KR102197236B1 - Organic light emitting device - Google Patents

Abstract

The present specification is a cathode; An anode provided to face the cathode; An emission layer provided between the cathode and the anode; A first organic material layer provided between the cathode and the emission layer and including the compound of Formula 1; And a second organic material layer disposed between the cathode and the first organic material layer and including the compound of Formula 2;

Description

Organic light emitting device {ORGANIC LIGHT EMITTING DEVICE}

The present specification relates to an organic light emitting device.

This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0085933 filed with the Korean Intellectual Property Office on July 24, 2018, the entire contents of which are incorporated herein.

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light emitting device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer has a multilayer structure made of different materials in order to increase the efficiency and stability of the organic light emitting device, and may include, 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 the structure of such an organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls to the ground.

Development of a new material for the organic light emitting device as described above is continuously required.

Korean Patent Publication No. 10-2007-0091540

The present specification provides an organic light emitting device.

An exemplary embodiment of the present specification is a cathode; An anode provided to face the cathode;

An emission layer provided between the cathode and the anode; A first organic material layer provided between the cathode and the emission layer and including a compound represented by the following formula (1); And a second organic material layer provided between the cathode and the first organic material layer and including a compound represented by Formula 2 below.

[Formula 1]

In Formula 1,

X is O or S,

At least one of R1 to R16 is a group represented by the following formula A, and the remainder are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or combined with an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring,

[Formula A]

In the formula A,

At least one of X1 to X3 is N, the rest are CR,

R is hydrogen or a substituted or unsubstituted aromatic hydrocarbon ring combined with -(L2) _l2 -Ar2 or -(L3) _l3 -Ar3; Or to form a substituted or unsubstituted heterocycle,

L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

Ar2 and Ar3 are the same as or different from each other, and each independently a cyano group; A substituted or unsubstituted aryl group; A substituted or unsubstituted silyl group; Or a substituted or unsubstituted heterocyclic group,

l1 to l3 are each independently an integer of 1 to 3,

When l1 is 2 or more, two or more L1s are the same as or different from each other,

When l2 is 2 or more, 2 or more L2s are the same as or different from each other,

When l3 is 2 or more, 2 or more L3s are the same as or different from each other,

는 상기 화학식 1에 결합되는 부위를 의미하며,

Means a moiety bonded to Formula 1,

[Formula 2]

In Formula 2,

L11 to L12 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,

Ar11 to Ar13 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group.

The organic light-emitting device according to the exemplary embodiment of the present specification has an improved ability to inject electrons coming from the cathode, thereby providing a low driving voltage and high luminous efficiency.

1 to 5 illustrate examples of an organic light-emitting device according to an exemplary embodiment of the present specification.

Hereinafter, the present specification will be described in detail.

An exemplary embodiment of the present specification is a cathode; An anode provided to face the cathode;

An emission layer provided between the cathode and the anode; A first organic material layer disposed between the cathode and the emission layer and including the compound represented by Formula 1; And a second organic material layer provided between the cathode and the first organic material layer and including a compound represented by Formula 2 above.

According to the exemplary embodiment of the present specification, the compound of Formula 1 is used in the hole blocking layer in a non-linear structure, so that it is possible to improve the efficiency of the organic light-emitting device, improve the low driving voltage and life characteristics. In addition, since at least one of R1 to R16 in the structure of the compound represented by Formula 1 is Formula A, and Formula A is an electron depletion structure, the dipole moment of the molecule can be designed close to non-polarity. When manufacturing an organic light emitting device including the compound represented by 1 in the hole blocking layer, it is possible to form an amorphous layer. Accordingly, the organic light-emitting device according to the exemplary embodiment of the present specification can improve efficiency, low driving voltage, and improve lifespan characteristics.

In particular, since the compound represented by Formula 1 has a three-dimensionally horizontal structure, electron mobility is enhanced when an organic material layer is formed with such a material.

In the present specification, "energy level" means the energy level. Therefore, the energy level is interpreted to mean the absolute value of the corresponding energy value. For example, when the energy level is low or deep, it means that the absolute value increases in the negative direction from the vacuum level.

In the present specification, HOMO (highest occupied molecular orbital) means a molecular orbital function (highest occupied molecular orbital) in a region with the highest energy in a region where electrons can participate in binding, and LUMO (lowest unoccupied molecular orbital) Means a molecular orbital function (lowest unoccupied molecular orbital) in which electrons have the lowest energy among the anti-bonding regions, and the HOMO energy level means the distance from the vacuum level to the HOMO. In addition, the LUMO energy level means the distance from the vacuum level to the LUMO.

In the present specification, a bandgap means a difference in energy levels between HOMO and LUMO, that is, a HOMO-LUMO gap.

According to an exemplary embodiment of the present specification, the compound represented by Formula 1 may have a HOMO energy level of 6.0 eV or more, a triplet energy level of 2.5 eV or more, and a bandgap of 3.0 eV or more. I can.

As the triplet energy of the compound used for the first organic material layer is higher, the triplet energy of the emission layer is not transferred to an adjacent layer, so that the efficiency of the organic light emitting device can be increased. In addition, since the HOMO energy level of the compound used in the hole blocking layer is 6.0 eV or higher, it is possible to prevent the transmission of holes from the emission layer, thereby making a high-efficiency and long-life device.

Accordingly, when the compound represented by Formula 1 that satisfies the above range is used for the hole blocking layer, electron mobility is high, and when used in an organic light emitting device, the driving voltage is low, and high efficiency and long lifespan are exhibited. In addition, since the LUMO energy level has a value of 3.0 eV to 2.6 eV, the difference in energy level with the light emitting layer is not large, so that electron injection is smooth. The LUMO energy level refers to an energy level in a region having a low energy barrier with the emission layer.

In the present specification, the HOMO energy level can be measured using an atmospheric photoelectron spectroscopy device (manufactured by RIKEN KEIKI Co., Ltd.: AC3), and the LUMO energy level can be calculated as a wavelength value measured through photoluminescence (PL). I can.

According to an exemplary embodiment of the present specification, since the compound represented by Formula 2 is a structure in which a substituted or unsubstituted aryl group is bonded around a triazine core, an organic light emitting device including the same is used to inject electrons and transfer electrons from the cathode. Due to this, the efficiency and lifetime characteristics of the organic light emitting device can be improved. According to an exemplary embodiment of the present specification, the first organic material layer is a hole blocking layer.

According to an exemplary embodiment of the present specification, the second organic silver layer is an electron transport layer, an electron injection layer, or an electron injection and transport layer.

According to an exemplary embodiment of the present specification, the second organic material is an electron injection layer.

According to an exemplary embodiment of the present specification, the second organic material is an electron transport layer.

According to an exemplary embodiment of the present specification, the second organic material is a layer electron injection and transport layer.

According to an exemplary embodiment of the present specification, the first organic material layer is a hole blocking layer, and the hole blocking layer is provided in contact with the emission layer.

According to an exemplary embodiment of the present specification, the first organic material layer is a hole blocking layer, the second organic material is an electron transport layer, an electron injection layer, or an electron injection and transport layer, and the hole blocking layer is provided in contact with the emission layer. .

According to an exemplary embodiment of the present specification, when the first organic material layer includes the compound represented by Formula 1, and the second organic material layer includes the compound represented by Formula 2, Formula 1 has excellent hole blocking ability. Since the above formula (2), which has excellent electron injection and transport capabilities, is simultaneously applied to an organic light emitting device, by controlling the substances included in the electron blocking layer and the electron transport layer (or electron injection and transport layer), the energy level between each layer is adjusted. Driving voltage, efficiency and/or life characteristics can be improved.

When a member is referred to herein as being “on” another member, this includes not only the case where a member is in contact with another member, but also the case where another member exists between the two members.

