CN116491242A

CN116491242A - Organic light-emitting element comprising novel organic compound in light-emitting layer

Info

Publication number: CN116491242A
Application number: CN202180078145.1A
Authority: CN
Inventors: 金是仁; 李世珍; 朴锡培; 金熙大; 崔英太; 金志泳; 金敬泰; 金明俊; 金炅铉; 李有琳; 李承受; 李泰均; 金濬镐
Original assignee: SFC Co Ltd
Current assignee: SFC Co Ltd
Priority date: 2020-11-26
Filing date: 2021-07-30
Publication date: 2023-07-25

Abstract

The present invention relates to an organic light-emitting element comprising an organic compound represented by [ chemical formula a ] or [ chemical formula B ], and more particularly, to an organic light-emitting element comprising two light-emitting layers between a first electrode and a second electrode, at least one of the two light-emitting layers using the organic compound represented by [ chemical formula a ] or [ chemical formula B ], wherein the [ chemical formula a ] and the [ chemical formula B ] are the same as those described in the detailed description of the invention.

Description

Organic light-emitting element comprising novel organic compound in light-emitting layer

Technical Field

The present invention relates to an organic light-emitting device including a novel compound usable for the organic light-emitting device in a light-emitting layer, and more particularly, to an organic light-emitting device including: the two light emitting layers are included between the first electrode and the second electrode, and by introducing the novel organic compound to at least one of the two light emitting layers, element characteristics of high light emitting efficiency, low voltage driving, and long lifetime can be achieved.

Background

An organic light emitting element (OLED: organic light emitting diode) is a display utilizing a self-luminescence phenomenon, and has advantages such as a wide viewing angle, a thin and small size, and a fast response speed, as compared with a liquid crystal display, and thus is expected to be applied as a full-color (full-color) display or illumination.

In general, the organic light emitting phenomenon means a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting element utilizing an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic layer therebetween. In many cases, the organic layer is a multilayer structure composed of substances different from each other, and may be composed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like, in order to improve efficiency and stability of the organic light emitting element. In the structure of such an organic light emitting element, if a voltage is applied between two electrodes, holes are injected from an anode to an organic layer, electrons are injected from a cathode to the organic layer, and when the injected holes and electrons meet, excitons (exiton) are formed, and light is emitted when the excitons fall back to a ground state. Such an organic light emitting element is known to have characteristics of self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, fast response, and the like.

Materials used as an organic layer in an organic light-emitting element can be classified into a light-emitting material and a charge-transporting material according to functions, for example, a hole-injecting material, a hole-transporting material, an electron-injecting material, and the like. The light emitting materials may be classified into a high molecular type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism.

Further, in the case where only one substance is used as a light emitting material, there is a problem in that the maximum emission wavelength shifts to a long wavelength due to the intermolecular interaction and the color purity decreases or the efficiency of the element decreases due to the light emission attenuation effect, so in order to improve the color purity and increase the light emission efficiency by energy transfer, a host-dopant system may be used as a light emitting material.

The principle is as follows: if a small amount of dopant smaller than the band gap of the host forming the light emitting layer is mixed in the light emitting layer, excitons generated from the light emitting layer are transferred to the dopant to emit light with high efficiency. At this time, the wavelength of the host shifts to the wavelength band of the dopant, so that light of a desired wavelength can be obtained according to the type of dopant used.

Recently, studies on heterocyclic compounds as dopant compounds in such light-emitting layers have been conducted, and as related art, a compound concerning a structure in which a dibenzofuran ring is bonded to an anthracene ring and an organic light-emitting element including the compound are described in korean laid-open patent publication No. 10-2016-0089693 (2016.07.28), and a compound in which an aromatic substituent or a heteroaromatic substituent is bonded to a condensed fluorene ring containing a heteroatom such as oxygen, nitrogen, sulfur, and an organic light-emitting element including the compound are disclosed in korean laid-open patent publication No. 10-2017-0055743 (2017.05.22).

However, even though various forms of compounds including the above-described prior art, which are used for a light emitting layer of an organic light emitting element, there is still a continuous need to develop a novel organic light emitting element which can be applied to an organic light emitting element and has element characteristics of high efficiency, low voltage driving and long life.

Disclosure of Invention

Technical problem

Accordingly, a first technical problem which the present invention is expected to solve is to provide an organic light emitting element (OLED: organic light emitting diode) with high efficiency, low voltage driving and long life by using a novel organic compound which can be used as a host substance of a light emitting layer in the organic light emitting element.

Technical proposal

In order to solve the above-described problems, the present invention provides an organic light-emitting element comprising: a first electrode; and a second electrode facing the first electrode, the second electrode including, in order between the first electrode and the second electrode: a first light emitting layer comprising a first host and a first dopant; and a second light emitting layer including a second host and a second dopant, wherein at least one of the first host and the second host includes one or more compounds represented by [ chemical formula a ] or [ chemical formula B ] described below.

In the [ chemical formula A ] and the [ chemical formula B ],

the R is ₁ To R ₁₄ And are each the same or different and are each independently selected from any one of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, a halogen group;

the linker L ₁ And L ₂ Are each identical to or different from each other and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms;

wherein n1 and n2 are the same or different, and are each independently an integer of 0 to 2, and each is 2, the linking group L ₁ And L ₂ Are the same as or different from each other,

the R and R' are the same or different and are selected from any one of hydrogen, deuterium, substituted or unsubstituted alkyl group with carbon number of 1 to 30, substituted or unsubstituted aryl group with carbon number of 6 to 50, substituted or unsubstituted cycloalkyl group with carbon number of 3 to 30, substituted or unsubstituted heterocycloalkyl group with carbon number of 2 to 30, substituted or unsubstituted heteroaryl group with carbon number of 2 to 50, substituted or unsubstituted alkylamino group with carbon number of 1 to 30, substituted or unsubstituted arylamino group with carbon number of 6 to 30, substituted or unsubstituted alkylsilyl group with carbon number of 1 to 30, substituted or unsubstituted arylsilyl group with carbon number of 6 to 30, cyano group, nitro group, halogen group;

wherein n3 and n4 are the same or different, and each is an integer of 1 to 9, independently of the other, and each is 2 or more, R and R' are the same or different from each other,

in the above-mentioned [ chemical formula a ] and [ chemical formula B ], the "substituted" in the "substituted or unsubstituted" means a sulfur substituted by one member selected from the group consisting of deuterium, cyano, halo, hydroxy, nitro, alkyl having 1 to 24 carbon atoms, haloalkyl having 1 to 24 carbon atoms, alkenyl having 1 to 24 carbon atoms, alkynyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, heteroalkyl having 1 to 24 carbon atoms, aryl having 6 to 24 carbon atoms, aralkyl having 7 to 24 carbon atoms, alkylaryl having 7 to 24 carbon atoms, heteroaryl having 2 to 24 carbon atoms, heteroaralkyl having 2 to 24 carbon atoms, alkoxy having 1 to 24 carbon atoms, alkylamino having 1 to 24 carbon atoms, diarylamino having 12 to 24 carbon atoms, diheteroarylamino having 2 to 24 carbon atoms, aryl (hetero) amino having 7 to 24 carbon atoms, alkylsilyl having 1 to 24 carbon atoms, arylsilyl having 6 to 24 carbon atoms, and aryl having 6 to 24 carbon atoms.

Technical effects

According to the present invention, there can be provided an organic light emitting element as follows: in the organic light emitting element, there are two light emitting layers, and when the organic compound represented by the chemical formula a or the chemical formula B is introduced into at least one of them, high efficiency, low voltage driving, and long life are exhibited as compared to the organic light emitting element according to the related art.

Drawings

Fig. 1 is a schematic view of an organic light emitting element according to an embodiment of the present invention.

Detailed Description

The present invention will be described in more detail below. In the drawings of the present invention, the size or dimension of the structure is shown enlarged or reduced from that of the actual structure for clarity of the present invention, and well-known structures are omitted for highlighting the characteristic structures, and therefore the present invention is not limited to the drawings.

The size and thickness of each of the components shown in the drawings are arbitrarily shown for convenience of explanation, and therefore the present invention is not necessarily limited to the content shown in the drawings, and the thicknesses are shown enlarged for clearly showing a plurality of layers and regions in the drawings. In the drawings, the thicknesses of partial layers and regions are exaggerated for convenience of explanation. When a layer, film, region, plate, or the like is referred to as being "on" another portion, it includes not only the case of being "immediately above" the other portion but also the case of having another portion in the middle.

In the present specification, when a certain component is referred to as "including" a certain component, unless otherwise specified, it means that other components are not excluded, but other components may be included. In the present specification, "on …" means above or below the target portion, and does not necessarily mean above the gravitational direction.

The present invention provides an organic light-emitting element, comprising: a first electrode; and a second electrode facing the first electrode, the second electrode including, in order between the first electrode and the second electrode: a first light emitting layer comprising a first host and a first dopant; and a second light emitting layer including a second host and a second dopant, wherein at least one of the first host and the second host includes one or more compounds represented by [ chemical formula a ] or [ chemical formula B ] described below.

In the [ chemical formula A ] and the [ chemical formula B ],

Further, considering the ranges of the alkyl or aryl groups in the "substituted or unsubstituted alkyl group having 1 to 30 carbon atoms", "substituted or unsubstituted aryl group having 5 to 50 carbon atoms" and the like in the present invention, the ranges of the alkyl group having 1 to 30 carbon atoms and the aryl group having 5 to 50 carbon atoms respectively represent: the number of carbon atoms in the whole alkyl or aryl moiety when considered unsubstituted, regardless of the moiety substituted by the substituent. For example, a phenyl group substituted with a butyl group at the para-position is considered to correspond to an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

The aryl group as a substituent used in the compound of the present invention is an organic radical derived from an aromatic hydrocarbon by removing one hydrogen, and when a substituent is present in the aryl group, substituents adjacent to each other can be condensed (fused) with each other to form a ring additionally.

Specific examples of the aryl group include phenyl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl, p-terphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, indenyl, fluorenyl, tetrahydronaphthyl, perylenyl, and, An aromatic group such as a group, a tetracenyl group, a fluoranthenyl group, or the like, wherein one or more hydrogen atoms in the aromatic group may be replaced with a deuterium atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a silyl group, an amino group (-NH) ₂ -NH (R), -N (R ') (R "), R' and R" are independently of each other alkyl of 1 to 10 carbon atoms, in this case referred to as "alkylamino"), amidino, hydrazino, hydrazone, carboxyl, sulphonic acid, phosphoric acid, alkyl of 1 to 24 carbon atoms, haloalkyl of 1 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, alkynyl of 2 to 24 carbon atoms, heteroalkyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, aralkyl of 6 to 24 carbon atoms, heteroaryl of 2 to 24 carbon atoms or heteroaralkyl of 2 to 24 carbon atoms.

