents as described above may be applied to the quantum dots QD1 and QD2.

In addition, the light control layer CCL may further include a scatterer SP. The first light control unit CCP1 includes a first quantum dot QD1 and a scatterer SP, and the second light control unit CCP2 includes a second quantum dot QD2 and a scatterer SP, and the third The light control unit CCP3 may not include quantum dots and may include a scatterer SP.

The scatterers SP may be inorganic particles. For example, the scatterer SP may include at least one of TiO ₂ , ZnO, Al ₂ O ₃ , SiO ₂ , and hollow silica. The scatterers (SP) are TiO ₂ , ZnO, Al ₂ O ₃ , SiO ₂ , and any one of hollow silica, or TiO ₂ , ZnO, Al ₂ O ₃ , SiO ₂ , and hollow silica selected from It may be a mixture of two or more substances.

The light control layer CCL may include a barrier layer BFL1 . The barrier layer BFL1 may serve to prevent penetration of moisture and/or oxygen (hereinafter, referred to as 'moisture/oxygen'). The barrier layer BFL1 may be disposed on the light control units CCP1 , CCP2 , and CCP3 to block the light control units CCP1 , CCP2 , and CCP3 from being exposed to moisture/oxygen. Meanwhile, the barrier layer BFL1 may cover the light control units CCP1 , CCP2 , and CCP3 . Also, a barrier layer BFL2 may be provided between the light control units CCP1 , CCP2 , and CCP3 and the color filter layer CFL.

The barrier layers BFL1 and BFL2 may include at least one inorganic layer. That is, the barrier layers BFL1 and BFL2 may include an inorganic material. For example, the barrier layers BFL1 and BFL2 may be formed of silicon nitride, aluminum nitride, zirconium nitride, titanium nitride, hafnium nitride, tantalum nitride, silicon oxide, aluminum oxide, titanium oxide, tin oxide, cerium oxide, and silicon oxynitride or photonic acid. It may be formed by including a metal thin film, etc. having a secure transmittance. Meanwhile, the barrier layers BFL1 and BFL2 may further include an organic layer. The barrier layers BFL1 and BFL2 may be formed of a single layer or a plurality of layers.

In the display device DD according to an exemplary embodiment, the color filter layer CFL may be disposed on the light control layer CCL. For example, the color filter layer CFL may be directly disposed on the light control layer CCL. In this case, the barrier layer BFL2 may be omitted.

The color filter layer CFL may include a light blocking part BM and filters CF-1, CF-2, and CF-3. The color filter layer CFL may include a first filter CF1 that transmits the second color light, a second filter CF2 that transmits the third color light, and a third filter CF3 that transmits the first color light. . For example, the first filter CF1 may be a red filter, the second filter CF2 may be a green filter, and the third filter CF3 may be a blue filter. Each of the filters CF1, CF2, and CF3 may include a polymer photosensitive resin and a pigment or dye. The first filter CF1 may include a red pigment or dye, the second filter CF2 may include a green pigment or dye, and the third filter CF3 may include a blue pigment or dye. Meanwhile, the embodiment is not limited thereto, and the third filter CF3 may not include a pigment or dye. The third filter CF3 may include a polymer photosensitive resin and may not include a pigment or dye. The third filter CF3 may be transparent. The third filter CF3 may be formed of a transparent photosensitive resin.

Also, in an embodiment, the first filter CF1 and the second filter CF2 may be yellow filters. The first filter CF1 and the second filter CF2 are not separated from each other and may be provided integrally.

The light blocking part BM may be a black matrix. The light blocking part BM may include an organic light blocking material including a black pigment or a black dye, or an inorganic light blocking material. The light blocking part BM may prevent a light leakage phenomenon and divide a boundary between the adjacent filters CF1 , CF2 , and CF3 . Also, in an embodiment, the light blocking part BM may be formed of a blue filter.

Each of the first to third filters CF1 , CF2 , and CF3 may be disposed to correspond to each of the red emission region PXA-R, the green emission region PXA-G, and the blue emission region PXA-B. .

A base substrate BL may be disposed on the color filter layer CFL. The base substrate BL may be a member that provides a base surface on which the color filter layer CFL and the light control layer CCL are disposed. The base substrate BL may be a glass substrate, a metal substrate, a plastic substrate, or the like. However, the embodiment is not limited thereto, and the base substrate BL may be an inorganic layer, an organic layer, or a composite material layer. Also, unlike illustrated, in an exemplary embodiment, the base substrate BL may be omitted.