In the present specification, when a part "includes" a certain component, it means that other components may be further included rather than excluding other components unless specifically stated to the contrary.

Examples of the substituent in the present specification are described below, but are not limited thereto.

The term "substituted" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same or different from each other.

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Hydroxy group; Cyano group; Alkyl group; Cycloalkyl group; Alkenyl group; Alkoxy group; Aryloxy group; Silyl group; Haloalkyl group; Haloalkoxy group; Aryl group; And it means that it is substituted with one or more substituents selected from the group consisting of a heterocyclic group, or is substituted with a substituent to which two or more of the substituents are connected, or does not have any substituents. For example, "a substituent to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, Cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1 ,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are limited thereto. It is not.

In the present specification, the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but it is preferably 1 to 30 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -Hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc., but It is not limited.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it has 10 to 30 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a triphenylenyl group, a pyrenyl group, a phenalenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, etc., but limited thereto. It does not become.

In the present specification, the fluorenyl group may be substituted, and adjacent groups may be bonded to each other to form a ring.

When the fluorenyl group is substituted, it may have the following structure, but is not limited thereto.

In the present specification, the "adjacent" group means a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent positioned three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted. I can. For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, the heterocyclic group includes at least one atom or hetero atom other than carbon, and specifically, the hetero atom may include at least one atom selected from the group consisting of O, N, Se, and S. The number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include thiophenyl group, furanyl group, pyrrolyl group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridinyl group, bipyridinyl group, pyrimidinyl group, triazinyl group, Triazolyl group, acridinyl group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl Group, pyrido indolyl group, isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophenyl group, dibenzothiophenyl group, benzo Furanyl group, phenanthridine, phenanthroline, isoxazolyl group, thiadiazolyl group, phenothiazinyl group, dibenzofuranyl group, dibenzosilolyl group, phenoxathiine group ), phenoxazine, phenothiazine, phenazine, dihydroacridinyl, dihydroindenocarbazolyl, and the like, but are not limited thereto.

In the present specification, the aryl group in the aryloxy group is the same as the example of the aryl group described above. Specifically, the aryloxy group includes a phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3- Biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthracenyloxy group , 2-anthracenyloxy group, 9-anthracenyloxy group, 1-phenanthrenyloxy group, 3-phenanthrenyloxy group, 9-phenanthrenyloxy group, and the like, but are not limited thereto.

In the present specification, the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.

In the present specification, a haloalkyl group means that a halogen group is substituted instead of hydrogen of the alkyl group, and examples of the alkyl group may be applied except that H is a halogen group in the alkyl group. For example, -CF ₃ , -CHF ₂ , -CH ₂ F, and the like, but are not limited thereto.

In the present specification, the haloalkoxy group means that a halogen group is substituted for hydrogen of the alkoxy group, and examples of the alkoxy group may be applied except that H is a halogen group in the alkoxy group. E.g., -OCF _3, -OCHF _2, -OCH ₂ F, etc., but is not limited thereto.

In the present specification, an arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied.

In the present specification, a divalent heterocyclic group means that the heterocyclic group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aforementioned heterocyclic group may be applied.

In the present specification, in a substituted or unsubstituted ring formed by bonding of adjacent groups to each other, "ring" is a substituted or unsubstituted aromatic hydrocarbon ring; Or it means a substituted or unsubstituted heterocycle.

In the present specification, the aromatic hydrocarbon ring may be monocyclic or polycyclic, and may be selected from examples of the cycloalkyl group or aryl group, except that it is not monovalent.

In the present specification, the heterocycle is an atom other than carbon and contains one or more heteroatoms, and specifically, the heterocycle may include one or more atoms selected from the group consisting of O, N, Se, and S. The heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from examples of the heterocyclic group except that it is not monovalent.

According to an exemplary embodiment of the present specification, in Formula 1, X is O.

According to an exemplary embodiment of the present specification, in Formula 1, X is S.

According to an exemplary embodiment of the present specification, Formula 1 is represented by the following Formula 1-1 or 1-2.

[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2,

The definitions of L1 to L3, l1 to l3, Ar1, Ar2 and X1 to X3 are the same as defined in Formula A,

At least one of X4 to X6 is N, and the rest are CR',

R'is hydrogen, or a substituted or unsubstituted aromatic hydrocarbon ring combined with -(L5) _l5 -Ar4 or -(L6) _l6 -Ar5; Or to form a substituted or unsubstituted heterocycle,

L4 to L6 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

Ar4 and Ar5 are the same as or different from each other, and each independently a cyano group; A substituted or unsubstituted aryl group; A substituted or unsubstituted silyl group; Or a substituted or unsubstituted heterocyclic group,

l4 to l6 are each independently an integer of 1 to 3,

When l4 is 2 or more, 2 or more L4s are the same as or different from each other,

When l5 is 2 or more, 2 or more L5s are the same as or different from each other,

When l6 is 2 or more, 2 or more L6 are the same as or different from each other,

n1 is an integer from 0 to 2,

n2 is an integer from 0 to 2,

1 ≤ n1+n2 ≤ 4,

R100 and R101 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or combined with an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring,

r100 and r101 are each independently an integer of 1 to 8,

1≦r100+n1≦8,

1≦r101+n2≦8,

When r100 and r101 are each 2 or more, the structures in the two or more parentheses are the same as or different from each other.

According to an exemplary embodiment of the present specification, in Chemical Formula 1, at least one of R1 to R16 is a group represented by Chemical Formula A, and the others are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or combined with an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring.

According to an exemplary embodiment of the present specification, in Chemical Formula 1, at least one of R1 to R16 is a group represented by Chemical Formula A, and the others are the same as or different from each other, and each independently hydrogen; Alkyl group; It is an aryl group unsubstituted or substituted with an alkyl group, or combines with an adjacent group to form an aromatic hydrocarbon ring.

According to an exemplary embodiment of the present specification, in Chemical Formula 1, at least one of R1 to R16 is a group represented by Chemical Formula A, and the others are the same as or different from each other, and each independently hydrogen; Alkyl group; A phenyl group unsubstituted or substituted with an alkyl group; Biphenyl group; Terphenyl group; Naphthyl group; Triphenylenyl group; Or a fluorenyl group unsubstituted or substituted with an alkyl group, or combine with an adjacent group to form a benzene ring.

According to an exemplary embodiment of the present specification, in Chemical Formula 1, at least one of R1 to R16 is a group represented by Chemical Formula A, and the others are the same as or different from each other, and each independently hydrogen; Methyl group; n-butyl group; t-butyl group; A phenyl group unsubstituted or substituted with a methyl group or a t-butyl group; Biphenyl group; Terphenyl group; Naphthyl group; Triphenylenyl group; Or a fluorenyl group unsubstituted or substituted with a methyl group, or bonded to an adjacent group to form a benzene ring.

According to an exemplary embodiment of the present specification, 1 or 2 of R1 to R16 are the same as or different from each other, and each independently a group represented by Formula A, and 0 to 3 of R1 to R16 are an alkyl group; Aryl group; Or an alkylaryl group, and the rest are hydrogen.

According to an exemplary embodiment of the present specification, at least one of R1 to R16 is a group represented by the following formula A, the rest are the same as or different from each other, and each independently hydrogen; Alkyl group; Aryl group; Or, it is an arylalkyl group, or combines with an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring.

According to an exemplary embodiment of the present specification, groups of R1 to R16 that are not represented by Formula A or form a substituted or unsubstituted aromatic hydrocarbon ring by bonding with adjacent groups are the same as or different from each other, and each independently t- Butylphenyl group; Methyl group; t-butyl group; Phenyl group; Methylphenyl group; n-butyl group; Naphthyl group; Triphenylenyl group; Or 9,9-dimethylfluorenyl group.