Heteroaryl as substituents used in the compounds of the invention means a C2 to C24 cyclic aromatic system comprising 1, 2 or 3 heteroatoms selected from N, O, P, si, S, ge, se, te and the remaining ring-forming atoms being carbon atoms, said rings being fused to form a ring. In addition, one or more hydrogen atoms in the heteroaryl group may be substituted with the same substituent as in the case of the aryl group.

In the present invention, the aromatic heterocyclic ring means that one or more carbon atoms in the aromatic hydrocarbon ring are replaced with a heteroatom, and preferably 1 to 3 aromatic carbon atoms in the aromatic hydrocarbon ring may be replaced with one or more heteroatom selected from N, O, P, si, S, ge, se, te.

The alkyl group as a substituent for removing one hydrogen in the alkane (alkine) used in the present invention is a structure including a straight chain type, a branched chain type, and specific examples thereof may be methyl group, ethyl group, propyl group, isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, isopentyl group, hexyl group, etc., and one or more hydrogen atoms in the alkyl group may be substituted with the same substituent as in the case of the aryl group.

The "ring" in the cycloalkyl group as a substituent used in the compound of the present invention means a substituent that can form a monocyclic or polycyclic structure of a saturated hydrocarbon in an alkyl group, and for example, specific examples of the cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, methylcyclohexyl, ethylcyclopentyl, ethylcyclohexyl, adamantyl, biscyclopentadienyl, decahydronaphthyl, norbornyl, icyl, isobornyl and the like, and one or more hydrogen atoms in the cycloalkyl group may be substituted with the same substituent as in the case of the aryl group.

The alkoxy group of the substituent used in the compound of the present invention as a substituent having an oxygen atom bonded to the end of the alkyl group or cycloalkyl group may specifically be exemplified by methoxy group, ethoxy group, propoxy group, isobutoxy group, sec-butoxy group, pentyloxy group, isopentyloxy group, hexyloxy group, cyclobutoxy group, cyclopentyloxy group, adamantyloxy group, dicyclopentadienyloxy group, bornyloxy group, isobornyloxy group and the like, and one or more hydrogen atoms in the alkoxy group may be substituted with the same substituent as in the case of the aryl group.

Specific examples of the aralkyl group as a substituent used in the compound of the present invention may include benzyl (benzyl), phenethyl, phenylpropyl, naphthylmethyl, naphthylethyl, and the like, and one or more hydrogen atoms in the aralkyl group may be substituted with the same substituent as in the case of the aryl group.

Specific examples of the silyl group as a substituent used in the compound of the present invention may include a trimethylsilyl group, a triethylsilyl group, a triphenylsilyl group, a trimethoxysilyl group, a dimethoxyphenylsilyl group, a diphenylmethylsilyl group, a diphenylvinylsilyl group, a methylcyclobutylsilyl group, a dimethylfuranylsilyl group, and the like, and one or more hydrogen atoms in the silyl group may be substituted with the same substituent as in the case of the aryl group.

Further, in the present invention, alkenyl (alkinyl) represents an alkyl substituent including one carbon-carbon double bond composed of two carbon atoms, and alkynyl (alkinyl) represents an alkyl substituent including one carbon-carbon triple bond composed of two carbon atoms.

Further, alkylene (alkylene) groups used in the present invention are organic radicals derived by removing two hydrogens in an alkane (alkine) molecule of a saturated hydrocarbon in a straight-chain type or branched-chain type form, and specific examples of the alkylene groups may include methylene, ethylene, propylene, isopropylene, isobutylene, sec-butylene, tert-butylene, pentylene, isopentylene, hexylene, and the like, and one or more hydrogen atoms in the alkylene groups may be substituted with the same substituent as in the case of the aryl group.

In addition, in the present invention, a diarylamino group represents an amine group in which a nitrogen atom is bonded to two aryl groups which are the same or different from the above, and a diheteroarylamino group in the present invention represents an amine group in which a nitrogen atom is bonded to two heteroaryl groups which are the same or different from each other, and the aryl (heteroaryl) amino group represents an amine group in which the aryl group and the heteroaryl group are bonded to a nitrogen atom, respectively.

In addition, as preferable examples of the "substituted" in the "substituted or unsubstituted" in the [ chemical formula a ] and the [ chemical formula B ], it may be a case where an aryl group having 6 to 18 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, an alkylaryl group having 7 to 20 carbon atoms, an heteroaryl group having 2 to 20 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkylamino group having 1 to 12 carbon atoms, a diarylamino group having 12 to 18 carbon atoms, a diheteroarylamino group having 2 to 18 carbon atoms, an aryl group having 7 to 18 carbon atoms (heteroaryl group having 1 to 18 carbon atoms), an aryl group having 6 to 18 carbon atoms, an arylsilyl group having 6 to 18 carbon atoms, an oxysulfide group having 6 to 18 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkylamino group having 1 to 12 carbon atoms, a diarylamino group having 12 to 18 carbon atoms, a diarylamino group having 2 to 18 carbon atoms, an aryl group having 7 to 18 carbon atoms, an aryl group having 6 to 18 carbon atoms, an alkylsilyl group having 6 to 18 carbon atoms, an oxygen group having 6 to 18 carbon atoms.

In the present invention, the compound represented by the formula [ formula A ] ]And [ formula B ]]The organic compound represented by the formula A is a compound serving as a host in the light-emitting layer]The organic compound is characterized in that a linker L is bonded to a specific position (see the following structural formula C) in a substituted or unsubstituted pyrene ring ₁ At the linker L ₁ Position 1 to which a substituted or unsubstituted dibenzofuranyl group is bonded, and is represented by the [ formula B ]]The organic compound is characterized in that a linker L is bonded to a specific position (see the following structural formula C) in a substituted or unsubstituted pyrene ring ₂ At the linker L ₂ Position 2 to which a substituted or unsubstituted dibenzofuranyl group is bonded.

[ Structure C ]

With a linker L ₁ Or a linker L ₂ Binding sites for binding

In the [ chemical formula a ] and [ chemical formula B ] in the organic light emitting element according to the present invention, the compound represented by the chemical formula a may contain at least one deuterium, and the compound represented by the chemical formula B may contain at least one deuterium.

In more detail, the [ formula A ]]R in (a) ₁ To R ₇ At least one of which may be a substituent comprising deuterium, said [ formula B ]]R in (a) ₈ To R ₁₄ At least one of which may be a substituent comprising deuterium.

Further, in the organic light emitting element according to the present invention, the compound represented by the chemical formula a may contain at least one deuterium, in the case where the compound represented by the chemical formula B may contain at least one deuterium, at least one R in the [ chemical formula a ] may be a substituent containing deuterium, and at least one R' in the [ chemical formula B ] may be a substituent containing deuterium.

Furthermore, as an embodiment according to the present invention, the R ₁ To R ₁₄ R, R' may be the same or different, and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 18 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 15 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, and a substituent in a halogen group.

Furthermore, as an embodiment according to the present invention, the [ formula A ] ]R in (a) ₁ To R ₇ At least one of which may be a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, said [ formula B ]]R in (a) ₈ To R ₁₄ May be a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.

Furthermore, as an embodiment according to the present invention, the linking group L in the chemical formula A and the chemical formula B ₁ And L ₂ May be a single bond, or may be a member selected from the group consisting of the following structural formula 1]To [ Structure 5]]Any one of the above.

The carbon position of the aromatic ring in the [ structural formula 1] to [ structural formula 5] may be bonded with hydrogen or deuterium.

Furthermore, as an embodiment according to the present invention, the linking group L ₁ And L ₂ May each be a single bond.

Further, as an embodiment according to the present invention, the n3 and n4 in the chemical formula a and chemical formula B may be 1, respectively.

Further, as an embodiment according to the present invention, at least one R in the [ chemical formula a ] may be a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and at least one R 'in the [ chemical formula B ] may be a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, in which case, preferably, the n3 and n4 in the chemical formulas a and B are each 1, R in the [ chemical formula a ] may be a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, and R' in the [ chemical formula B ] may be a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.

Further, as an embodiment according to the present invention, the organic compound represented by the [ chemical formula a ] or the [ chemical formula B ] may be a compound represented by any one of the following [ chemical formula a-1] or [ chemical formula B-1 ].

At this time, in the [ chemical formula A-1]]And [ formula B-1]]In the above formula, the substituent R ₁ To R ₁₄ Linker L ₁ And L ₂ N1 and n2 and the preceding [ formula A ]]Or [ formula B ]]The content defined in (a) is the same,

the substituents R and R' are substituted or unsubstituted aryl groups having 6 to 18 carbon atoms.

Further, as an embodiment according to the present invention, the n3 and n4 in the chemical formula a and chemical formula B may be 1, respectively, the [ chemical formula a]R in (a) ₁ To R ₇ At least one of R may be an aryl group having 6 to 18 carbon atoms substituted with deuterium, said [ formula B ]]R in (a) ₈ To R ₁₄ At least one of R' may be an aryl group having 6 to 18 carbon atoms substituted with deuterium.

Further, as an embodiment according to the present invention, the n3 and n4 in the chemical formula a and the chemical formula B may be 1, respectively, R in the [ chemical formula a ] may be a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms, and R' in the [ chemical formula B ] may be a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms.

Further, the compound represented by the [ chemical formula a ] or [ chemical formula B ] according to the present invention may be any one compound selected from chemical formulas 1 to 240.

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In addition, in the present invention, "(organic layer) containing one or more organic compounds" can be interpreted as "(organic layer) may contain one organic compound belonging to the scope of the present invention or two or more compounds different from each other belonging to the scope of the organic compounds.

At this time, the organic layer in the organic light emitting element of the present invention may include at least one of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, a light emitting layer, an electron transport layer, and an electron injection layer.

Further, the present invention may provide an organic light emitting element as follows: at least one of a hole transporting layer and a hole injecting layer may be provided between the first electrode and the first light emitting layer, and at least one of an electron transporting layer and an electron injecting layer may be provided between the second light emitting layer and the second electrode, and preferably, the hole transporting layer and the hole injecting layer are provided between the first electrode and the first light emitting layer, respectively, and the electron transporting layer and the electron injecting layer are provided between the second light emitting layer and the second electrode, respectively.