8 is a cross-sectional view illustrating a portion of a display device according to an exemplary embodiment. FIG. 8 is a cross-sectional view of a portion corresponding to the display panel DP of FIG. 7 . In the display device DD-TD according to an exemplary embodiment, the organic electroluminescent device ED-BT may include a plurality of light-emitting structures OL-B1 , OL-B2 , and OL-B3 . The organic electroluminescent device (ED-BT) is provided by being sequentially stacked in the thickness direction between the first electrode EL1 and the second electrode EL2 and the first electrode EL1 and the second electrode EL2 facing each other It may include a plurality of light emitting structures OL-B1, OL-B2, and OL-B3. Each of the light emitting structures OL-B1 , OL-B2 , and OL-B3 includes an emission layer EML ( FIG. 7 ), a hole transport region HTR and an electron transport region ( FIG. 7 ) disposed with the emission layer EML ( FIG. 7 ) interposed therebetween. ETR) may be included.

That is, the organic electroluminescent device ED-BT included in the display device DD-TD according to an exemplary embodiment may be an organic electroluminescent device having a tandem structure including a plurality of light emitting layers.

In the embodiment shown in FIG. 8 , all of the light emitted from each of the light emitting structures OL-B1 , OL-B2 , and OL-B3 may be blue light. However, the embodiment is not limited thereto, and wavelength ranges of light emitted from each of the light emitting structures OL-B1 , OL-B2 , and OL-B3 may be different from each other. For example, an organic electroluminescent device ED-BT including a plurality of light emitting structures OL-B1 , OL-B2 , and OL-B3 emitting light of different wavelength ranges may emit white light. .

Charge generation layers CGL1 and CGL2 may be disposed between the adjacent light emitting structures OL-B1 , OL-B2 , and OL-B3 . The charge generation layers CGL1 and CGL2 may include a p-type charge generation layer or an n-type charge generation layer.

Hereinafter, the present invention will be described in more detail through specific examples and comparative examples. The following examples are only examples to help the understanding of the present invention, and the scope of the present invention is not limited thereto.

[Example]

1. Synthesis of polycyclic compounds

First, the synthesis method of the polycyclic compound according to the present embodiment will be described in detail by exemplifying the synthesis methods of Compound 1, Compound 2, Compound 3, Compound 89, Compound 411, Compound 249, and Compound 331 of Compound Group 1. . In addition, the method for synthesizing a polycyclic compound described below is an example, and the method for synthesizing a polycyclic compound according to an embodiment of the present invention is not limited to the following examples.

<Synthesis of Compound 1>

Polycyclic Compound 1 according to an embodiment may be synthesized, for example, by the steps of Scheme 1 below.

[Scheme 1]

(1) Synthesis of compound A

로 6시간 반응시켰다. 냉각해 물을 더하여, Celite로 여과해 분액한 후, 유기층을 농축했다. Silica gel column chromatography로 정제해 화합물 A (33.1g, 수율 80%)를 얻었다. FAB MS 측정에서 화합물 A의 분자량은 447이었다. Under Ar atmosphere, 1,3-dibromo-5-chlorobenzene (25.0 g, 92.5 mmol) and Diphenylamine (31.3 g, 185 mmol), Tris (dibenzylideneacetone) dipalladium (0) - chloroform adduct (Pd ₂ (dba) ₃ CHCl ₃ , 1.78g, 1.94mmol), 2-Dicyclohexylphosphino -2',6'-dimethoxybiphenyl (SPhos, 1.59g, 3.88mmol), and tBuONa (27.1g, 282mmol) were added to 400 ml of Toluene, 80

was reacted for 6 hours. After cooling, water was added, and the mixture was separated by filtration with Celite, and the organic layer was concentrated. Purification by silica gel column chromatography gave compound A (33.1 g, yield 80%). The molecular weight of Compound A was 447 as determined by FAB MS.

(2) Synthesis of compound B

로 2시간 가열 교반했다. 물을 더하여 Celite 여과해 분액하여, 유기층을 농축했다. Silica gel column chromatography로 정제해 화합물 B (28.0 g, 수율 65%)를 얻었다. FAB MS 측정에서 화합물 B의 분자량은 745이었다. Under Ar atmosphere, compound A (33.0 g, 73.8 mmol) and compound F (12.5 g, 73.8 mmol), Pd(dba) ₂ (1.54 g, 2.68 mmol), P(t-Bu) ₃ HBF ₄ (1.56 g, 5.40 mmol), tBuONa (9.68 g, 100 mmol) was added to 300 ml of Toluene, 80

was heated and stirred for 2 hours. Water was added, the mixture was separated by Celite filtration, and the organic layer was concentrated. Purification by silica gel column chromatography gave compound B (28.0 g, yield 65%). The molecular weight of compound B was 745 as determined by FAB MS.