According to an exemplary embodiment of the present specification, a group capable of forming an aromatic hydrocarbon ring by bonding with adjacent groups among R1 to R16 is R1 and R2, or R15 and R16. That is, according to an exemplary embodiment of the present specification, in Formula 1, at least one of R1 to R16 is a group represented by Formula A, and the others are the same as or different from each other, and each independently hydrogen; Alkyl group; It is an aryl group substituted or unsubstituted with an alkyl group, or R1 and R2 are bonded to each other to form an aromatic hydrocarbon ring, or R15 and R16 are bonded to each other to form an aromatic hydrocarbon ring. At this time, the aromatic hydrocarbon ring formed by bonding of R1 and R2 to each other may be a benzene ring, and the aromatic hydrocarbon ring formed by bonding of R15 and R16 to each other may be a benzene ring.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are bonded to each other to form an aromatic hydrocarbon ring.

According to an exemplary embodiment of the present specification, in Formula 1, R1 and R2 are bonded to each other to form a benzene ring.

According to an exemplary embodiment of the present specification, in Formula 1, R15 and R16 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring.

According to an exemplary embodiment of the present specification, in Formula 1, R15 and R16 are bonded to each other to form an aromatic hydrocarbon ring.

According to an exemplary embodiment of the present specification, in Formula 1, R15 and R16 are bonded to each other to form a benzene ring.

According to an exemplary embodiment of the present specification, in Formula A, L1 to L3 are the same as or different from each other, and each independently a direct bond; An arylene group unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group; Or an alkyl group, an aryl group, a heterocyclic group, and a divalent heterocyclic group unsubstituted or substituted with one or more substituents selected from the group consisting of an aryl group substituted with an alkyl group.

According to an exemplary embodiment of the present specification, in Formula A, L1 to L3 are the same as or different from each other, and each independently a direct bond; A phenyl group unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group; A biphenylene group unsubstituted or substituted with a heterocyclic group; Naphthylene group; A divalent fluorenyl group unsubstituted or substituted with an alkyl group; Divalent terphenyl group; A divalent pyridinyl group unsubstituted or substituted with a heterocyclic group; Divalent furanyl group; Divalent thiophenyl group; Divalent dibenzofuranyl group; Divalent dibenzothiophenyl group; A divalent carbazolyl group unsubstituted or substituted with an aryl group or an aryl group substituted with an alkyl group; A dihydroindenocarbazolyl group unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group and an aryl group; A divalent benzocarbazolyl group unsubstituted or substituted with an aryl group or an aryl group substituted with an alkyl group; A divalent dibenzosilolyl group unsubstituted or substituted with an alkyl group; Divalent phenoxanthynyl group; A divalent phenoxazinyl group; Divalent phenothiazinyl group; Or a divalent phenazinyl group.

According to an exemplary embodiment of the present specification, in Formula A, L1 to L3 are the same as or different from each other, and each independently a direct bond; A phenyl group unsubstituted or substituted with a methyl group, a phenyl group, a pyridinyl group, a carbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl group; A biphenylene group unsubstituted or substituted with a pyridinyl group; Naphthylene group; A divalent fluorenyl group unsubstituted or substituted with a methyl group; Divalent terphenyl group; A divalent pyridinyl group unsubstituted or substituted with a pyridinyl group; Divalent furanyl group; Divalent thiophenyl group; Divalent dibenzofuranyl group; Divalent dibenzothiophenyl group; A divalent carbazolyl group unsubstituted or substituted with a phenyl group or a phenyl group substituted with a methyl group; A dihydroindenocarbazolyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a methyl group and a phenyl group; A divalent benzocarbazolyl group unsubstituted or substituted with a phenyl group or a biphenyl group substituted with a methyl group; A divalent dibenzosilolyl group unsubstituted or substituted with a methyl group; Divalent phenoxanthynyl group; A divalent phenoxazinyl group; Divalent phenothiazinyl group; Or a divalent phenazinyl group.

According to an exemplary embodiment of the present specification, in Formula A, L1 is a direct bond; An arylene group unsubstituted or substituted with an alkyl group or an aryl group; Or an alkyl group, an aryl group, or a divalent heterocyclic group unsubstituted or substituted with an aryl group substituted with an alkyl group.

According to an exemplary embodiment of the present specification, in Formula A, L1 is a direct bond; A phenyl group unsubstituted or substituted with an alkyl group or an aryl group; Biphenylene group; Naphthylene group; A divalent fluorenyl group unsubstituted or substituted with an alkyl group; Divalent pyridinyl group; Divalent furanyl group; Divalent thiophenyl group; Divalent dibenzofuranyl group; Divalent dibenzothiophenyl group; A divalent carbazolyl group unsubstituted or substituted with an aryl group or an aryl group substituted with an alkyl group; A dihydroindenocarbazolyl group unsubstituted or substituted with an alkyl group; A divalent benzocarbazolyl group unsubstituted or substituted with an aryl group or an aryl group substituted with an alkyl group; A divalent dibenzosilolyl group unsubstituted or substituted with an alkyl group; Divalent phenoxanthynyl group; A divalent phenoxazinyl group; Or a divalent phenothiazinyl group.

According to an exemplary embodiment of the present specification, in Formula A, L1 is a direct bond; A phenyl group unsubstituted or substituted with a methyl group or a phenyl group; Biphenylene group; Naphthylene group; A divalent fluorenyl group unsubstituted or substituted with a methyl group; Divalent pyridinyl group; Divalent furanyl group; Divalent thiophenyl group; Divalent dibenzofuranyl group; Divalent dibenzothiophenyl group; A divalent carbazolyl group unsubstituted or substituted with a phenyl group or a phenyl group substituted with a methyl group; A dihydroindenocarbazolyl group unsubstituted or substituted with a methyl group; A divalent benzocarbazolyl group unsubstituted or substituted with a phenyl group or a biphenyl group substituted with a methyl group; A divalent dibenzosilolyl group unsubstituted or substituted with a methyl group; A divalent phenocate-zinyl group; A divalent phenoxazinyl group; Or a divalent phenothiazinyl group.

According to an exemplary embodiment of the present specification, in Formula A, L2 and L3 are the same as or different from each other, and each independently a direct bond; An arylene group unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group; Or an alkyl group, an aryl group, a heterocyclic group, and a divalent heterocyclic group unsubstituted or substituted with one or more substituents selected from the group consisting of an aryl group substituted with an alkyl group.

According to an exemplary embodiment of the present specification, in Formula A, L2 and L3 are the same as or different from each other, and each independently a direct bond; A phenyl group unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group; A biphenylene group unsubstituted or substituted with a heterocyclic group; Divalent terphenyl group; A divalent pyridinyl group unsubstituted or substituted with a heterocyclic group; Divalent dibenzofuranyl group; Divalent dibenzothiophenyl group; A divalent carbazolyl group unsubstituted or substituted with an aryl group; A dihydroindenocarbazolyl group unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group and an aryl group; Or a divalent phenazinyl group.

According to an exemplary embodiment of the present specification, in Formula A, L2 and L3 are the same as or different from each other, and each independently a direct bond; A phenyl group unsubstituted or substituted with a methyl group, a phenyl group, a pyridinyl group, a carbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl group; A biphenylene group unsubstituted or substituted with a pyridinyl group; Divalent terphenyl group; A divalent pyridinyl group unsubstituted or substituted with a pyridinyl group; Divalent dibenzofuranyl group; Divalent dibenzothiophenyl group; A divalent carbazolyl group unsubstituted or substituted with a phenyl group; A dihydroindenocarbazolyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a methyl group and a phenyl group; Or a divalent phenazinyl group.

According to an exemplary embodiment of the present specification, in Formula A, l1 is 1.

According to an exemplary embodiment of the present specification, in Formula A, l1 is 2.

According to an exemplary embodiment of the present specification, in Formula A, l1 is 3.