Further, in the organic light emitting element according to the present invention, at least one of the first dopant in the first light emitting layer or the second dopant in the second light emitting layer may contain at least one compound represented by any one of the following [ chemical formula D1] to [ chemical formula D10], and preferably, the first dopant in the first light emitting layer and the second dopant in the second light emitting layer may each be the same or different and use a compound selected from any one or more of the [ chemical formula D1] to [ chemical formula D10 ].

[ chemical formula D1]

[ chemical formula D2]

In said [ chemical formula D1]]And [ chemical formula D2]]In (A) ₃₁ 、A ₃₂ 、E ₁ F (F) ₁ Are each the same or different and are each, independently of one another, a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 40 carbon atoms;

the A is ₃₁ Two carbon atoms adjacent to each other in the aromatic ring of (A) and the A ₃₂ Two carbon atoms adjacent to each other in the aromatic ring of (a) and attached to the substituent R ₅₁ And R is ₅₂ Forming five-membered rings from carbon atoms of (2) to form condensed rings, respectively;

the linker L ₂₁ To L ₃₂ And are each the same or different and are each independently selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynylene group having 2 to 60 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 60 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;

The W and W' are the same or different and are each independently selected from N-R ₅₃ 、CR ₅₄ R ₅₅ 、SiR ₅₆ R ₅₇ 、GeR ₅₈ R ₅₉ Either one of O, S, se;

the substituent R ₅₁ To R ₅₉ 、Ar ₂₁ To Ar ₂₈ Are each the same or different and are each independently selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, and a substituted or unsubstituted alkenyl groupA substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted germanium group having 1 to 30 carbon atoms, a cyano group, a nitro group having 1 to 30 carbon atoms,

The R is ₅₁ And R is ₅₂ Can be linked to each other to form an alicyclic, aromatic, single ring or multiple ring, wherein the carbon atoms of the alicyclic, aromatic, single ring or multiple ring can be substituted by one or more hetero atoms selected from N, O, P, si, S, ge, se, te;

the p11 to p14, r11 to r14 and s11 to s14 are integers from 1 to 3, respectively, and the respective linking groups L in the case where they are each 2 or more ₂₁ To L ₃₂ Are the same as or different from each other,

the x1 is 1, y1, z1 and z2 are each the same or different and are each independently an integer from 0 to 1,

the Ar is as follows ₂₁ And Ar is a group ₂₂ 、Ar ₂₃ And Ar is a group ₂₄ 、Ar ₂₅ And Ar is a group ₂₆ Ar, ar ₂₇ And Ar is a group ₂₈ Respectively, can be connected to each other to form a ring;

in the chemical formula D1, A ₃₂ Two carbon atoms adjacent to each other in the ring may be of the formula Q ₁₁ Is combined to form a condensed ring,

at the said meltingIn the chemical formula D2, the A ₃₁ Two carbon atoms adjacent to each other in the ring may be of the formula Q ₁₂ To form a condensed ring, said A ₃₂ Two carbon atoms adjacent to each other in the ring may be of the formula Q ₁₁ Is combined to form a condensed ring.

[ chemical formula D3]

In the above-mentioned [ chemical formula D3],

the X is ₁ Is any one selected from B, P, P =o,

the T1 to T3 are each the same as or different from each other and are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 40 carbon atoms;

The Y is ₁ Is selected from N-R ₆₁ 、CR ₆₂ R ₆₃ 、O、S、SiR ₆₄ R ₆₅ Any one of the following;

the Y is ₂ Is selected from N-R ₆₆ 、CR ₆₆ R ₆₈ 、O、S、SiR ₆₉ R ₇₀ Any one of the following;

the R is ₆₁ To R ₇₀ Are each identical to or different from each other and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 5 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 30 carbon atomsAn alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a cyano group, a halogen group, or a salt thereof, wherein R is ₆₁ To R ₇₀ Each of which can be bonded to one or more rings selected from the group consisting of T1 to T3 to additionally form an alicyclic or aromatic monocyclic ring or polycyclic ring.

In the [ chemical formula D4] and the [ chemical formula D5],

the X is ₂ Is any one selected from B, P, P =o,

t4 to T6 are the same as T1 to T3 in [ formula D3],

the Y is ₄ Is selected from N-R ₆₁ 、CR ₆₂ R ₆₃ 、O、S、SiR ₆₄ R ₆₅ Any one of the following;

the Y is ₅ Is selected from N-R ₆₆ 、CR ₆₆ R ₆₈ 、O、S、SiR ₆₉ R ₇₀ Any one of the following;

the Y is ₆ Is selected from N-R ₇₁ 、CR ₇₂ R ₇₃ 、O、S、SiR ₇₄ R ₇₅ Any one of the following;

the R is ₆₁ To R ₇₅ And [ chemical formula D3]]Said R in (a) ₆₁ To R ₇₀ The same applies.

The X is ₃ Is any one selected from B, P, P =o,

t7 to T9 are the same as T1 to T3 in [ formula D3],

the Y is ₆ Is selected from N-R ₆₁ 、CR ₆₂ R ₆₃ 、O、S、SiR ₆₄ R ₆₅ Any one of the following;

the substituent R ₆₁ To R ₆₅ 、R ₇₁ R is R ₇₂ Respectively with [ chemical formula D3]]Said R in (a) ₆₁ To R ₇₀ The same is true of the fact that,

the R is ₇₁ R is R ₇₂ Can be linked to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring, or can be combined with the T7 ring or the T9 ring to additionally form an alicyclic or aromatic monocyclic or polycyclic ring, respectively.

In the [ chemical formula D8] to [ chemical formula D10],

wherein X is any one selected from B, P, P =o,

the Q is ₁ To Q ₃ Respectively with [ chemical formula D3]]In (2) are the same as T1 to T3,

the linker Y is selected from N-R ₃ 、CR ₄ R ₅ Either one of the first and second films O, S, se,

the substituent R ₃ To R ₅ Respectively with [ chemical formula D3]]Said R in (a) ₆₁ To R ₇₀ The same is true of the fact that,

the R is ₃ To R ₅ Can be respectively with the Q ₂ Ring or Q ₃ The rings combine to additionally form a single or multiple ring that is alicyclic or aromatic,

the R is ₄ And R is ₅ Can be linked to each other to additionally form a single or multiple ring of alicyclic or aromatic nature,

if the ring formed by the Cy1 removes a nitrogen (N) atom, Q bonded with the nitrogen (N) atom ₁ An intra-ring aromatic carbon atom and Q to be bonded to the Cy1 ₁ An intra-ring aromatic carbon atom, the balance being a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms,

in the chemical formula D9 of the present invention,

the "Cy2" can be attached to the Cy1 to form a saturated hydrocarbon ring, and if the carbon atom contained in Cy1 is removed from the ring formed by the Cy2, the remainder is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms,

in the chemical formula D10 described above, the chemical formula,

the ring formed by the Cy3 if removed will bind Q to the Cy3 ₃ An aromatic carbon atom in the ring, Q to be bonded to a nitrogen (N) atom ₃ An internal aromatic carbon atom, a nitrogen (N) atom, a Cy1 internal carbon atom to which the nitrogen (N) atom is bonded, the remainder being a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms,

wherein the "substituted" in the "substituted or unsubstituted" in the [ chemical formula D1] to [ chemical formula D10] means a sulfur-substituted aryl group having 6 to 24 carbon atoms, an aralkyl group having 7 to 24 carbon atoms, an alkylaryl group having 7 to 24 carbon atoms, an heteroaryl group having 7 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, a diarylamino group having 12 to 24 carbon atoms, a diheteroarylamino group having 2 to 24 carbon atoms, an aryl (hetero) group having 7 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, a sulfur-substituted aryl group having 6 to 24 carbon atoms, as more preferable examples, it may be a deuterium, cyano, halo, hydroxy, nitro, alkyl having 1 to 12 carbon atoms, haloalkyl having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, alkynyl having 2 to 12 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, heteroalkyl having 1 to 12 carbon atoms, aryl having 6 to 18 carbon atoms, aralkyl having 7 to 20 carbon atoms, alkylaryl having 7 to 20 carbon atoms, heteroaryl having 2 to 18 carbon atoms, A heteroarylalkyl group having 2 to 18 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkylamino group having 1 to 12 carbon atoms, a diarylamino group having 12 to 18 carbon atoms, a diheteroarylamino group having 2 to 18 carbon atoms, an aryl (heteroaryl) amino group having 7 to 18 carbon atoms, an alkylsilyl group having 1 to 12 carbon atoms, an arylsilyl group having 6 to 18 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, or an arylsulfinyl group having 6 to 18 carbon atoms.

Furthermore, the dopant compound according to the invention is represented by the [ formula D3 ]]To [ chemical formula D10 ]]In the case where the compound represented by any one of the above is a boron compound, the compound may be substituted for the above-mentioned T1 to T9 or Q ₁ To Q ₃ The substituent of the aromatic hydrocarbon ring or the aromatic heterocyclic ring of (a) may be deuterium, an alkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 6 to 24 carbon atoms, wherein the alkyl group or the aryl group of each of the alkylamino group having 1 to 24 carbon atoms and the arylamino group having 6 to 24 carbon atoms may be bonded to each other, and as a more preferable substituent, an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, an alkylamino group having 1 to 12 carbon atoms, an arylamino group having 6 to 18 carbon atoms, and the alkyl group or the aryl group of each of the alkylamino group having 1 to 12 carbon atoms and the arylamino group having 6 to 18 carbon atoms may be bonded to each other.

In addition, in the dopant compound for the light-emitting layer in the organic light-emitting element according to the present invention, as a specific example of the compound represented by any one of the [ chemical formula D1] to [ chemical formula D2], a compound represented by any one of the following < D1> to < D239> may be mentioned.

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In the present invention, the compound represented by [ chemical formula D3] in the dopant compound in the light-emitting layer may be a compound represented by any one selected from the following < D101> to < D130 >.

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Further, in the present invention, the compound represented by any one of the [ chemical formula D4], [ chemical formula D5], [ chemical formula D8] to [ chemical formula D10] among the dopant compounds in the light emitting layer may be a compound represented by any one selected from the following [ D201] to [ D476 ].

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Further, in the present invention, the compound represented by any one of [ chemical formula D6] and [ chemical formula D7] among the dopant compounds in the light emitting layer may be a compound represented by any one selected from the following < D501> to < D587 >.

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At this time, the content of the dopant in the light emitting layer may be generally selected from the range of about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.

In addition, the light emitting layer may further include a plurality of host substances and a plurality of dopant substances in addition to the dopant and the host.