(3) Synthesis of compound C

로 2시간 가열 교반했다. 물을 더하여 Celite 여과해 분액하여, 유기층을 농축했다. Silica gel column chromatography로 정제해 화합물 C (74.6 g, 수율 88%)를 얻었다. FAB MS 측정에서 화합물 C의 분자량은 FAB MS 측정에서 화합물 C의 분자량은 583이었다. Under Ar atmosphere, 1,3-dibromo-5-fluorobenzene (50.0 g, 197 mmol) and N-phenyl-biphenyl-2-amine (70.0 g, 414 mmol), Pd(dba) ₂ (5.66 g, 9.85 mmol), P (t-Bu) ₃ HBF ₄ (2.86 g, 9.85 mmol) and tBuONa (66.2 g, 689 mmol) were added to 700 ml of Toluene, 80

was heated and stirred for 2 hours. Water was added, the mixture was separated by Celite filtration, and the organic layer was concentrated. Purification by silica gel column chromatography gave compound C (74.6 g, yield 88%). The molecular weight of Compound C as measured by FAB MS was 583 as the molecular weight of Compound C as measured by FAB MS.

(4) Synthesis of compound D

로 10시간 가열 교반했다. 냉각해, 물과 Toluene을 더하여, 분액해, 유기층을 농축했다. Silica gel column chromatography로 정제해 화합물 D (19.3g, 수율 60%)를 얻었다. FAB MS 측정에서 화합물 D의 분자량은 707이었다. In Ar atmosphere, compound C (25.0g, 58.0mmol), 3-chlorobenzenethiol (10.9g, 75.5mmol), K ₃ PO ₄ (49.3g, 232mmol) was added to 1-Methyl-2-pyrrolidone (NMP, 250ml) , 170

was heated and stirred for 10 hours. It cooled, water and Toluene were added, liquid-separated, and the organic layer was concentrated. Purification by silica gel column chromatography gave compound D (19.3 g, yield 60%). The molecular weight of compound D was 707 in FAB MS measurement.

(5) Synthesis of compound E

The synthesis of compound E was carried out in the same manner as the synthesis of compound B, and compound E (29.7 g, yield 79%) was obtained from compound D (19.0 g, 34.2 mmol) and compound B (15.3 g, 34.2 mmol). The molecular weight of compound E was 1416 as determined by FAB MS.

(6) Synthesis of compound 1

로 10시간 가열 교반했다. 실온까지 냉각해, N,N-Diisopropylethylamine (110g, 851 mmol)을 더하여, 물을 더하여, Celite 여과해 분액하여, 유기층을 농축했다. Silica gel column chromatography로 정제해 화합물 1 (8.82 g, 수율 30%)을 얻었다. FAB MS 측정에서 화합물 1의 분자량은 1431였다. 승화 정제(395

, 7.5Х10^-3Pa)해 디바이스 평가를 실시하였다.In an Ar atmosphere, compound E (29.0 g, 26.4 mmol) was dissolved in 1,2-Dichlorobenzene (ODCB, 380 ml), and BBr ₃ (39.7 g, 158 mmol) was added, 180

was heated and stirred for 10 hours. After cooling to room temperature, N,N-Diisopropylethylamine (110 g, 851 mmol) was added, water was added, the mixture was separated by Celite filtration, and the organic layer was concentrated. Purification by silica gel column chromatography gave compound 1 (8.82 g, yield 30%). In FAB MS measurement, the molecular weight of compound 1 was 1431. Sublimation Refining (395

, 7.5Х10 ^-3 Pa) to evaluate the device.

<Synthesis of compound 2>

Polycyclic Compound 2 according to an embodiment may be synthesized, for example, by the steps of Scheme 2 below.

[Scheme 2]

(1) Synthesis of compound F

The synthesis of compound F was carried out in the same manner as in the synthesis of compound B, to obtain compound F (20.0 g, yield 85%). The molecular weight of compound F was 636 as determined by FAB MS.