According to an exemplary embodiment of the present specification, in Formula A, l2 is 1.

According to an exemplary embodiment of the present specification, in Formula A, l2 is 2.

According to an exemplary embodiment of the present specification, in Formula A, l2 is 3.

According to an exemplary embodiment of the present specification, in Formula A, l3 is 1.

According to an exemplary embodiment of the present specification, in Formula A, l3 is 2.

According to an exemplary embodiment of the present specification, in Formula A, l3 is 3.

일 수 있으며, 연결 구조는 이에 한정 되는 것은 아니다.According to an exemplary embodiment of the present specification, in Formula A, when l1 is 2 or more, l1 is connected in a series structure. For example, L1 is a divalent carbazolyl group; Or a phenylene group, and when l1 is 2,

It may be, and the connection structure is not limited thereto.

일 수 있으며, 연결 구조는 이에 한정 되는 것은 아니다.According to an exemplary embodiment of the present specification, in Formula 1, when l1 is 2 or more, l1 is connected in a series structure. For example, L1 is a divalent carbazolyl group; Or a phenylene group, and when l1 is 3,

It may be, and the connection structure is not limited thereto.

According to an exemplary embodiment of the present specification, in Formula A, at least one of X1 to X3 is N, and the rest are CR.

According to an exemplary embodiment of the present specification, in Formula A, at least one of X1 to X3 is N, and the rest are CR.

According to an exemplary embodiment of the present specification, in Formula A, X1 is N, and X2 and X3 are each independently CR.

According to an exemplary embodiment of the present specification, in Formula A, X2 is N, and X1 and X3 are each independently CR.

According to an exemplary embodiment of the present specification, in Formula A, X3 is N, and X1 and X2 are each independently CR.

According to an exemplary embodiment of the present specification, in Formula A, X1 and X2 are N, and X3 are each independently CR.

According to an exemplary embodiment of the present specification, in Formula A, X1 and X3 are N, and X2 are each independently CR.

According to an exemplary embodiment of the present specification, in Formula A, X2 and X3 are N, and X1 is CR.

According to an exemplary embodiment of the present specification, in Formula A, X1 to X3 are N.

According to an exemplary embodiment of the present specification, R is hydrogen, or is combined with -(L2) _l2 -Ar2 or -(L3) _l3 -Ar3 to form a substituted or unsubstituted aromatic hydrocarbon ring.

According to an exemplary embodiment of the present specification, R is hydrogen, or is combined with -(L2) _l2 -Ar2 or -(L3) _l3 -Ar3 to form an aromatic hydrocarbon ring unsubstituted or substituted with a heterocyclic group.

According to an exemplary embodiment of the present specification, R is hydrogen, or is combined with -(L2) _l2 -Ar2 or -(L3) _l3 -Ar3 to form a benzene ring unsubstituted or substituted with a heterocyclic group.

According to an exemplary embodiment of the present specification, R is hydrogen, or is combined with -(L2) _l2 -Ar2 or -(L3) _l3 -Ar3 to form a benzene ring unsubstituted or substituted with a benzocarbazole group.

According to an exemplary embodiment of the present specification, in Formula A, Ar2 and Ar3 are the same as or different from each other, and each independently a cyano group; An aryl group unsubstituted or substituted with a cyano group, an alkyl group, a haloalkyl group, a haloalkoxy group, or a heteroaryl group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; Or an alkyl group, or a heterocyclic group unsubstituted or substituted with an aryl group.

According to an exemplary embodiment of the present specification, in Formula A, Ar2 and Ar3 are the same as or different from each other, and each independently a cyano group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; A phenyl group unsubstituted or substituted with a cyano group, an alkyl group or a haloalkyl group; A cyano group or a biphenyl group unsubstituted or substituted with a haloalkyl group; Naphthyl group; A terphenyl group unsubstituted or substituted with a cyano group, a haloalkyl group, a haloalkoxy group, or a heterocyclic group; A fluorenyl group unsubstituted or substituted with an alkyl group; Phenanthrenyl group; Triphenylenyl group; Fluoranthenyl group; Phenalenyl group; Pyridinyl group; Dibenzofuranyl group unsubstituted or substituted with an alkyl group; Dibenzothiophenyl group; A carbazolyl group unsubstituted or substituted with an alkyl group or an aryl group; Benzocarbazolyl group; Dibenzosilolyl group unsubstituted or substituted with an alkyl group; Phenoxazinyl group; Phenothiazinyl group; Phenoxanthinyl group; Pyridoindolyl group; Quinolinyl group; Dihydroindenocarbazolyl group unsubstituted or substituted with an alkyl group; Or a dihydroacridinyl group unsubstituted or substituted with an alkyl group.

According to an exemplary embodiment of the present specification, in Formula A, Ar2 and Ar3 are the same as or different from each other, and each independently a cyano group; A silyl group unsubstituted or substituted with a methyl group or a phenyl group; A cyano group, a methyl group, or a phenyl group unsubstituted or substituted with -CF ₃ ; A cyano group, or a biphenyl group unsubstituted or substituted with -CF ₃ ; Naphthyl group; A terphenyl group unsubstituted or substituted with a cyano group, -CF ₃ , -OCF ₃ , or a pyridinyl group; A fluorenyl group unsubstituted or substituted with a methyl group; Phenanthrenyl group; Triphenylenyl group; Fluoranthenyl group; Phenalenyl group; Pyridinyl group; A dibenzofuranyl group unsubstituted or substituted with a methyl group; Dibenzothiophenyl group; A carbazolyl group unsubstituted or substituted with a methyl group, a phenyl group, or a biphenyl group; Benzocarbazolyl group; Dibenzosilolyl group unsubstituted or substituted with a methyl group; Phenoxazinyl group; Phenothiazinyl group; Phenoxanthinyl group; Pyridoindolyl group; Quinolinyl group; Dihydroindenocarbazolyl group unsubstituted or substituted with a methyl group; Or a dihydroacridinyl group unsubstituted or substituted with a methyl group.

According to an exemplary embodiment of the present specification, Formula A is represented by any one of the following Formulas A-1 to A-3.

[Formula A-1]

[Formula A-2]

[Formula A-3]

In the formulas A-1 to A-3,

The definitions of L1 and l1 are as defined in Formula A,

X11 is N or CH, X12 is N or CH, X13 is N or CH, and at least two of X11 to X13 are N,

Ar21 to Ar24 are the same as or different from each other, and each independently one substituent selected from the group consisting of'cyano group, halogen group, alkyl group, alkoxy group, aryl group, trialkylsilyl group, triarylsilyl group and heterocyclic group' An aryl group substituted with, substituted with a substituent connected with two groups selected from the group, or substituted with a substituent connected with three groups selected from the group, or unsubstituted; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; Or a heterocyclic group substituted or unsubstituted with one or more substituents selected from the group consisting of ‘alkyl group, aryl group, alkylaryl group, heteroarylaryl group and heterocyclic group’,

R50 and R51 are the same as or different from each other, and each independently hydrogen; Alkyl group; Aryl group; Or a heteroaryl group,

a50 is an integer from 0 to 4, and when a50 is 2 or more, R50 is the same as or different from each other,

a51 is an integer of 0 to 4, and when a51 is 2 or more, R51 is the same as or different from each other.

According to an exemplary embodiment of the present specification, L1 is a direct bond; An arylene group unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group; Or a divalent heterocyclic group unsubstituted or substituted with an alkyl group, an alkylaryl group or an aryl group.

According to an exemplary embodiment of the present specification, L1 is a direct bond; C1~6 alkyl group, C6~20 aryl group or C2~20 heteroaryl group substituted or unsubstituted C6~18 arylene group; Or a C1~6 alkyl group, a C6~20 alkylaryl group, or a C6~20 aryl group substituted or unsubstituted divalent C2~20 heterocyclic group.