Further, as a preferred embodiment of the organic light-emitting element according to the present invention, the first light-emitting layer may contain one or more compounds selected from any one of the compounds represented by the [ chemical formula a ] and the [ chemical formula B ].

Here, in the case where the first light-emitting layer contains any one compound selected from the group consisting of compounds represented by [ chemical formula a ] and [ chemical formula B ] in the organic light-emitting element according to the present invention, an anthracene derivative represented by [ chemical formula E ] described below may be used as a host in the second light-emitting layer.

[ chemical formula E ]

In the above-mentioned [ formula E ],

the substituent R ₄₁ To R ₅₆ And are the same or different and are each independently selected from any one of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, a halogen group,

the substituent Ar ₅ Is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms,

the linker L ₁ Is any one selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms,

Wherein n is an integer of 1 to 2, and each linking group L in the case where n is 2 or more ₁ Are the same as or different from each other,

the "substituted" in the "substituted or unsubstituted" in the [ chemical formula E ] means a sulfur substituted with one of deuterium, cyano, halo, hydroxyl, nitro, alkyl having 1 to 24 carbon atoms, haloalkyl having 1 to 24 carbon atoms, alkenyl having 2 to 24 carbon atoms, alkynyl having 2 to 24 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, heteroalkyl having 1 to 24 carbon atoms, aryl having 6 to 24 carbon atoms, aralkyl having 7 to 24 carbon atoms, alkylaryl having 7 to 24 carbon atoms, heteroaryl having 2 to 24 carbon atoms, heteroaralkyl having 2 to 24 carbon atoms, alkoxy having 1 to 24 carbon atoms, alkylamino having 1 to 24 carbon atoms, diarylamino having 12 to 24 carbon atoms, diheteroarylamino having 2 to 24 carbon atoms, aryl (heteroaryl) amino having 7 to 24 carbon atoms, alkylsilyl having 1 to 24 carbon atoms, arylsilyl having 6 to 24 carbon atoms, aryl having 6 to 24 carbon atoms, and aryl having 6 to 24 carbon atoms.

In addition, the anthracene derivative represented by formula E in the second light emitting layer in the present invention may include at least one deuterium. In this case, the substituent R ₄₁ To R ₅₆ Ar, ar ₅ At least one substituent of (c) may be an aryl group having 6 to 18 carbon atoms substituted with deuterium.

Further, as a preferred embodiment of the organic light-emitting element according to the present invention, in the case where the second light-emitting layer contains an anthracene derivative represented by the [ chemical formula E ] as a main body, as a more preferred structure of the anthracene derivative represented by the [ chemical formula E ], an anthracene derivative represented by the following [ chemical formula E-1] or [ chemical formula E-2] may be used.

[ chemical formula E-1]

[ chemical formula E-2]

In the [ chemical formula E-1] and the [ chemical formula E-2],

the substituent R ₄₁ To R ₄₈ 、R ₄₉ To R ₅₅ Are each the same or different and are each independently selected from any one of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a cyano group, a nitro group, a halogen group,

the linker L ₁₁ Is any one selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms,

wherein k is an integer of 1 to 2, and in the case where k is 2 or more, each linking group L ₁₁ Are the same as or different from each other,

the "substituted" in the "substituted or unsubstituted" in the "chemical formula E-1" and the "chemical formula E-2" means an aryl group having 6 to 24 carbon atoms, an aralkyl group having 7 to 24 carbon atoms, an alkylaryl group having 7 to 24 carbon atoms, an alkoxy group having 2 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, a diarylamino group having 12 to 24 carbon atoms, a diheteroarylamino group having 2 to 24 carbon atoms, an aryl (hetero) group having 7 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms, a sulfur-substituted aryl group having 6 to 24 carbon atoms, an acyloxy group having 6 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms, an alkylsilyl group having 6 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 12 to 24 carbon atoms, a diarylamino group having 2 to 24 carbon atoms, an aryl group having 2 to 24 carbon atoms.

Further, as a more preferable example related to the "substituted" in the "substituted or unsubstituted" in the above-mentioned [ chemical formula E ], [ chemical formula E-1] and [ chemical formula E-2], it may be a member selected from the group consisting of deuterium, cyano, halo, hydroxy, nitro, alkyl having 1 to 12 carbon atoms, haloalkyl having 1 to 12 carbon atoms, alkenyl having 2 to 12 carbon atoms, alkynyl having 2 to 12 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, heteroalkyl having 1 to 12 carbon atoms, aryl having 6 to 18 carbon atoms, aralkyl having 7 to 20 carbon atoms, alkylaryl having 7 to 20 carbon atoms, heteroaryl having 2 to 18 carbon atoms, heteroarylalkyl having 2 to 18 carbon atoms, alkoxy having 1 to 12 carbon atoms, alkylamino having 1 to 12 carbon atoms, diarylamino having 12 to 18 carbon atoms, diarylamino having 2 to 18 carbon atoms, diarylamino having 7 to 18 carbon atoms, aryl having 7 to 18 carbon atoms, silyl having 6 to 18 carbon atoms, and an aryl group having 6 to 18 carbon atoms, and an oxygen group substituted by an aryl having 6 to 18 carbon atoms.

Here, by the [ formula E-1]]Or [ formula E-2]]The compound represented by the formula (I) is characterized in that, as shown in the following FIG. 1, the 1 or 2 position of the benzene ring on either side of dibenzofuran or the 1 'or 2' position of the benzene ring on the other side of dibenzofuran is bonded to an anthracene group or a linker L ₁₁ No. 9 position of (b).

Picture 1

In the present invention, the chemical reaction is carried out by the above-mentioned [ chemical reaction ]E (E)][ formula E-1]][ formula E-2]]Substituent Ar in anthracene derivative represented by any one of them ₅ May be represented by the following [ structural formula C-1]]A substituent represented by the formula (I).

[ Structure C-1]

At this time, the [ structural formula C-1]]R in ₆₁ To R ₆₅ Are each the same or different and are each independently selected from any one of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a halogen group,

the "-" in the [ structural formula C-1] is a binding site bound to the 10-position of the anthracene group in the [ chemical formula E ], [ chemical formula E-1] or [ chemical formula E-2 ].

As an embodiment, as a preferable example of the organic light emitting element according to the present invention, the [ chemical formula E-1 ]]Or [ formula E-2 ]]Inner linker L ₁₁ May be a single bond or a substituted or unsubstituted arylene group having 6 to 14 carbon atoms, wherein k is an integer of 1 to 2, and each L is 2 or more ₁₃ The same as or different from each other.

Further, as an embodiment according to the present invention, in the chemical formula E, ar ₅ May be a substituent comprising at least one deuterium, preferably Ar ₅ May be an aryl group having 6 to 50 carbon atoms containing at least one deuterium, more preferably Ar ₅ May be an aryl group having 6 to 40 carbon atoms containing deuterium, more preferably Ar ₅ May be an aryl group having 6 to 30 carbon atoms containing deuterium, more preferably Ar ₅ May be an aryl group having 6 to 24 carbon atoms containing deuterium, more preferablySelected as Ar ₅ May be an aryl group having 6 to 18 carbon atoms containing deuterium, more preferably Ar ₅ May be a phenyl group substituted with deuterium.

Furthermore, as an embodiment according to the present invention, in the chemical formula E, R ₄₁ To R ₄₈ At least one of them may be deuterium, preferably at least two may be deuterium, more preferably at least four may be deuterium, more preferably eight may be all deuterium.

Furthermore, as an embodiment according to the present invention, in the chemical formula E, R ₄₉ To R ₅₆ At least one of (a) may be a substituent containing deuterium, preferably may be an aryl group having 6 to 50 carbon atoms containing deuterium, more preferably may be an aryl group having 6 to 40 carbon atoms containing deuterium, more preferably may be an aryl group having 6 to 30 carbon atoms containing deuterium, more preferably may be an aryl group having 6 to 24 carbon atoms containing deuterium, more preferably may be an aryl group having 6 to 18 carbon atoms containing deuterium, more preferably in the chemical formula E, R ₄₉ To R ₅₆ One or both of them may be an aryl group having 6 to 18 carbon atoms substituted with deuterium.

In addition, as an embodiment of the present invention, the degree of deuteration of the anthracene derivative represented by the chemical formula E may be 20% or more, preferably 30% or more, more preferably 35% or more, more preferably 40% or more, more preferably 45% or more, more preferably 50% or more.

In addition, the term "deuterated derivative" of the compound X as used herein generally means that the compound X has the same structure as the compound X, but is accompanied by at least one deuterium (D) that replaces a hydrogen atom (H) bonded to a carbon atom, a nitrogen atom, an oxygen atom, or the like in the compound X.

At this time, the term "yy% deuterated" or "yy% deuterated" means that the ratio of deuterium to the sum of all hydrogen and deuterium directly bonded to a carbon atom, nitrogen atom, oxygen atom or the like in the compound X is expressed in percent.

Thus, if two of the six hydrogens of benzene are deuterated, then this can be considered compound C ₆ H ₄ D ₂ Is 2/(4+2) ×100=33% deuterated.

In the case where the anthracene derivative compound in the present invention is substituted with deuterium, the degree of deuteration thereof refers to the case where the ratio of all deuterium directly bonded to a carbon atom in the anthracene derivative to the sum of all hydrogen directly bonded to a carbon atom in the anthracene derivative is expressed as a percentage.

For example, in the case of an anthracene derivative represented by the following compound Z, since there are 5 deuterium in a phenyl group bonded to an anthracene group and 5 deuterium in a phenyl group bonded to a dibenzofuran group, there are 10 total deuterium, 8 hydrogen atoms are bonded to the anthracene group, 6 hydrogen atoms are bonded to aromatic carbon atoms in six-membered rings on both sides of the dibenzofuran group, and thus the deuteration degree thereof can be represented as 100×10/(10+8+6) =41.7%.

[ Compound Z ]

In addition, in the case of a specific substituent, the degree of deuteration may be different depending on each individual substituent, and therefore, the degree of deuteration may be represented by determining the degree of substitution on average.

As an example, it is observed that a part of the anthracene group substituted with deuterium, although it is also possible to prepare an anthracene derivative having deuterium bonded to all carbon atoms according to the reaction conditions to use it as the anthracene group substituted with deuterium, it is possible to obtain a product in which a compound having hydrogen bonded to carbon atom(s) of a specific position or a specific moiety (mole) and a compound having deuterium bonded thereto exist in a mixture form according to the reaction conditions, and it may be very difficult to separate them, in which case the degree of substitution with deuterium can be calculated from the overall structural formula by finding the degree of substitution with deuterium on average and referring thereto.