The synthesis of compound H was carried out in the same manner as that of compound B, and compound H (21.0 g, yield 76%) was obtained from compound G (13.4 g, 24.1 mmol) and compound F (15.3 g, 24.1 mmol). The molecular weight of compound H was 1154 as determined by FAB MS.

(2) Synthesis of compound 2

The synthesis of compound 2 was carried out in the same manner as in the synthesis of compound 1, to obtain compound 2 (4.1 g, yield 20%) from compound H (20.0 g, 17.3 mmol). In FAB MS measurement, the molecular weight of Compound 2 was 1170. Sublimation purification (390°C, 6.5×10 ⁻³ Pa) was performed to evaluate the device.

<Synthesis of compound 3>

Polycyclic compound 3 according to an embodiment may be synthesized, for example, by the steps of Scheme 3 below.

[Scheme 3]

(1) Synthesis of compound I

The synthesis of compound I was carried out in the same manner as the synthesis of compound B, to obtain compound I (30.0 g, yield 82%). The molecular weight of compound I was 655 by FAB MS measurement.

(2) Synthesis of compound J

In an Ar atmosphere, compound I (28.0 g, 42.7 mmol), 1-fluoro-3-iodobenzene (75.8 g, 341.5 mmol), CuI (8.1 g, 42.7 mmol), and K ₂ CO ₃ (29.5 g, 213 mmol) were 190 The mixture was heated and stirred at °C for 72 hours. After cooling, toluene and water were added, filtered through Celite, and the organic layer was concentrated. Purification by silica gel column chromatography gave compound J (16.6 g, yield 52%). The molecular weight of compound J was 749 as determined by FAB MS.

(3) Synthesis of compound K

The synthesis of compound K was carried out in the same manner as that of compound D, and compound K (19.1 g, yield 62%) was obtained from compound J (25.0 g, 33.3 mmol) and 3,5-dichlorobenzenethiol (7.76 g, 43.3 mmol). got it The molecular weight of compound K was 908 as determined by FAB MS.

(4) Synthesis of compound L

The synthesis of compound L was carried out in the same manner as the synthesis of compound C, and compound K (22.1 g, yield 90%) was obtained from compound K (19.0 g, 20.9 mmol) and diphenylamine (7.42 g, 43.9 mmol). The molecular weight of compound L was 1174 as determined by FAB MS.

(5) Synthesis of compound 3

The synthesis of compound 3 was carried out in the same manner as in the synthesis of compound 1, to obtain compound 3 (3.34 g, yield 15%) from compound L (22.0 g, 18.7 mmol). In FAB MS measurement, the molecular weight of compound 3 was 1190. The device was evaluated by sublimation purification (395°C, 8.8×10 ^-3 Pa).

<Synthesis of compound 89>

Polycyclic compound 89 according to an embodiment may be synthesized, for example, by the steps of Scheme 4 below.

[Scheme 4]

(1) Synthesis of compound M

The synthesis of compound M was carried out in the same way as the synthesis of compound C, and compound M (33.2 g, yield 91%) was obtained from 1-bromo-3,5-difluorobenzene (25.0 g, 129 mmol) and diphenylamine (24.1 g, 142 mmol). got The molecular weight of compound M was 281 as determined by FAB MS.

(2) Synthesis of compound N

The synthesis of compound N was carried out in the same manner as the synthesis of compound D, and compound N (20.7 g, yield 64%) was obtained from compound M (25.0 g, 88.8 mmol) and Phenol (10.9 g, 115 mmol). The molecular weight of compound N was 355 as determined by FAB MS.

(3) Synthesis of compound O

The synthesis of compound O was carried out in the same manner as the synthesis of compound D, to obtain compound O (21.6 g, yield 80%) from compound N (20.0 g, 56.3 mmol). The molecular weight of O was 480 in FAB MS measurement.

(3) Synthesis of compound P

The synthesis of compound P was carried out in the same manner as in the synthesis of compound H, to obtain compound P (33.6 g, yield 75%) from compound O (21.0 g, 43.8 mmol). The molecular weight of compound P was 1023 as determined by FAB MS.

(4) Synthesis of compound 89

The synthesis of compound 89 was carried out in the same manner as in the synthesis of compound 1, to obtain compound 84 (11.7 g, yield 35%) from compound P (33.0 g, 32.3 mmol). The molecular weight of compound 83 was 1038 as determined by FAB MS. The device was evaluated by sublimation purification (395°C, 9.7×10 ^-3 Pa).

<Synthesis of compound 411>

Polycyclic compound 411 according to an embodiment may be synthesized, for example, by the steps of Scheme 5 below.