According to an exemplary embodiment of the present specification, L1 is a direct bond; A C6~13 arylene group unsubstituted or substituted with a C1~6 alkyl group, a C6~12 aryl group, or a C2~12 heteroaryl group; Or a C1~6 alkyl group, a C6~16 alkylaryl group, or a C6~15 aryl group substituted or unsubstituted divalent C2~16 heterocyclic group.

;

;

; 또는 메틸기 또는 페닐기로 치환 또는 비치환된 2가의 플루오레닐기이다.According to an exemplary embodiment of the present specification, L1 is a direct bond; A phenylene group unsubstituted or substituted with a methyl group or a phenyl group; Biphenylene group; Divalent naphthyl group; Divalent furanyl group; Divalent thiophenyl group; Divalent pyridinyl group; Divalent dibenzofuranyl group; Divalent dibenzothiophenyl group; A divalent carbazolyl group unsubstituted or substituted with a methylphenyl group or a phenyl group; A biphenyl group substituted with a methyl group or a divalent benzocarbazolyl group unsubstituted or substituted with a phenyl group; A divalent indenocarbazolyl group unsubstituted or substituted with a methyl group; A divalent dibenzosilolyl group unsubstituted or substituted with a methyl group;

;

;

; Or a divalent fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group.

According to an exemplary embodiment of the present specification, Ar21 to Ar24 are the same as or different from each other, and each independently a trialkylsilyl group; Triarylsilyl group; The group consisting of a cyano group, a haloalkyl group, a haloalkoxy group, a trialkylsilyl group, a triarylsilyl group, an alkyl group, an aryl group, and a heterocyclic group unsubstituted or substituted with'alkyl group, alkylaryl group, aryl group or heterocyclic group' An aryl group unsubstituted or substituted with one or more substituents selected from; Or an alkyl group, a heteroaryl aryl group, an aryl group, and a heterocyclic group unsubstituted or substituted with one or more substituents selected from the group consisting of a heterocyclic group.

According to an exemplary embodiment of the present specification, Ar21 to Ar24 are the same as or different from each other, and each independently a triphenylsilyl group; Dibenzofuranyl group unsubstituted or substituted with trifluoromethyl group, trifluoromethoxy group, trimethylsilyl group, methyl group, biphenyl group, triphenylenyl group, fluoranthenyl group,'methyl group, phenyl group, or dibenzofuranyl group' , Dibenzothiophenyl group, carbazolyl group,'methyl group, phenyl group, biphenyl group or triphenylenyl group substituted or unsubstituted carbazolyl group, benzocarbazolyl group, phenyl group or pyridinyl group substituted or unsubstituted pyridine A phenyl group unsubstituted or substituted with an indenocarbazolyl group, a dimethyldibenzosilolyl group, or a quinolinyl group substituted or unsubstituted with a nil group, a methyl group, or a dimethylphenyl group; A biphenyl group unsubstituted or substituted with a cyano group, a haloalkyl group, a trimethylsilyl group, a triphenylsilyl group, a pyridinyl group, or a carbazolyl group; A naphthyl group unsubstituted or substituted with a phenyl group; Benzocarbazolyl group; Dibenzofuranyl group; Dibenzothiophenyl group; A carbazolyl phenyl group or a carbazolyl group unsubstituted or substituted with a phenyl group; Terphenyl group unsubstituted or substituted with a pyridinyl group; A fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; Phenalenyl group; Phenanthrenyl group; Or a triphenylenyl group, or any one selected from the following structures.

According to an exemplary embodiment of the present specification, R50 and R51 are the same as or different from each other, and each independently a heteroaryl group.

According to an exemplary embodiment of the present specification, R50 and R51 are the same as or different from each other, and each independently a benzocarbazolyl group.

According to an exemplary embodiment of the present specification, the compound represented by Formula 1 is selected from the following compounds.

According to an exemplary embodiment of the present specification, in Formula 2, L11 to L13 are the same as or different from each other, and each independently a direct bond; Or an alkyl group, or an arylene group unsubstituted or substituted with an aryl group.

According to an exemplary embodiment of the present specification, in Formula 2, L11 to L13 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylene group; Naphthylene group; A divalent phenanthrenyl group; Or an alkyl group or a divalent fluorenyl group unsubstituted or substituted with an aryl group.

According to an exemplary embodiment of the present specification, in Formula 2, L11 to L13 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylene group; Naphthylene group; A divalent phenanthrenyl group; Or a methyl group or a divalent fluorenyl group unsubstituted or substituted with a phenyl group.

According to an exemplary embodiment of the present specification, in Formula 2, Ar11 to Ar13 are the same as or different from each other, and each independently substituted with one or more substituents selected from the group consisting of an alkyl group, an aryl group, and an aryl group substituted with an alkyl group, or It is an unsubstituted aryl group.

According to an exemplary embodiment of the present specification, in Formula 2, Ar11 to Ar13 are the same as or different from each other, and each independently substituted with one or more substituents selected from the group consisting of an alkyl group, an aryl group, and an aryl group substituted with an alkyl group, or Unsubstituted fluorenyl group; Benzofluorenyl group unsubstituted or substituted with an alkyl group; Cyclopentane fluorenyl group; Or an indenophenanthrenyl group unsubstituted or substituted with an alkyl group.

According to an exemplary embodiment of the present specification, in Formula 2, Ar11 to Ar13 are the same as or different from each other, and each independently a methyl group, t-butyl group, phenyl group, biphenyl group, naphthyl group, and a phenyl group substituted with a methyl group. A fluorenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of; A benzofluorenyl group unsubstituted or substituted with a methyl group; Cyclopentane fluorenyl group; Or an indenophenanthrenyl group unsubstituted or substituted with a methyl group.

According to an exemplary embodiment of the present specification, L11 is a direct bond, and Ar11 is a C6-14 aryl group.

According to an exemplary embodiment of the present specification, -L11-Ar11 is a phenyl group; Biphenyl group; Naphthyl group; Or a phenanthrenyl group.

According to an exemplary embodiment of the present specification, -L11-Ar11 is a phenyl group; (1,1'-biphenyl)-4-yl group; Naphthalen-1-yl group; Naphthalen-2-yl group; Or phenanthrene-9-yl.

According to an exemplary embodiment of the present specification, -L12-Ar12 is (1,1'-biphenyl)-4-yl group; (1,1'-biphenyl)-3-yl group; (1,1'-biphenyl)-2-yl group; (1,1':4',1"-terphenyl)4-yl group; (1,1':3',1"-terphenyl)-5'-yl group; (1,1':3',1"-terphenyl)-4'-yl group; (1,1':3',1"-terphenyl)-2'-yl group; Naphthalen-2-yl group; Naphthalen-1-yl group; Phenanthrene-9-diary; Phenanthren-2-yl group; Phenanthrene-3-yl group; 4-(naphthalen-2-yl)phenyl group; 3-(naphthalen-1-yl)phenyl group; 2-(naphthalen-2-yl)phenyl group; 4-(phenanthren-2-yl)phenyl group; 4'-(naphthalen-1-yl)-(1,1'-biphenyl-4-yl group; 6-(naphthalen-2-yl) naphthalen-2-yl group; 7-phenylnaphthalen-2-yl group; 6- Phenylnaphthalen-2-yl group; 4-phenylnaphthalen-1-yl group; 10-phenylphenanthrene-9-yl group; 3-(naphthalen-1-yl)phenyl group; 3-(naphthalen-2-yl)phenyl group; 2- (Naphthalen-2-yl)phenyl group; 2-(naphthalen-1-yl)phenyl group; 2-(phenanthren-9-yl)phenyl group; 4-(phenanthren-2-yl)phenyl group; 4-(naphthalene-2) -Yl)-2-phenylphenyl-1-yl group; 4-(naphthalen-1-yl)-2-phenylphenyl-1-yl group; 10-phenylphenanthrene-9-yl group; 7-phenylphenanthrene-3- Diary; or (2,4,6-triphenyl)phenyl group.