In the present invention, as described above, the anthracene derivative substituted with deuterium is also used in the anthracene derivative represented by the [ chemical formula E ], whereby the lifetime of the organic light-emitting element can be further improved.

The anthracene derivative represented by the [ chemical formula E ] in the organic light-emitting element according to the present invention may be any one selected from the following < compound 201> to < compound 506 >.

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Hereinafter, an organic light emitting element according to an embodiment of the present invention is described with reference to the accompanying drawings.

Fig. 1 is a diagram showing a structure of an organic light emitting element according to an embodiment of the present invention.

As shown in fig. 1, the organic light emitting device according to an embodiment of the present invention is an organic light emitting device including an anode 20, a hole transporting layer 40, first and second light emitting layers 50-a and 50-B including a host and a dopant, an electron transporting layer 60, and a cathode 80 in this order, which corresponds to an organic light emitting device including the anode as a first electrode, the cathode as a second electrode, a hole transporting layer between the anode and the light emitting layer, and an electron transporting layer between the light emitting layer and the cathode.

In addition, the organic light emitting element according to an embodiment of the present invention may include a hole injection layer 30 between the anode 20 and the hole transport layer 40, and an electron injection layer 70 between the electron transport layer 60 and the cathode 80.

The organic light emitting device and the method of manufacturing the same according to the present invention will be described below with reference to fig. 1.

First, a substance for a positive electrode (anode) is coated on the upper portion of the substrate 10 to form an anode 20. Among them, the substrate 10 is preferably an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, handleability and water repellency, although a substrate used in a general organic EL element is used. Further, indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin oxide (SnO) which is transparent and excellent in conductivity are used as the anode electrode material ₂ ) OxygenZinc oxide (ZnO), and the like.

A hole injection layer material is vacuum thermally deposited or spin-coated on the upper portion of the electrode of the anode 20 to form a hole injection layer 30. Then, a hole transport layer substance is vacuum thermally deposited or spin-coated on the upper portion of the hole injection layer 30 to form a hole transport layer 40.

The hole injection layer material may be any material commonly used in the art, and for example, 4',4″ -tris [ 2-naphthylphenyl-phenylamino ] triphenylamine (2-TNATA: 4,4',4″ -tris (2-workbench-phenyl) -triphenylamine), N ' -bis (1-naphthyl) -N, N ' -diphenylbenzidine (NPD: N, N ' -di (1-workbench) -N, N ' -diphenylbenzine), N ' -diphenyl-N, N ' -bis (3-methylphenyl) -1,1' -biphenyl-4,4' -diamine (TPD: N, N ' -diphenyl-N, N ' -bis (3-workbench) -1,1' -biphen-4, 4' -diene), N ' -diphenyl-N, N ' -diphenyl-4- [ phenyl ] -4- (4-phenyl) -4 ' -diamino ] -4, etc. may be used. However, the present invention is not necessarily limited thereto.

The material of the hole transport layer is not particularly limited as long as it is a material commonly used in the art, and for example, N ' -bis (3-methylphenyl) -N, N ' -diphenyl- [1, 1-biphenyl ] -4,4' -diamine (TPD), N ' -bis (naphthalen-1-yl) -N, N ' -diphenyl benzidine (a-NPD), or the like can be used. However, the present invention is not necessarily limited thereto.

In addition, the present invention may additionally form an electron blocking layer on top of the hole transport layer. The electron blocking layer is a layer for preventing electrons injected from the electron injection layer from entering the hole transport layer through the light emitting layer, thereby improving the lifetime and efficiency of the element, and may be formed at a suitable portion between the light emitting layer and the hole injection layer, preferably, may be formed between the light emitting layer and the hole transport layer.

Next, the first light emitting layer 50-a and the second light emitting layer 50-B may be sequentially stacked on top of the hole transport layer 40 or the electron blocking layer by a vacuum deposition method or a spin coating method.

Here, each of the first light emitting layer and the second light emitting layer may be composed of a host and a dopant, and the materials constituting them are the same as those described previously.

That is, the light emitting layers as the first and second light emitting layers 50-a and 50-B may be formed by separate deposition processes or coating processes, respectively, using host materials and dopant materials that are the same or different from each other.

More preferably, the first light emitting layer may include one or more compounds represented by the chemical formula a or chemical formula B as a fluorescent host, the second light emitting layer may include one or more anthracene derivatives represented by the chemical formula E, and as fluorescent dopants in each of the first and second light emitting layers, one or more materials selected from the chemical formulas D1 to D10 may be used as materials that are the same or different independently from each other.

Further, as a host material usable in the first light-emitting layer and the second light-emitting layer in the present invention, a host material (BH 1) used for the first light-emitting layer is preferably a material having a lower lowest unoccupied molecular orbital function (LUMO) and a higher highest occupied molecular orbital function (HOMO) than a host material (BH 2) used for the second light-emitting layer, and thus has a structure in which holes (Hole) and/or electrons (Electron) are easily injected than a host (BH 2) used for the second light-emitting layer.

And, according to a specific example of the present invention, the thickness of each light emitting layer is preferablyTo->

Further, in the case where the sum of the thicknesses of the first light-emitting layer and the second light-emitting layer is set to 100, the thickness of the first light-emitting layer (including the compound represented by chemical formula a or chemical formula B) and the second light-emitting layer (including the anthracene derivative represented by chemical formula E) in the present invention is preferably 10% to 70%, more preferably, may be in the range of 20% to 50%.

In addition, an electron transport layer 60 is deposited on the light emitting layer by a vacuum deposition method or a spin coating method.

In the present invention, the material of the electron transport layer is a material that functions to stably transport electrons injected from an electron injection electrode (Cathode), and a known electron transport substance can be used. As examples of the known electron-transporting substances, quinoline derivatives, in particular tris (8-hydroxyquinoline) aluminum (Alq ₃ ) Materials such as Liq, TAZ, BAlq, bis (benzoquinoline-10-hydroxy) beryllium (berylium bis (benzoquinoline-10-olate: bebq 2), E201, E202, BCP, PBD, BMD, BND as an oxadiazole derivative, etc., but are not limited thereto.

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Further, the organic light emitting element in the present invention may be stacked on top of the electron transport layer after the electron transport layer is formed as an Electron Injection Layer (EIL) having a function of enabling easy injection of electrons from the cathode, and the material thereof is not particularly limited.

As the electron injection layer forming material, for example, csF, naF, liF, li can be used ₂ O, baO, etc. are known as electron injection layer forming materials. Although the deposition conditions of the electron injection layer are different depending on the compound used, it is generally possible to select from a range of conditions substantially identical to those of the formation of the hole injection layer.

The electron injection layer may have a thickness of aboutTo about->Preferably about->To about->If the thickness of the electron injection layer satisfies the aforementioned range, a satisfactory degree of electron injection characteristics can be obtained without a substantial increase in the driving voltage.

Also, the cathode in the present invention may use a substance having a small work function to easily inject electrons. Aluminum (Al), aluminum-lithium (Al-Li), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or the like, such as lithium (Li), magnesium (Mg), calcium (Ca), or their alloys, may be used, or a transmissive cathode using ITO, IZO may be employed.

Also, in the present invention, the organic light emitting element may additionally include a light emitting layer of a blue light emitting material, a green light emitting material, or a red light emitting material that emits light in a wavelength range of 380nm to 800 nm. That is, the light emitting layer in the present invention is a plurality of light emitting layers, and the blue light emitting material, the green light emitting material, or the red light emitting material in the additionally formed light emitting layer may be a fluorescent material or a phosphorescent material.

Also, in the present invention, one or more layers selected from the respective layers may be formed by a single molecule deposition process or a solution process.

Wherein the deposition process means a method of forming a thin film by evaporating a substance used as a material for forming the respective layers by heating or the like in a vacuum or low pressure state, and the solution process means a method of mixing a substance used as a material for forming the respective layers with a solvent and forming a thin film by a method such as ink-jet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating, or the like.

The organic light-emitting element according to the present invention can be used in any one device selected from a flat panel display device, a flexible display device, a device for single-color or white flat panel illumination, and a device for single-color or white flexible illumination.

Hereinafter, the present invention will be described in more detail by way of preferred examples. However, these examples are merely for more specifically explaining the present invention, and those having a basic knowledge in the art can clearly understand that the scope of the present invention is not limited thereto.

Example (example)

< preparation of host Compound >

Synthesis example 1 Synthesis of chemical formula 19

Synthesis example 1-1.<1-a>Is synthesized by (a)

[ reaction type 1]

A3000 ml round bottom flask was purged with nitrogen and charged with 100g (0.278 mol) of 1, 6-dibromopyrene, 33.9g (0.278 mol) of phenylboronic acid, tetrakis (triphenylphosphine) palladium (Pd [ PPh) ₃ ] ₄ ) 6.4g (0.006 mol), 88.3g (0.833 mol) of sodium carbonate, 1400ml of toluene and 420ml of water and refluxed for 9 hours. When the reaction was completed, after cooling to room temperature, the resultant solid was filtered and discarded, and after extracting the filtrate with ethyl acetate and water, the organic layer was subjected to anhydrous treatment. Concentrating the organic layer under reduced pressure after anhydrous treatment, and separating by column chromatography<1-a>45.4g (yield 45.7%).

Synthesis example 1-2 Synthesis of <1-b >

[ reaction type 2]

A500 ml round bottom flask was purged with nitrogen and charged with 20g (0.076 mol) of 6-bromo-1-dibenzofuranol, 11.6g (0.091 mol) of phenylboronic acid (D5), and tetrakis (triphenylphosphine) palladium(Pd[PPh ₃ ] ₄ ) 1.8g (0.002 mol), 17.9g (0.129 mol) of potassium carbonate, 140ml of toluene, 35ml of ethanol and 65ml of water were refluxed for 5 hours. When the reaction was completed, after cooling to room temperature, extraction was performed with ethyl acetate and water, and the organic layer was subjected to anhydrous treatment. The organic layer was concentrated under reduced pressure and recrystallized from ethyl acetate and heptane to give <1-b>15.2g (yield 75.4%).

Synthesis examples 1 to 3.<1-c>Is synthesized by (a)

[ reaction type 3]

A500 ml round bottom flask was purged with nitrogen and charged with <1-b >15.2g (0.058 mol) and pyridine 6g (0.076 mol) and 150ml of dichloromethane and the temperature was cooled to below 0deg.C. After cooling, 18.1g (0.064 mol) of trifluoromethanesulfonic anhydride (Trifluoromethanesulfonic anhydride) was slowly added dropwise. After the dropwise addition, the reaction mixture was warmed to room temperature and stirred until the reaction was completed. When the reaction was completed, extraction was performed with methylene chloride and water, then, the organic layer was subjected to anhydrous treatment, then, distillation under reduced pressure was performed, and separation was performed by column chromatography to obtain <1-c >20g (yield 87.3%).