[Scheme 5]

(1) Synthesis of compound Q

The synthesis of compound Q was carried out in the same manner as the synthesis of compound D, to obtain compound Q (17.8 g, yield 54%) from compound M (25.0 g, 88.8 mmol) and thiophenol (12.7 g, 116 mmol). The molecular weight of compound Q was 371 as determined by FAB MS.

(2) Synthesis of compound R

The synthesis of compound R was carried out in the same manner as that of compound D, to obtain compound R (16.3 g, yield 72%) from compound Q (17.0 g, 45.8 mmol). The molecular weight of O was 496 in FAB MS measurement.

(3) Synthesis of compound S

The synthesis of compound S was carried out in the same manner as in the synthesis of compound H, to obtain compound S (25.8 g, yield 77%) from compound R (16.0 g, 32.2 mmol). The molecular weight of S was 1039 in FAB MS measurement.

(4) Synthesis of compound 411

The synthesis of compound 411 was carried out in the same manner as in the synthesis of compound 1, to obtain compound 411 (11.4 g, yield 45%) from compound S (25.0 g, 24.4 mmol). The molecular weight of compound 411 was 1054 as determined by FAB MS. Sublimation purification (395°C, 7.7×10 ⁻³ Pa) was performed to evaluate the device.

<Synthesis of compound 249>

Polycyclic compound 249 according to an embodiment may be synthesized, for example, by the steps of Scheme 6 below.

[Scheme 6]

(1) Synthesis of compound T

The synthesis of compound T was carried out in the same manner as in the synthesis of compound B, to obtain compound T (20.0 g, yield 80%). The molecular weight of compound T was 581 as determined by FAB MS.

(2) Synthesis of compound U

The synthesis of compound U was carried out in the same manner as that of compound J, and compound U (13.6 g, yield 65%) from compound T (18.0 g, 31.0 mmol) and 1-fluoro-3-iodobenzene (55.0 g, 248 mmol) ) was obtained. The molecular weight of compound U was 675 as determined by FAB MS.

(3) Synthesis of compound V

The synthesis of compound V was carried out in the same manner as that of compound D, and compound V (12.0 g, yield 75%) was obtained from compound U (13.0 g, 19.3 mmol) and 3,5-dichlorobenzenethiol (4.48 g, 25.0 mmol). got it The molecular weight of compound V was 834 as determined by FAB MS.

(4) Synthesis of compound W

The synthesis of compound W was carried out in the same way as the synthesis of compound C, and compound W (13.3 g, yield 92%) was obtained from compound V (11.0 g, 13.2 mmol) and diphenylamine (4.67 g, 27.7 mmol). The molecular weight of compound W was 1099 as determined by FAB MS.

(5) Synthesis of compound 249

The synthesis of compound 249 was carried out in the same manner as in the synthesis of compound 1, to obtain compound 249 (2.38 g, yield 18%) from compound W (13.0 g, 11.8 mmol). The molecular weight of compound 249 was 1115 as determined by FAB MS. The device was evaluated by sublimation purification (380°C, 7.8×10 ^-3 Pa).

<Synthesis of compound 331>

Polycyclic compound 331 according to an embodiment may be synthesized, for example, by the steps of Scheme 7 below.

[Scheme 7]

(1) Synthesis of compound X

The synthesis of compound X was carried out in the same manner as that of compound B, to obtain compound X (18.0 g, yield 72%). The molecular weight of compound X was 597 as determined by FAB MS.

(2) Synthesis of compound Y

The synthesis of compound Y was carried out in the same manner as the synthesis of compound J, and compound Y (14.7 g, yield 75%) from compound X (17.0 g, 28.5 mmol) and 1-fluoro-3-iodobenzene (50.6 g, 228 mmol) ) was obtained. The molecular weight of compound Y was 691 as determined by FAB MS.

(3) Synthesis of compound Z

The synthesis of compound Z was carried out in the same way as the synthesis of compound D, and compound Z (15.2 g, yield 88%) was obtained from compound Y (14.0 g, 20.3 mmol) and 3,5-dichlorobenzenethiol (4.72 g, 26.3 mmol). got it The molecular weight of compound Z was 850 as determined by FAB MS.

(4) Synthesis of compound AA

The synthesis of compound AA was carried out in the same manner as the synthesis of compound C, and compound AA (17.1 g, yield 87%) was obtained from compound Z (15.0 g, 17.7 mmol) and diphenylamine (6.27 g, 37.1 mmol). The molecular weight of compound AA was 1115 as determined by FAB MS.