According to an exemplary embodiment of the present specification, L12 is a direct bond, and Ar12 is a C10 ~ 30 aryl group.

According to an exemplary embodiment of the present specification, L12 is a direct bond, and Ar12 is a C10 to 24 aryl group.

According to an exemplary embodiment of the present specification, L12 is a direct bond, and Ar12 is a phenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; A biphenyl group unsubstituted or substituted with a phenyl group or a naphthyl group; A naphthyl group unsubstituted or substituted with a phenyl group or a phenanthrenyl group; Or a phenanthrenyl group unsubstituted or substituted with a phenyl group or a naphthyl group.

According to an exemplary embodiment of the present specification, L12 is a direct bond, and Ar12 is a phenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; A biphenyl group unsubstituted or substituted with a phenyl group or a naphthyl group; A naphthyl group unsubstituted or substituted with a phenyl group or a phenanthrenyl group; Or a phenyl group or a phenanthrenyl group unsubstituted or substituted with a naphthyl group, and Ar12 has 10 to 24 carbon atoms.

According to an exemplary embodiment of the present specification, L13 is a direct bond; Phenylene group; Biphenylene group; Naphthylene group; (Phenylene-naphthylene) group; Or a phenanthrenylene group.

According to an exemplary embodiment of the present specification, Ar13 is the following Chemical Formula 13-1.

[Chemical Formula 13-1]

In Formula 13-1,

G ₁ and G ₂ are the same as or different from each other, and each independently hydrogen; Alkyl group; Aryl group; Or an alkylaryl group, G ₁ and G ₂ are spiro bonded to each other to the cyclopentane (cyclopentane) ring; Or to form an indene ring,

g1 is 0 or 1,

g2 is 0 or 1,

Formula 13-1 may be further substituted by G _3, G ₃ is an alkyl group; Or an aryl group.

According to an exemplary embodiment of the present specification, Ar13 is any one selected from the following structures.

In the above structures,

G ₁ and G ₂ are the same as or different from each other, and each independently hydrogen; Alkyl group; Aryl group; Or an alkylaryl group,

The structure may be further substituted by G _3, G ₃ is an alkyl group; Or an aryl group.

According to an exemplary embodiment of the present specification, Ar13 is any one selected from the following structures.

In the above structures,

G ₁ and G ₂ are the same as or different from each other, and each independently hydrogen; Alkyl group; Aryl group; Or an alkylaryl group,

The structure may be further substituted by G _3, G ₃ is an alkyl group; Or an aryl group.

In the exemplary embodiment of the present specification, G ₁ and G ₂ are the same as or different from each other, and each independently hydrogen; C1-6 alkyl group; C6-16 aryl group; Or it is a C7-15 alkylaryl group.

In the exemplary embodiment of the present specification, G ₁ and G ₂ are the same as or different from each other, and each independently hydrogen; Methyl group; Phenyl group; 4-methylphenyl group; Or a biphenyl group.

In the exemplary embodiment of the present specification, G ₃ is an aryl group of a C1 to 6 alkyl group C6 to 12.

In the exemplary embodiment of the present specification, G ₃ is a phenyl group; t-butyl group; Or a naphthyl group.

According to an exemplary embodiment of the present specification, the substituents -L11-Ar11, -L12-Ar12, and -L13-Ar13 of Formula 2 are selected from the following structures.

According to an exemplary embodiment of the present specification, the emission layer includes a host and a dopant, and a maximum emission wavelength of the dopant is in a range of 420 nm to 520 nm.

According to an exemplary embodiment of the present specification, the dopant is a blue fluorescent dopant.

In the present specification, the organic light-emitting device includes a first organic material layer including a compound represented by Formula 1 between the cathode and the emission layer, and a second including the compound represented by Formula 2 between the cathode and the first organic material layer An organic light-emitting device including an organic material layer is a blue organic light-emitting device and has an effect of improving the life of an organic light-emitting device emitting blue light.

According to the exemplary embodiment of the present specification, the host may include one or more materials.

According to an exemplary embodiment of the present specification, the host includes at least one of compounds represented by the following Formulas 3-1 and 3-2. When the following compounds are included, energy levels of the organic material layer and the light-emitting layer are appropriately formed, and since it is easy to control the amount of electrons moving from the organic material layer to the light-emitting layer, the lifespan of the organic light-emitting device is improved.

[Formula 3-1]

[Chemical Formula 3-2]

In Formulas 3-1 and 3-2,

L31 to L35 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

Ar31 to Ar35 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R200 and R201 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted aryl group,

r200 is an integer from 1 to 8,

r201 is an integer from 1 to 7,

When r200 is 2 or more, 2 or more R200s are the same as or different from each other,

When r201 is 2 or more, two or more R201s are the same as or different from each other.

According to an exemplary embodiment of the present specification, L31 to L35 are the same as or different from each other, and each independently a direct bond; Or an arylene group.

According to an exemplary embodiment of the present specification, L31 to L35 are the same as or different from each other, and each independently a direct bond; Phenylene group; Naphthylene group; Or a divalent anthracenyl group.

According to an exemplary embodiment of the present specification, Ar31 to Ar35 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with deuterium; Or a heterocyclic group unsubstituted or substituted with an aryl group.

According to an exemplary embodiment of the present specification, Ar31 to Ar35 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium; Biphenyl group; Naphthyl group; A thiophenyl group unsubstituted or substituted with a phenyl group; Dibenzofuranyl group; Dibenzothiophenyl group; Benzo[b]naphtho[1,2-d]furanyl group; Benzo[b]naphtho[2,3-d]furanyl group; Or a benzo[d]naphtho[1,2-b]furanyl group.

According to an exemplary embodiment of the present specification, R200 is hydrogen; Or an aryl group unsubstituted or substituted with an aryl group.

According to an exemplary embodiment of the present specification, R200 is hydrogen; Or a phenyl group substituted or unsubstituted naphthyl group.

According to an exemplary embodiment of the present specification, R201 is hydrogen.

According to an exemplary embodiment of the present specification, the host is any one or more selected from the following compounds.

According to an exemplary embodiment of the present specification, the compounds of Formulas 1 and 2 may be prepared using starting materials and reaction conditions known in the art. The type and number of substituents can be determined by appropriately selecting a known starting material by a person skilled in the art. In addition, the compounds of Formulas 1 to 3 may be obtained from commercially available ones.

In the exemplary embodiment of the present specification, the organic light emitting device may include two or more light emitting layers. The two or more light emitting layers may be provided in contact with each other, or may be provided by including an additional organic material layer between the two light emitting layers.

In the exemplary embodiment of the present specification, the organic light-emitting device includes two or more light-emitting layers, and includes a charge generation layer between two adjacent light-emitting layers among the two or more light-emitting layers, and the charge-generation layer is an n-type organic material layer and p It may include a type organic material layer.

In another exemplary embodiment, the n-type organic material layer and the p-type organic material layer included in the charge generation layer are NP-junctioned.

In the exemplary embodiment of the present specification, the p-type organic material layer is selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, and an emission layer, and the n-type organic material layer is an electron transport layer, an electron injection layer, a hole blocking layer, and a light emitting layer. It is selected from the group consisting of.