Synthesis examples 1 to 4.<1-d>Is synthesized by (a)

[ reaction type 4]

To a 300ml round bottom flask was purged with nitrogen, <1-c >20g (0.050 mol), bis (pinacolato) diboron (Bis (pinacolato) diboron) 16.6g (0.065 mol), bis diphenylphosphino ferrocene palladium dichloride (1, 1' -Bis (diphenylphosphino) ferrocene ] dichlorpaladi) 0.8g (0.001 mol), calcium acetate 9.9g (0.101 mol) and 1, 4-dioxane 200ml were placed and refluxed for 12 hours. When the reaction was completed, the reaction mixture was cooled to room temperature, then, it was filtered through celite, and the filtrate was concentrated and separated by column chromatography to give <1-d >14.8g (yield 78.4%).

Synthesis examples 1 to 5 [ chemical formula 19]]Is synthesized by (a)

[ reaction type 5]

To a 300ml round bottom flask was purged with nitrogen, placed <1-a >10.7g (0.030 mol), <1-d >13.7g (0.036 mol), 0.7g (0.001 mol) of tetrakis (triphenylphosphine) palladium, 7.4g (0.053 mol) of potassium carbonate, 80ml of toluene, 20ml of ethanol, and 26ml of water, and refluxed for 4 hours. When the reaction was completed, the mixture was cooled to room temperature, and extracted with ethyl acetate and water. The organic layer was concentrated after anhydrous treatment, and separated by column chromatography to obtain 8.4g (yield 53.4%) of [ chemical formula 19 ].

MS(MALDI-TOF)：m/z 525.21[M] ⁺

Synthesis example 2 Synthesis of formula 34

Synthesis example 2-1.<2-a>Is synthesized by (a)

[ reaction type 6]

/>

Synthesis example 1-1 was repeated in the same manner with the exception of using phenylboronic acid (D5) in place of phenylboronic acid used in Synthesis example 1-1 to obtain <2-a > (yield 79.3%).

Synthesis example 2-2.<2-b>Is synthesized by (a)

[ reaction type 7]

The synthesis was performed in the same manner as in Synthesis example 1-2 except that 1, 7-dibromodibenzofuran was used in place of 6-bromo-1-dibenzofuranol used in Synthesis example 1-2, to obtain <2-b > (yield 54%).

Synthesis examples 2 to 3.<2-c>Is synthesized by (a)

[ reaction type 8]

Synthesis was conducted in the same manner as in Synthesis examples 1 to 4 except that <2-b > was used in place of <1-c > used in Synthesis examples 1 to 4, to obtain <2-c > (yield 72.8%).

Synthesis examples 2 to 4 [ chemical formula 34]]Is synthesized by (a)

[ reaction type 9]

[ chemical formula 34] (yield 63.7%) was obtained by synthesizing in the same manner as in Synthesis example 1-5 except that <2-a > was used in place of <1-a > used in Synthesis example 1-5 and <2-c > was used in place of <1-d >.

MS(MALDI-TOF)：m/z 530.25[M] ⁺

Synthesis example 3 Synthesis of chemical formula 52

Synthesis example 3-1.<3-a>Is synthesized by (a)

[ reaction type 10]

The synthesis was performed in the same manner as in Synthesis example 1-2 except that 6-bromo-2-dibenzofuran alcohol was used instead of 6-bromo-1-dibenzofuran alcohol used in Synthesis example 1-2 and phenylboronic acid (D5) was used instead of phenylboronic acid, to obtain <3-a > (yield 72.0%).

Synthesis example 3-2.<3-b>Is synthesized by (a)

[ reaction type 11]

Synthesis example 1-3 was repeated in the same manner as in Synthesis example 1-3 except that <3-a > was used in place of <1-b > used in Synthesis example 1-3 to obtain <3-b > (yield 85.2%).

Synthesis examples 3 to 3.<3-c>Is synthesized by (a)

[ reaction type 12]

Synthesis was performed in the same manner as in Synthesis examples 1 to 4 except that <3-b > was used in place of <1-c > used in Synthesis examples 1 to 4, to obtain <3-c > (yield 76.8%).

Synthesis examples 3 to 4 [ chemical formula 52]]Is synthesized by (a)

[ reaction type 13]

[ chemical formula 52] (yield 58.0%) was obtained by synthesizing in the same manner as in Synthesis examples 2-4 except that <3-c > was used instead of <2-c > in Synthesis examples 2-4.

MS(MALDI-TOF)：m/z 525.21[M] ⁺

Synthesis example 4 Synthesis of chemical formula 131

Synthesis example 4-1 [ chemical formula 131]]Is synthesized by (a)

[ reaction type 14]

[ chemical formula 131] (yield 61.4%) was obtained by synthesizing in the same manner as in Synthesis examples 2-4, except that 1-dibenzofuran boric acid was used instead of <2-c > used in Synthesis examples 2-4.

MS(MALDI-TOF)：m/z 449.18[M] ⁺

Synthesis example 5 Synthesis of chemical formula 136

Synthesis example 5-1.<5-a>Is synthesized by (a)

[ reaction type 15]

To a 1000ml round bottom flask was purged with nitrogen, 50ml (0.477 mol) of 30wt% aqueous hydrogen peroxide, 45g (0.454 mol) of phenol (D5), 57.6g (0.227 mol) of iodine and 450ml of water were placed and stirred at 50℃for 24 hours. When the reaction was completed, an aqueous sodium thiosulfate solution was added thereto and stirred, and the reaction solution was extracted with ethyl acetate and water, and then subjected to anhydrous treatment and concentrated under reduced pressure. After concentration, the mixture was separated by column chromatography to give <5-a >45g (yield: 44.3%).

Synthesis example 5-2 Synthesis of <5-b >

[ reaction type 16]

To a 1000ml round bottom flask was purged nitrogen, placed <5-a >45g (0.201 mol), 41g (0.241 mol) of 2-fluoro-6-methoxyphenylboronic acid, 7g (0.006 mol) of tetrakis (triphenylphosphine) palladium, 47.2g (0.341 mol) of potassium carbonate, 315ml of toluene, 80ml of ethanol and 170ml of water, and refluxed for 8 hours. When the reaction was completed, after cooling to room temperature, extraction was performed with ethyl acetate and water, and then the organic layer was subjected to anhydrous treatment. The organic layer was concentrated under reduced pressure and separated by column chromatography to give <5-b >28.6g (yield 64.1%).

Synthesis examples 5 to 3.<5-c>Is synthesized by (a)

[ reaction type 17]

To a 500ml round bottom flask was added <5-b >28.6g (0.129 mol), potassium carbonate 44.5g (0.322 mol), 1-methyl-2-pyrrolidine 143ml and refluxed for 12 hours. When the reaction was completed, the temperature was cooled to room temperature, 200ml of a 2N-hydrochloric acid aqueous solution was slowly added thereto with stirring, followed by extraction with ethyl acetate and water. The organic layer was concentrated and separated by column chromatography to give <5-c >21g (yield 80.7%).

Synthesis examples 5 to 4.<5-d>Is synthesized by (a)

[ reaction type 18]

To a 500ml round bottom flask was added <5-c >21g (0.104 mol), dichloromethane 120ml and the reaction was cooled to below 0 ℃. The temperature was noted and 52g (0.208 mol) of boron tribromide was slowly added dropwise. After the dropwise addition, the reaction mixture was warmed to room temperature and stirred until the reaction was completed. When the reaction was completed, 100ml of water was slowly added dropwise to the reaction solution, followed by stirring thoroughly. After the reaction solution was extracted with methylene chloride and water, the reaction solution was subjected to anhydrous treatment and concentration under reduced pressure, and then separated by column chromatography to obtain <5-d >15g (yield 76.8%).

Synthesis examples 5 to 5.<5-e>Is synthesized by (a)

[ reaction type 19]

Nitrogen was purged into a 500ml round bottom flask, and <5-d >15.0g (0.080 mol), 8.2g (0.104 mol) of pyridine, and 150ml of methylene chloride were placed, and the reaction mixture was cooled to a temperature of 0℃or lower. After cooling, 24.7g (0.088 mol) of trifluoromethanesulfonic anhydride (Trifluoromethanesulfonic anhydride) was slowly added dropwise. After the dropwise addition, the reaction solution was warmed to room temperature and stirred until the reaction was completed. When the reaction was completed, extraction was performed with methylene chloride and water, then the organic layer was subjected to anhydrous treatment and concentrated under reduced pressure, and then separated by column chromatography to obtain <5-e >20g (yield 78.4%).

Synthesis examples 5 to 6.<5-f>Is synthesized by (a)

[ reaction type 20]

To a 500ml round bottom flask was purged nitrogen and placed <5-e >20g (0.062 mol), bis (pinacolato) diboron 23.8g (0.094 mol), bis-diphenylphosphino ferrocene palladium dichloride 2.5g (0.003 mol), calcium acetate 9.5g (0.125 mol) and 1, 4-dioxane 200ml and refluxed for 12 hours. When the reaction was completed, the reaction mixture was cooled to room temperature, then, it was filtered through celite, and the filtrate was concentrated and separated by column chromatography to give <5-f >15g (yield 80.6%).

Synthesis examples 5 to 7 [ chemical formula 136]]Is synthesized by (a)

[ reaction type 21]

[ chemical formula 136] (yield 60.3%) was obtained by synthesizing in the same manner as in Synthesis examples 2-4 except that <5-f > was used instead of <2-c > in Synthesis examples 2-4.

MS(MALDI-TOF)：m/z 453.21[M] ⁺

Synthesis example 6 Synthesis of chemical formula 41

Synthesis example 6-1 [ chemical formula 41]]Is synthesized by (a)

[ reaction type 22]

[ chemical formula 41] (yield 54.2%) was obtained by synthesizing in the same manner as in Synthesis examples 1 to 5 except that <2-a > was used instead of <1-a > used in Synthesis examples 1 to 5.

MS(MALDI-TOF)：m/z 530.25[M] ⁺

Synthesis example 7 Synthesis of formula 57

Synthesis example 7-1 [ chemical formula 57]]Is synthesized by (a)

[ reaction type 23]

[ chemical formula 57] (yield 53.5%) was obtained by synthesizing in the same manner as in Synthesis examples 1-5 except that <3-c > was used instead of <1-d > used in Synthesis examples 1-5.