(5) Synthesis of compound 331

The synthesis of compound 331 was carried out in the same manner as in the synthesis of compound 1, to obtain compound 331 (1.84 g, yield 11%) from compound AA (16.5 g, 14.8 mmol). The molecular weight of compound 331 was 1131 as determined by FAB MS. The device was evaluated by sublimation purification (380°C, 6.8×10 ⁻³ Pa).

2. Fabrication and evaluation of light emitting devices

(Production of light emitting element)

An organic electroluminescent device was manufactured by using the compounds of the following Examples and Comparative Examples as a light emitting layer material.

[Example compound]

[Comparative Example Compound]

After patterning ITO with a thickness of 1500 Å on a glass substrate, it was washed with ultrapure water and subjected to UV ozone treatment for 10 minutes. Thereafter, HAT-CN was deposited to a thickness of 100 Å, α-NPD was deposited to a thickness of 800 Å, and mCP was deposited to a thickness of 50 Å to form a hole transport region.

Next, when the light emitting layer was formed, the polycyclic compound of Example or the compound of Comparative Example and mCBP were co-deposited at a ratio of 1:99 to form a layer having a thickness of 200 Å.

An electron transport region was formed by forming a 300 Å-thick layer of TPBi on the light emitting layer and a 5 Å-thick layer of LiF. Next, a second electrode having a thickness of 1000 Å was formed using aluminum (Al).

(Evaluation of characteristics of organic electroluminescent devices)

The measured values according to Examples 1 to 7 and Comparative Examples 1 to 6 are shown in Table 1 below. Roll-off is expressed as (external quantum efficiency of 1 cd/m ³ )-(1000 cd/m ³ )/(external quantum efficiency of 1 cd/m ³ )×100. The maximum luminous efficiency (EQE _max1000nit ) is a value measured at 10 mA/cm ² , and the relative lifetime means a relative lifetime value when the half-life of Comparative Example 3 is 1. Emission attenuation of delayed fluorescence represents a value measured by PL (photoluminescence) of a thin film of 1% Example or Comparative Example compound: mCBP (20 nm). In addition, the inverse interterm crossover rate constant (k _RISC ) was calculated from the luminescence attenuation and luminescence quantum yield.

Element creation example Dopant k _RISC λmax roll-off EQE _max
1000nits LT50
Relative lifespan (10 ⁴ S ^-1- ) (nm) (%) (%) Example 1 One 20 461 9.1 21.2 3.8 Example 2 2 19 464 9.8 20.5 3.8 Example 3 3 35 464 8.6 22.2 4.3 Example 4 89 18 458 12.5 17.6 3.1 Example 5 411 18 456 12.0 17.8 3.2 Example 6 249 17 456 12.9 17.6 2.4 Example 7 331 19 459 9.9 20.6 2.7 Comparative Example 1 X1 0.23 457 33.2 5.4 0.3 Comparative Example 2 X2 0.55 446 30.5 7.2 0.2 Comparative Example 3 X3 5.0 467 13.5 17.4 One Comparative Example 4 X4 18 465 13.4 17.1 1.1 Comparative Example 5 X5 17 470 16.2 12.1 0.5 Comparative Example 6 X6 1.2 461 26.3 13.4 0.4

Referring to Table 1, it can be seen that Examples 1 to 7 achieve both a longer lifespan and high efficiency compared to Comparative Examples 1 to 6 at the same time.

The polycyclic compound according to an embodiment of the present invention may increase the inverse interterm crossover rate constant (k _RISC ) by introducing a sulfur atom into the core structure. In addition, Triplet-Triplet Annihilation (TTA), which is one of factors that express Roll-off, and Singlet-Triplet Annihilation by having one or more substituents at the ortho position of the phenyl group bonding to nitrogen to improve the volume of the molecule (STA) is suppressed to have a low Roll-off value. Accordingly, it can be confirmed that the polycyclic compound according to an embodiment of the present invention effectively suppresses roll-off, thereby achieving high efficiency and long life of the organic electroluminescent device.

Although the above has been described with reference to the preferred embodiment of the present invention, those skilled in the art or those having ordinary knowledge in the technical field will not depart from the spirit and technical scope of the present invention described in the claims to be described later. It will be understood that various modifications and variations of the present invention can be made without departing from the scope of the present invention.

Accordingly, the technical scope of the present invention should not be limited to the contents described in the detailed description of the specification, but should be defined by the claims.