In this specification, n-type means n-type semiconductor properties. In other words, n-type is a property of injecting or transporting electrons through an energy level of LUMO (lowest unoccupied molecular orbital), which can be defined as a property of a material in which the mobility of electrons is greater than that of holes. Conversely, p-type refers to p-type semiconductor properties. In other words, the p-type is a property of injecting or transporting holes through the highest occupied molecular orbital (HOMO) energy level, and this can be defined as a property of a material having a hole mobility greater than that of an electron. In the present specification, the compound or organic material layer having n-type properties may be referred to as an n-type compound or an n-type organic material layer. Further, the compound or organic material layer having p-type properties may be referred to as a p-type compound or a p-type organic material layer. In addition, n-type doping may mean that it has been doped to have n-type characteristics.

In the present specification, the charge generation layer is a layer that generates electric charge without application of an external voltage, and generates electric charge between adjacent emission layers among two or more emission layers so that at least two emission layers included in the organic light emitting device emit light. .

In the present specification, the NP junction may mean not only physical contact between the second electron transport layer, which is an n-type organic material layer, and the p-type organic material layer, but also an interaction capable of easily generating and transporting holes and electrons.

According to the exemplary embodiment of the present specification, when the NP junction is formed, holes or electrons may be easily formed by an external voltage or light source. Accordingly, it is possible to prevent an increase in driving voltage for injection of holes.

In another exemplary embodiment, the maximum emission wavelengths of at least two of the two or more light emitting layers are the same or different from each other.

In the present specification, the maximum emission wavelength means the wavelength at the maximum value of the spectral distribution.

In the exemplary embodiment of the present specification, the maximum emission wavelengths of at least two of the two or more emission layers are different from each other.

In one embodiment of the present specification, at least one of the two or more light emitting layers includes a phosphorescent dopant, and at least one includes a fluorescent dopant.

As in the exemplary embodiment of the present specification, including two or more different light emitting layers from each other, stacking of blue fluorescence, green phosphorescence, and red phosphorescence; A white light-emitting device can be manufactured by stacking blue fluorescence and green-yellow phosphorescence. Specifically, the organic light emitting device according to the exemplary embodiment of the present specification may include a fluorescence emission layer and/or a phosphorescence emission layer.

For example, in the case of blue, the peak wavelength of the photoluminescence spectrum is 400 nm to 500 nm, in the case of green, the peak wavelength of the photoluminescence spectrum is 510 nm to 580 nm, and in the case of red, the peak wavelength of the photoluminescence spectrum is 610 In the range of nm to 680 nm, those skilled in the art may use one layer or a combination of two or more layers of light-emitting layers having different peak wavelengths, if necessary.

In the present specification, the phosphorescent dopant and the fluorescent dopant may be a dopant generally used in the art.

In the exemplary embodiment of the present specification, the organic light emitting device includes: a first light emitting layer provided between the anode and the first organic material layer; And a second emission layer provided on the first emission layer.

In this case, the first emission layer and the second emission layer may be provided in contact with each other, and an additional organic material layer may be provided between the first emission layer and the second emission layer.

In another exemplary embodiment of the present specification, the organic light-emitting device includes: a first light-emitting layer provided in a portion between the anode and the first organic material layer; And a second emission layer provided on the remaining part between the anode and the first organic material layer. An insulating structure may be included between the first emission layer and the second emission layer.

In this case, the first emission layer and the second emission layer may be provided side by side on the same surface of the first organic material layer. In one embodiment, one side of the first emission layer and one side of the second emission layer may be provided in contact with each other.

In the exemplary embodiment of the present specification, the first emission layer and the second emission layer provided side by side may be provided in contact with the same surface of the first organic material layer.

In another exemplary embodiment, an additional layer may be provided between the first emission layer provided side by side and the second emission layer and the first organic material layer.

According to an exemplary embodiment of the present specification, the organic light-emitting device includes: a first light-emitting layer provided between the anode and the first organic material layer; And a second emission layer provided on the first emission layer, and a third emission layer provided on the second emission layer.

In this case, the first emission layer, the second emission layer, and the third emission layer may be provided in contact with each other, and between the first emission layer and the second emission layer and/or between the second emission layer and the third emission layer. An additional organic material layer may be provided.

In another exemplary embodiment, the maximum emission wavelengths of the first emission layer, the second emission layer, and the third emission layer are different from each other.

In another exemplary embodiment, the maximum emission wavelengths of the first emission layer, the second emission layer, and the third emission layer are the same.

In another exemplary embodiment, the first emission layer, the second emission layer, and the third emission layer may include a blue fluorescent dopant, and a maximum emission wavelength of the dopant may be in the range of 420 nm to 520 nm.

For example, the structure of the organic light emitting device according to the present invention may have a structure as shown in FIGS. 1 to 5, but is not limited thereto.

1, an anode 201, a hole transport layer 301, an emission layer 401, a hole blocking layer 701, an electron transport layer 501, and a cathode 601 are sequentially stacked on a substrate 101. The structure is illustrated. In FIG. 1, the hole blocking layer 701 may be a first organic material layer, and the electron transport layer 501 may be the second organic material layer. In addition, a hole injection layer may be additionally provided between the anode 201 and the hole transport layer 301, and FIG. 2 shows that the hole injection layer is additionally provided. 2, an anode 201, a hole injection layer 801, a hole transport layer 301, a light emitting layer 401, a hole blocking layer 701, an electron transport layer 501 and a cathode 601 are sequentially formed on the substrate 101. The structure of the stacked organic light emitting device is illustrated. In FIG. 2, the hole blocking layer 701 may be a first organic material layer, and the electron transport layer 501 may be the second organic material layer.

3, an anode 201, a hole transport layer 301, a first emission layer 402, a second emission layer 403, a hole blocking layer 701, an electron transport layer 501 and a cathode 601 on the substrate 101. The structure of the sequentially stacked organic light emitting devices is illustrated. In FIG. 3, the hole blocking layer 701 is a first organic material layer, the electron transport layer 501 may be the second organic material layer, and the second emission layer 402 and the first emission layer 403 are provided in contact with each other. May be, and an additional organic material layer may be provided.

In FIG. 4, an anode 201 and a hole transport layer 301 are provided on a substrate 101, a first emission layer 402 and a second emission layer 403 are provided on the hole transport layer 301, and the first A structure of an organic light emitting diode in which a hole blocking layer 701, an electron transport layer 501, and a cathode 601 are sequentially stacked on the emission layer 402 and the second emission layer 403 is illustrated. In FIG. 3, the hole blocking layer 701 may be a first organic material layer, and the electron transport layer 501 may be the second organic material layer.

5 shows an anode 201, a hole transport layer 301, a first emission layer 402, a second emission layer 403, a third emission layer 404, a hole blocking layer 701, and an electron transport layer on the substrate 101. A structure of an organic light-emitting device in which 501 and cathode 601 are sequentially stacked is illustrated. In FIG. 5, the hole blocking layer 701 may be a first organic material layer, and the electron transport layer 501 may be the second organic material layer, and the first emission layer 402, the second emission layer 403, and the second emission layer 403 3 The emission layers 404 may be provided in contact with each other, and are added between the first emission layer 402 and the second emission layer 403 and/or between the second emission layer 403 and the third emission layer 404 An organic material layer of may be provided.

1 to 5 are exemplary structures according to the exemplary embodiment of the present specification, and may further include another organic material layer. In addition, in FIGS. 1 to 5, the first organic material layer may be an electron injection layer or an electron injection and transport layer instead of the electron transport layer 501.

The organic light-emitting device of the present specification includes a first organic material layer including a compound represented by Formula 1 between the cathode and the emission layer, and a second organic material layer represented by Formula 2 between the cathode and the first organic material layer. Except that, it can be manufactured by materials and methods known in the art. For example, the organic light emitting device of the present specification may be manufactured by sequentially laminating an anode, an organic material layer, and a cathode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, an anode is formed by depositing a metal or a conductive metal oxide or an alloy thereof on the substrate. And, after forming an organic material layer including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer and an electron injection layer thereon, it can be prepared by depositing a material that can be used as a cathode thereon. In addition to such a method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing an anode material, an organic material layer, and a cathode material on a substrate.