MS(MALDI-TOF)：m/z 520.18[M] ⁺

< preparation of dopant Compound >

Synthesis example 8 Synthesis of D202

Synthesis example 8-1.<8-a>Is synthesized by (a)

[ reaction type 24]

To a 100mL reactor were placed 3.1g (16 mmol) of 1-bromo-3-chlorobenzene, 5.8g (16 mmol) of aniline, 0.1g (1 mmol) of palladium acetate, 3g (32 mmol) of sodium t-butoxide, 0.2g (1 mmol) of bis (diphenylphosphino) -1,1' -binaphthyl, 45mL of toluene and stirred under reflux for 24 hours. After the reaction was completed, the filtrate was filtered and concentrated, and separated by column chromatography to give <8-a >5.2g. (yield 82%)

Synthesis example 8-2.<8-b>Is synthesized by (a)

[ reaction type 25]

To a 250mL reactor were placed <8-a >20g (98 mmol), 3-bromobenzothiophene 20.9g (98 mmol), palladium acetate 0.5g (2 mmol), sodium t-butoxide 18.9g (196 mmol), tri-t-butylphosphine 0.8g (4 mmol), toluene 200mL, and stirred under reflux for 5 hours. After the reaction was completed, the filtrate was filtered and concentrated, and separated by column chromatography to give <8-b >24.7g. (yield 75%)

Synthesis example 8-3.<8-c>Is synthesized by (a)

[ reaction type 26]

To a 100mL reactor were placed <8-b >5.4g (16 mmol), aniline 5.8g (16 mmol), palladium acetate 0.1g (1 mmol), sodium t-butoxide 3g (32 mmol), bis (diphenylphosphino) -1,1' -binaphthyl 0.2g (1 mmol), toluene 45mL, and stirred under reflux for 24 hours. After the reaction was completed, the filtrate was filtered and concentrated, and separated by column chromatography to give <8-c >4.6g. (yield 73%)

Synthesis examples 8 to 4.<8-d>Is synthesized by (a)

[ reaction type 27]

A reaction was conducted in the same manner as in Synthesis example 8-2 except that <8-c > was used in place of <8-a > used in Synthesis example 8-2 and 1-bromo-2-iodobenzene was used in place of 3-bromobenzothiophene, whereby <8-d > was obtained. (yield 77%)

Synthesis examples 8 to 5.<D202>Is synthesized by (a)

[ reaction type 28]

To a 300mL reactor was placed <8-d >12.6g (23 mmol), tert-butylbenzene 120mL. 42.5mL (68 mmol) of n-butyllithium was added dropwise at-78deg.C. After the dropwise addition, the mixture was stirred at 60℃for 3 hours. Then, nitrogen was purged at 60 ℃ to remove heptane. 11.3g (45 mmol) of boron tribromide are added dropwise at-78 ℃. After the dropwise addition, the mixture was stirred at room temperature for 1 hour, and 5.9g (45 mmol) of N, N-diisopropylethylamine was added dropwise at 0 ℃. After the dropwise addition, the mixture was stirred at 120℃for 2 hours. After the reaction, an aqueous sodium acetate solution was added thereto at room temperature and stirred. Extraction with ethyl acetate and concentration of the organic layer, separation by column chromatography gave < D202>1.1g. (yield 10%)

MS(MALDI-TOF)：m/z 476.15[M ⁺ ]

Synthesis example 9 Synthesis of D265

Synthesis example 9-1.<9-a>Is synthesized by (a)

[ reaction type 29]

Synthesis example 8-1 was repeated in the same manner with the exception of using 1-bromo-2, 3-dichlorobenzene in place of 1-bromo-3-chlorobenzene in Synthesis example 8-1 to obtain <9-a >. (yield 71%)

Synthesis example 9-2.<9-b>Is synthesized by (a)

[ reaction type 30]

/>

The synthesis was performed in the same manner as in Synthesis example 8-2 except that diphenylamine was used in place of <8-a > used in Synthesis example 8-2 and 1-bromo-3-iodobenzene was used in place of 1-bromo-3-chlorobenzene, thereby obtaining <9-b >. (yield 77%)

Synthesis example 9-3.<9-c>Is synthesized by (a)

[ reaction type 31]

A reaction was conducted in the same manner as in Synthesis example 8-2 except that <9-a > was used in place of <8-a > used in Synthesis example 8-2 and <9-b > was used in place of 1-bromo-3-chlorobenzene, whereby <9-c > was obtained. (yield 75%)

Synthesis examples 9 to 4.<9-d>Is synthesized by (a)

[ reaction type 32]

To a 1L reactor were placed 30g (174 mmol) of 3-bromoaniline, 25.5g (209 mmol) of phenylboronic acid, 4g (3 mmol) of tetrakis (triphenylphosphine) palladium, 48.2g (349 mmol) of potassium carbonate, 150mL of 1, 4-dioxane, 150mL of toluene, 90mL of distilled water and stirred under reflux for 4 hours. After the completion of the reaction, the organic layer was concentrated under reduced pressure by separating the organic layer by column chromatography to give <9-d >24g. (yield 80%)

Synthesis examples 9 to 5.<9-e>Is synthesized by (a)

[ reaction type 33]

Synthesis was conducted in the same manner as in Synthesis example 8-1 except that 3-bromobenzofuran was used instead of 1-bromo-3-chlorobenzene in Synthesis example 8-1 and <9-d > was used instead of aniline, whereby <9-e > was obtained. (yield 68%)

Synthesis examples 9 to 6.<9-f>Is synthesized by (a)

[ reaction type 34]

A reaction was conducted in the same manner as in Synthesis example 8-2 except that <9-c > was used in place of <8-a > used in Synthesis example 8-2 and <9-e > was used in place of 1-bromo-3-chlorobenzene, whereby <9-f > was obtained. (yield 68%)

Synthesis examples 9 to 7.<D265>Is synthesized by (a)

[ reaction type 35]

To a 250mL reactor was placed <9-f >21g (37 mmol), t-butylbenzene. 42.4mL (74 mmol) of t-butyllithium was added dropwise at-78deg.C. After the dropwise addition, the mixture was stirred at 60℃for 3 hours. Then, nitrogen was blown at 60℃to remove pentane. 7.1mL (74 mmol) of boron tribromide was added dropwise at-78 ℃. After the dropwise addition, the mixture was stirred at room temperature for 1 hour, and 6g (74 mmol) of N, N-diisopropylethylamine was added dropwise at 0 ℃. After the dropwise addition, the mixture was stirred at 120℃for 2 hours. After the reaction was completed, an aqueous sodium acetate solution was added thereto at room temperature and stirred. The organic layer was extracted with ethyl acetate and concentrated and separated by column chromatography to give < D265>2.0g. (yield 17%)

MS(MALDI-TOF)：m/z 703.28[M ⁺ ]

Synthesis example 10 Synthesis of formula D459

Synthesis example 10-1.<10-a>Is synthesized by (a)

[ reaction type 36]

A <10-a > was synthesized in the same manner as in Synthesis example 8-2, except that 4a,9 a-dimethyl-2, 3, 4a,9 a-hexahydro-1H-carbazole was used in place of <8-a > used in Synthesis example 8-2 and 1-bromo-2, 3-dichloro-5-methylbenzene was used in place of 3-bromobenzothiophene. (yield 32%)

Synthesis example 10-2.<10-b>Is synthesized by (a)

[ reaction type 37]

Synthesis was conducted in the same manner as in Synthesis example 8-1 except that 3- (1-naphthyl) -1-bromobenzene was used instead of 1-bromo-3-chlorobenzene in Synthesis example 8-1, to obtain <10-b >. (yield 77%)

Synthesis example 10-3.<10-c>Is synthesized by (a)

[ reaction type 38]

A reaction was conducted in the same manner as in Synthesis example 8-2 except that <10-b > was used in place of <8-a > used in Synthesis example 8-2 and 1-bromo-3-iodobenzene was used in place of 3-bromobenzothiophene, whereby <10-c > was obtained. (yield 64%)

Synthesis example 10-4.<10-d>Is synthesized by (a)

[ reaction type 39]

Synthesis example 8-1 was repeated in the same manner with the exception of using <10-c > in place of 1-bromo-3-chlorobenzene in Synthesis example 8-1 to obtain <10-d >. (yield 75%)

Synthesis examples 10 to 5.<10-e>Is synthesized by (a)

[ reaction type 40]

A <10-e > was synthesized in the same manner as in Synthesis example 8-2, except that <10-d > was used in place of <8-a > used in Synthesis example 8-2 and <10-a > was used in place of 3-bromobenzothiophene. (yield 65%)

Synthesis examples 10 to 6.<D459>Is synthesized by (a)

[ reaction type 41]

A < D459> was synthesized in the same manner as in Synthesis example 9-7, except that <10-e > was used in place of <9-f > used in Synthesis example 9-7. (yield 11%)

MS(MALDI-TOF)：m/z 759.38[M ⁺ ]

Examples 1 to 46: manufacture of organic light emitting element comprising first and second light emitting layers

The light-emitting area of the ITO glass was set to a size of 2mm×2mm by patterning, and then the ITO glass was cleaned. After the ITO glass is arranged in the vacuum cavity, the basic pressure reaches 1 multiplied by 10 ^-7 Support and then DNTPDα-NPDIs formed over the ITO in this order. The light-emitting layer was sequentially formed into a first light-emitting layer and a second light-emitting layer, and in the first light-emitting layer, a film was formed by mixing a pyrene compound (a compound represented by chemical formula a or chemical formula B) according to the present invention with a BD dopant compound (1 wt%) described below>The second light-emitting layer is formed by mixing an anthracene compound (a compound represented by a chemical formula E) according to the present invention with a BD dopant compound (1 wt%) described below>Thereafter, [ E-1 ]]And [ E-2 ]]In a ratio of 1:1->Film formation as electron transport layer according to [ E-2 ]]/>AlAn organic light-emitting element is manufactured as an electron injection layer by sequential film formation of (a). The light emission characteristics of the organic light emitting element were measured at 0.4 mA.

TABLE 1

/>

Comparative examples 1 to 18

The organic light-emitting elements used in comparative examples 1 to 18 were produced in the same manner except that the compounds used in the first light-emitting layer and the second light-emitting layer of examples 1 to 46 were used and the compounds described in the following table were used, and the light-emitting characteristics of the organic light-emitting elements were measured at 0.4 mA.