DD, DD-TD: display device
ED: organic electroluminescent element EL1: first electrode
EL2: second electrode HTR: hole transport region
EML: light emitting layer ETR: electron transport region

Claims (20)

a first electrode;
a hole transport region provided on the first electrode;
a light emitting layer provided on the hole transport region;
an electron transport region provided on the light emitting layer; and
a second electrode provided on the electron transport region;
The light emitting layer is an organic electroluminescent device comprising a polycyclic compound represented by the following formula (1):
[Formula 1]

In Formula 1,
X ₁ and X ₂ are each independently O, S, or NR ₇ ,
e and f are each independently an integer of 0 or more and 4 or less,
g is an integer of 0 or more and 2 or less,
h is an integer of 0 or more and 3 or less,
R ₁ to R ₄ , R _5-1 to R _5-3 and R _6-1 to R _6-3 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a substituted or unsubstituted A substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted ring carbon number 2 or more and 30 or less heteroaryl group, or combine with an adjacent group to form a ring,
R ₇ is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring carbon number 2 to 30 or a heteroaryl group of, or combined with an adjacent group to form a ring,
Y ₁ , and Y ₂ are each independently each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 6 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or A substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring carbon atoms,
However, at least one of Y ₁ and Y ₂ is a substituted or unsubstituted alkyl group having 6 or more and 20 or less carbon atoms, a substituted or unsubstituted aryl group having 6 or more and 30 or less ring carbon atoms, or a substituted or unsubstituted ring carbon number 2 or more and 30 or less heteroaryl groups.
According to claim 1,
The light emitting layer is an organic electroluminescent device that emits delayed fluorescence.
According to claim 1,
The light emitting layer is a delayed fluorescent light emitting layer comprising a first compound and a second compound,
The first compound is an organic electroluminescent device comprising the polycyclic compound.
According to claim 1,
The light emitting layer is an organic electroluminescent device that is a thermally activated delayed fluorescent light emitting layer that emits light having a wavelength of 430 nm to 480 nm.
According to claim 1,
At least one of X ₁ and X ₂ is NR ₇ ,
R ₇ is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.
According to claim 1,
Formula 1 is an organic electroluminescent device represented by any one of Formulas 2-1 to 2-5:
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

In Formulas 2-1 to 2-5,
Ar _1-1 and Ar _1-2 are each independently a substituted or unsubstituted aryl group having 6 or more and 30 or less ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring carbon atoms,
R ₁ to R ₄ , R _5-1 to R _{5-3 ,} R _6-1 to R _6-3 , Y ₁ , Y ₂ , and e to h are the same as defined in Formula 1 above.
7. The method of claim 6,
The Ar _1-1 and Ar _1-2 are each independently an organic electroluminescent device represented by any one of the following Chemical Formulas 5-1 to 5-3:
[Formula 5-1]

[Formula 5-2]

[Formula 5-3]

In Formulas 5-1 to 5-3,
R _a1 to R _a5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or It is an unsubstituted heteroaryl group having 2 or more and 30 or less ring carbon atoms,
m1, m3, and m5 are each independently an integer of 0 or more and 5 or less,
m2 is an integer of 0 or more and 9 or less,
m4 is an integer of 0 or more and 3 or less.
According to claim 1,
The R _5-1 to R _5-3 , and At least one of R _6-1 to R _6-3 is a substituted amine group.
According to claim 1,
Formula 1 is an organic electroluminescent device represented by Formula 3-1 or Formula 3-2:
[Formula 3-1]

[Formula 3-2]

In Formulas 3-1 and 3-2,
Ar _{3-1 ,} Ar _3-2 , Ar _4-1 and Ar _4-2 is each independently a substituted or unsubstituted aryl group having 6 or more and 30 or less ring carbon atoms,
X ₁ , X ₂ , R ₁ to R ₄ , R _5-1 to R _{5-3 ,} R _6-1 to R _6-3 , Y ₁ , Y ₂ , and e to h are the same as defined in Formula 1 above. do.
According to claim 1,
Chemical Formula 1 is an organic electroluminescent device represented by the following Chemical Formula 4:
[Formula 4]

In Formula 4,
Ar _{3-1 ,} Ar _3-2 , Ar _4-1 and Ar _4-2 is each independently a substituted or unsubstituted aryl group having 6 or more and 30 or less ring carbon atoms,
X ₁ , X ₂ , R ₁ To R ₄ , R _5-1 , R _{5-3 ,} R _6-1 , R _6-3 , Y ₁ , Y ₂ , and e to h are the same as defined in Formula 1 above. do.
11. The method of claim 10,
Ar _3-1, Ar _3-2 , Ar _4-1 and Ar _4-2 is each independently a substituted or unsubstituted aryl group having 6 or more and 18 or less ring carbon atoms.
The method of claim 1,
The polycyclic compound represented by Formula 1 is an organic electroluminescent device which is any one of the compounds represented by the following compound group 1:
[Compound group 1]

.
A polycyclic compound represented by the following formula (1):
[Formula 1]

In Formula 1,
X ₁ and X ₂ are each independently O, S, or NR ₇ ,
e and f are each independently an integer of 0 or more and 4 or less,
g is an integer of 0 or more and 2 or less,
h is an integer of 0 or more and 3 or less,
R ₁ to R ₄ , R _5-1 to R _5-3 and R _6-1 to R _6-3 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, a substituted or unsubstituted A substituted or unsubstituted thiol group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted ring carbon number 2 or more and 30 or less heteroaryl group, or combine with an adjacent group to form a ring,
R ₇ is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring carbon number 2 to 30 or a heteroaryl group of, or combined with an adjacent group to form a ring,
Y ₁ , and Y ₂ are each independently each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 6 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or A substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring carbon atoms,
However, at least one of Y ₁ and Y ₂ is a substituted or unsubstituted alkyl group having 6 or more and 20 or less carbon atoms, a substituted or unsubstituted aryl group having 6 or more and 30 or less ring carbon atoms, or a substituted or unsubstituted ring carbon number 2 or more and 30 or less heteroaryl groups.
14. The method of claim 13,
At least one of X ₁ and X ₂ is NR ₇ ,
R ₇ is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms.
14. The method of claim 13,
Formula 1 is a polycyclic compound represented by any one of Formulas 2-1 to 2-5:
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

In Formulas 2-1 to 2-5,
Ar _1-1 and Ar _1-2 are each independently a substituted or unsubstituted aryl group having 6 or more and 30 or less ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 or more and 30 or less ring carbon atoms,
R ₁ to R ₄ , R _5-1 to R _{5-3 ,} R _6-1 to R _6-3 , Y ₁ , Y ₂ , and e to h are the same as defined in Formula 1 above.
16. The method of claim 15,
Ar _1-1 and Ar _1-2 are each independently a polycyclic compound represented by any one of Formulas 5-1 to 5-3:
[Formula 5-1]

[Formula 5-2]

[Formula 5-3]

In Formulas 5-1 to 5-3,
R _a1 to R _a5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or It is an unsubstituted heteroaryl group having 2 or more and 30 or less ring carbon atoms,
m1, m3, and m5 are each independently an integer of 0 or more and 5 or less,
m2 is an integer of 0 or more and 9 or less,
m4 is an integer of 0 or more and 3 or less.
14. The method of claim 13,
The R _5-1 to R _5-3 , and A polycyclic compound wherein at least one of R _6-1 to R _6-3 is a substituted amine group.
14. The method of claim 13,
Formula 1 is a polycyclic compound represented by Formula 3-1 or Formula 3-2:
[Formula 3-1]

[Formula 3-2]

In Formulas 3-1 and 3-2,
Ar _{3-1 ,} Ar _3-2 , Ar _4-1 and Ar _4-2 is each independently a substituted or unsubstituted aryl group having 6 or more and 30 or less ring carbon atoms,
X ₁ , X ₂ , R ₁ to R ₄ , R _5-1 to R _{5-3 ,} R _6-1 to R _6-3 , Y ₁ , Y ₂ , and e to h are the same as defined in Formula 1 above. do.
14. The method of claim 13,
Formula 1 is a polycyclic compound represented by Formula 4 below:
[Formula 4]

In Formula 4,
Ar _{3-1 ,} Ar _3-2 , Ar _4-1 and Ar _4-2 is each independently a substituted or unsubstituted aryl group having 6 or more and 30 or less ring carbon atoms,
X ₁ , X ₂ , R ₁ To R ₄ , R _5-1 , R _{5-3 ,} R _6-1 , R _6-3 , Y ₁ , Y ₂ , and e to h are the same as defined in Formula 1 above. do.
15. The method of claim 14,
The polycyclic compound represented by Formula 1 is a polycyclic compound which is any one of the compounds represented in the following compound group 1:
[Compound group 1]

.

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