TABLE 2

/>

As shown in tables 1 and 2, the organic light-emitting element according to the present invention is excellent in light-emitting efficiency and exhibits characteristics of low-voltage driving and long life, compared with the organic light-emitting element using the compound according to the comparative example of the related art, and thus it is known that the organic light-emitting element has high application possibility.

Industrial applicability

The organic light emitting element using the compound according to the present invention for manufacturing a light emitting layer has improved high efficiency, low voltage driving and long life characteristics compared to the conventional compound, and exhibits improved characteristics when applied to an organic light emitting element, so that the organic light emitting element and the related industrial fields have high industrial applicability.

Claims

1. An organic light-emitting element, characterized by comprising:

a first electrode; and

a second electrode facing the first electrode,

the first electrode and the second electrode sequentially comprise:

a first light emitting layer comprising a first host and a first dopant; and

a second light emitting layer comprising a second host and a second dopant,

wherein at least one of the first and second bodies comprises one or more compounds represented by the following [ formula a ] or [ formula B ]:

In the [ chemical formula A ] and the [ chemical formula B ],

2. The organic light-emitting device according to claim 1, wherein,

the compound represented by the formula a contains at least one deuterium,

the compound represented by the chemical formula B contains at least one deuterium.

3. The organic light-emitting device according to claim 2, wherein,

said [ formula A ]]R in (a) ₁ To R ₇ At least one of which is a substituent comprising deuterium,

said [ formula B ]]R in (a) ₈ To R ₁₄ At least one of which is a substituent comprising deuterium.

4. The organic light-emitting device according to claim 2, wherein,

at least one R in the [ formula A ] is a substituent containing deuterium,

at least one R' in the [ formula B ] is a substituent comprising deuterium.

5. The organic light-emitting device according to claim 1, wherein,

said [ formula A ]]R in (a) ₁ To R ₇ At least one of which is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms,

said [ formula B ]]R in (a) ₈ To R ₁₄ At least one of which is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.

6. The organic light-emitting device according to claim 1, wherein,

the linker L in the chemical formula A and the chemical formula B ₁ And L ₂ Is a single bond, or is selected from the following [ formula 1]]To [ Structure 5 ]]Any one of the following:

the carbon position of the aromatic ring in the linker may be bonded with hydrogen or deuterium.

7. The organic light-emitting device according to claim 6, wherein,

the linker L ₁ And L ₂ Respectively single bond。

8. The organic light-emitting device according to claim 1, wherein,

at least one R in the [ formula A ] is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms,

at least one R' in the [ formula B ] is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.

9. The organic light-emitting device according to claim 8, wherein,

the n3 and n4 in the chemical formula a and chemical formula B are each 1,

r in the [ chemical formula A ] is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms,

r' in the [ chemical formula B ] is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.

10. The organic light-emitting device according to claim 1, wherein,

the organic compound represented by the [ chemical formula A ] or [ chemical formula B ] is a compound represented by any one of the following [ chemical formula A-1] or [ chemical formula B-1 ]:

In the [ chemical formula A-1] and the [ chemical formula B-1],

the substituent R ₁ To R ₁₄ Linker L ₁ And L ₂ N1 and n2 and [ formula A ] in claim 1]Or [ formula B ]]The content defined in (a) is the same,

11. The organic light-emitting device according to claim 1, wherein,

the n3 and n4 in the chemical formula a and chemical formula B are each 1,

said [ formula A ]]R in (a) ₁ To R ₇ At least one of R is an aryl group having 6 to 18 carbon atoms substituted with deuterium,

said [ formula B ]]R in (a) ₈ To R ₁₄ At least one of R' is an aryl group having 6 to 18 carbon atoms substituted with deuterium.

12. The organic light-emitting device according to claim 1, wherein,

the n3 and n4 in the chemical formula a and chemical formula B are each 1,

r in the [ chemical formula A ] is a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms,

r' in the [ chemical formula B ] is a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms.

13. The organic light-emitting device according to claim 1, wherein,

the compound is any one selected from the group represented by the following chemical formulas 1 to 240:

/>

14. The organic light-emitting device according to claim 1, wherein,

at least one of a hole transport layer and a hole injection layer is provided between the first electrode and the first light-emitting layer,

at least one of an electron transport layer and an electron injection layer is provided between the second light-emitting layer and the second electrode.

15. The organic light-emitting device according to claim 1, wherein,

at least one of the first dopant in the first light emitting layer or the second dopant in the second light emitting layer uses a compound selected from any one or more of the following [ chemical formula D1] to [ chemical formula D10 ]:

[ chemical formula D1]

[ chemical formula D2]

the W and W' are selected from N-R ₅₃ 、CR ₅₄ R ₅₅ 、SiR ₅₆ R ₅₇ 、GeR ₅₈ R ₅₉ Either one of O, S, se;

the substituent R ₅₁ To R ₅₉ 、Ar ₂₁ To Ar ₂₈ Are each the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, and a substituted or unsubstituted alkenyl group A substituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylgermanium group having 1 to 30 carbon atoms, a substituted or unsubstituted arylgermanium group having 1 to 30 carbon atoms, a cyano group, a nitro group, a halogen group,

the R is ₅₁ And R is ₅₂ A single ring or multiple rings which are capable of being linked to each other to form an alicyclic or aromatic ring, wherein the carbon atoms forming the single ring or multiple rings may be substituted with one or more hetero atoms selected from N, O, P, si, S, ge, se, te;

in the chemical formula D1, A ₃₂ Two carbon atoms adjacent to each other in the ring can be bonded to the structural formula Q ₁₁ Is combined to form a condensed ring,

in the chemical formula D2, the A ₃₁ Two carbon atoms adjacent to each other in the ring can be bonded to the structural formula Q ₁₂ To form a condensed ring, said A ₃₂ Two carbon atoms adjacent to each other in the ring can be bonded to the structural formula Q ₁₁ Is capable of forming a condensed ring,

[ chemical formula D3]

In the above-mentioned [ chemical formula D3],

the X is ₁ Is any one selected from B, P, P =o,

the R is ₆₁ To R ₇₀ Each of which is the same as or different from the other and is independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a cyano group, a halogen groupMeaning one, said R ₆₁ To R ₇₀ Can be combined with one or more rings selected from the group consisting of T1 to T3 to additionally form an alicyclic or aromatic monocyclic ring or polycyclic ring,

In the [ chemical formula D4] and the [ chemical formula D5],

the X is ₂ Is any one selected from B, P, P =o,

t4 to T6 are the same as T1 to T3 in [ formula D3],

the R is ₆₁ To R ₇₅ And [ chemical formula D3]]Said R in (a) ₆₁ To R ₇₀ The same is true of the fact that,

the X is ₃ Is any one selected from B, P, P =o,

t7 to T9 are the same as T1 to T3 in [ formula D3],

the R is ₇₁ R is R ₇₂ Can be linked to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring, or can be combined with the T7 ring or the T9 ring to additionally form an alicyclic or aromatic monocyclic or polycyclic ring,

[ chemical formula D10]

In the [ chemical formula D8] to [ chemical formula D10],

wherein X is any one selected from B, P, P =o,

the substituent R ₃ To R ₅ Respectively with [ chemical formula D3] ]Said R in (a) ₆₁ To R ₇₀ The same is true of the fact that,

if the ring formed by Cy1 has a nitrogen atom removed, Q bonded to the nitrogen atom ₁ An aromatic carbon atom in the ring and Q to be bonded to Cy1 ₁ An aromatic carbon atom in the ring, the remainder being a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms,

in the chemical formula D9 of the present invention,

the "Cy2" can be attached to the Cy1 to form a saturated hydrocarbon ring, and if the carbon atom contained in Cy1 is removed, the remainder is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms formed by the Cy2,

in the chemical formula D10 described above, the chemical formula,

the ring formed by the Cy3 if removed will bind Q to the Cy3 ₃ A ring aromatic carbon atom, Q to be bonded to a nitrogen atom ₃ An internal aromatic carbon atom, a nitrogen atom, a Cy1 internal carbon atom to which the nitrogen atom is bonded, the remainder being a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms,

wherein the "substituted" in the "substituted or unsubstituted" in the [ chemical formula D1] to [ chemical formula D10] means a sulfur-substituted aryl group having 6 to 24 carbon atoms, an aralkyl group having 7 to 24 carbon atoms, an alkylaryl group having 7 to 24 carbon atoms, an heteroaryl group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, a diarylamino group having 12 to 24 carbon atoms, a diheteroarylamino group having 2 to 24 carbon atoms, an aryl (hetero) group having 7 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms, an acyloxy group having 6 to 24 carbon atoms, an arylsilyl group having 6 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, a diarylamino group having 12 to 24 carbon atoms, a diarylamino group having 2 to 24 carbon atoms, an aryl (hetero) having 7 to 24 carbon atoms, an alkylsilyl group having 6 to 24 carbon atoms.

16. The organic light-emitting device according to claim 1, wherein,

the first light emitting layer includes one or more compounds represented by the chemical formula a or the chemical formula B,

an anthracene derivative represented by the following chemical formula E is used as a host in the second light-emitting layer:

[ chemical formula E ]

In the above-mentioned [ formula E ],

17. The organic light-emitting device according to claim 16, wherein,

the anthracene derivative represented by the chemical formula E is an anthracene derivative represented by the following chemical formula E-1 or chemical formula E-2:

[ chemical formula E-1]

[ chemical formula E-2]

In the [ chemical formula E-1] and the [ chemical formula E-2],

18. The organic light-emitting device according to claim 16, wherein,

the anthracene derivative represented by a chemical formula E in the second light emitting layer includes at least one deuterium.

19. The organic light-emitting device according to claim 16, wherein,

in the chemical formula E, R ₄₁ To R ₄₈ At least one of which is deuterium.

20. The organic light-emitting device according to claim 16, wherein,

in the chemical formula E, ar ₅ Is a substituent comprising at least one deuterium.

21. The organic light-emitting device according to claim 16, wherein,

in the chemical formula E, R ₄₉ To R ₅₆ At least one of which is a substituent comprising deuterium.

22. The organic light-emitting device according to claim 16, wherein,

the deuteration degree of the chemical formula E is more than 20%.

23. The organic light-emitting device according to claim 15, wherein,

the first dopant in the first light emitting layer and the second dopant in the second light emitting layer are the same or different, respectively, and any one or more compounds selected from the [ chemical formula D1] to the [ chemical formula D10] are used.

24. The organic light-emitting device according to claim 14, wherein,

The organic light emitting element is used for any one device selected from a flat panel display device, a flexible display device, a device for single-color or white flat panel illumination, and a device for single-color or white flexible illumination.