The organic material layer of the organic light emitting device of the present specification may have a multilayer structure in which one or more organic material layers are stacked.

In the exemplary embodiment of the present specification, the organic light emitting device includes one or two or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer. It may contain more.

When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

As the anode material, a material having a large work function is preferred so that holes can be smoothly injected into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of a metal and an oxide such as ZnO:Al or SNO ₂ :Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.

The cathode material is generally preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multilayered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

The hole injection material is a layer that injects holes from the electrode, and the hole injection material has the ability to transport holes, so it has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and is generated in the light emitting layer. A compound that prevents the transfer of the excitons into the electron injection layer or the electron injection material and has excellent thin film formation ability is preferable. It is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.

The electron blocking layer is a layer capable of improving the life and efficiency of the device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the light emitting layer.If necessary, a known material is used to improve the light emitting layer and the hole. It may be formed in an appropriate portion between the injection layer.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission layer, and the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the emission layer, and has high mobility for holes. The material is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.

When the organic light-emitting device further includes an additional light-emitting layer other than the light-emitting layer according to the exemplary embodiment of the present specification, as the light-emitting material, holes and electrons are transported from the hole transport layer and the electron transport layer, respectively, and are combined to thereby transmit light in the visible light region. As a material that can be emitted, a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzothiazole and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The emission layer may include a host material and a dopant material. Host materials include condensed aromatic ring derivatives or heterocyclic-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives and the like, but are not limited thereto.

The fluorescent emission layer is a host material, distyrylarylene (DSA), distyrylarylene derivative, distyrylbenzene (DSB), distyrylbenzene derivative, DPVBi (4,4'-bis(2,2') -diphenyl vinyl) -1,1'-biphenyl), DPVBi derivatives, spiro-DPVBi and spiro-6P (spiro-sexyphenyl) 1 or 2 or more are selected from the group consisting of.

The fluorescent emission layer is one or two or more selected from the group consisting of styrylamine-based, perylene-based, and distyrylbiphenyl (DSBP)-based dopant materials.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or light emitting material, and injects holes of excitons generated from the light emitting layer. A compound that prevents migration to the layer and has excellent thin film formation ability is preferable. When the organic light-emitting device includes an additional electron injection layer other than the electron injection layer including the compound represented by Formula 2, specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxa Sol, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include lithium 8-hydroxyquinolinato, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer, and when the organic light emitting device includes an additional electron transport layer other than the electron transport layer containing the compound represented by Formula 2, electrons As a transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high mobility for electrons is suitable. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium and samarium, and in each case, an aluminum layer or a silver layer follows.

The hole blocking layer is a layer that prevents holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. When the organic light-emitting device includes an additional hole blocking layer other than the hole blocking layer containing the compound represented by Formula 1, specifically, an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, BCP, an aluminum complex (aluminum complex) and the like, but are not limited thereto.

The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.

In addition, the organic light emitting device according to the present specification may have a normal type in which a lower electrode is an anode and an upper electrode is a cathode, and may have an inverted type in which the lower electrode is a cathode and the upper electrode is an anode.

The structure according to the exemplary embodiment of the present specification may act on a principle similar to that applied to an organic light-emitting device in organic electronic devices including organic solar cells, organic photoreceptors, and organic transistors.

Hereinafter, examples will be described in detail in order to describe the present specification in detail. However, the embodiments according to the present specification may be modified in various forms, and the scope of the present specification is not construed as being limited to the embodiments described below. The embodiments of the present specification are provided to more completely describe the present specification to those of ordinary skill in the art.

<Synthesis of the compound of Formula 1>

A method of synthesizing the compound represented by Chemical Formula 1 according to an exemplary embodiment of the present invention will be described by taking the synthesis method of compound 3-1 as an example.

[Synthesis of Compound 3-1]

A mixture of 9H-fluoren-9-one (6.95g, 38.6mmol), 4-bromophenol (13.35g, 77.2mmol) and an excess of phosphoryl chloride (POCl ₃ ) was refluxed at 120°C. After cooling to room temperature, an excessive amount of ethanol was added and then filtered. The filtered solid was dissolved in pyridine, heated, cooled to room temperature, and filtered. Compound 3A was obtained by recrystallization from chloroform and ethyl acetate.

The compound 3A (8.96 g, 21.8 mmol) and 2,4-diphenyl-6-(3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -[1,1'-biphenyl]-3-yl)-1,3,5-triazine (11.15 g, 21.8 mmol) was completely dissolved in tetrahydrofuran (100ml) and potassium carbonate (9 g, 65.4 mmol) ) Was dissolved in 50 ml of water, and tetrakistriphenyl-phosphinopalladium (756 mg, 0.65 mmol) was added, followed by heating and stirring for 8 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed to filter the white solid. The filtered white solid was washed twice with tetrahydrofuran and ethyl acetate, respectively, to prepare the compound of Formula 3-1 (12 g, yield 77%).

In the synthesis method of compound 3-1, other compounds represented by Chemical Formula 1 may be synthesized by different reactants.

For example, when naphthalen-1-ol is used instead of 4-bromophenol in the synthesis of compound 3A, the same core as compound 3B below can be synthesized.

In addition, if the position at which the bromo group is substituted in the synthesis of compound 3A is different, the position at which the substituent group on the core is substituted can be changed.

However, the method for synthesizing the compound represented by Formula 1 is not limited to the above method, and other methods may be used.

<Synthesis of the compound of Formula 2>

A method for synthesizing the compound represented by Chemical Formula 2 according to an exemplary embodiment of the present invention will be described with an example of synthesizing compounds 1-15.

Compound 4A (10 g, 29 mmol) and 2-(9,9-dimethyl-7-phenyl-9H-fluoren-3-yl)-4,4,5,5-tetramethyl-1,3,2 -Dioxaborolein (11.5 g, 29 mmol) was completely dissolved in tetrahydrofuran (100 ml), and a solution of potassium carbonate (12 g, 87 mmol) dissolved in 50 ml of water was added. Tetrakistriphenyl-phosphinopalladium (670 mg, 0.58 mmol) was added thereto, followed by heating and stirring for 12 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed and a white solid was filtered. The filtered white solid was washed twice with tetrahydrofuran and ethyl acetate, respectively, to prepare compound 1-15 (11 g, yield 66%).

Other compounds represented by Chemical Formula 2 can be synthesized by different reactants in the synthesis method of compounds 1-15. However, the synthesis method of Formula 2 is not limited to the above method, and other methods may be used.

<Example 1-1>

A glass substrate (corning 7059 glass) coated with a thin film of ITO (indium tin oxide) having a thickness of 100 nm was placed in distilled water dissolved in a dispersant and washed with ultrasonic waves. The detergent was manufactured by Fischer Co., and the distilled water was Millipore Co. Distilled water filtered secondarily with the product filter was used. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol, followed by drying.

On the thus prepared ITO transparent electrode, hexanitrile hexaazatriphenylene (HAT-CN; hexanitrile hexaazatriphenylene) was thermally vacuum deposited to a thickness of 50 nm to form a hole injection layer. On it, compound HT1 was added to A hole transport layer was formed by vacuum evaporation. The host compound BH1 and the dopant compound BD1 were vacuum deposited on the hole transport layer at a weight ratio of 97.5:2.5 to form a light emitting layer having a thickness of 30 nm. Compound 3-1 was deposited on the emission layer to form a 5 nm-thick hole blocking layer (electron control layer), and compound 1-15 and LiQ (Lithium Quinolate) were vacuum-deposited at a weight ratio of 1:1 to a thickness of 35 nm. Electron injection and transport layer was formed. Lithium fluoride (LiF) at a thickness of 1.2 nm and aluminum at a thickness of 200 nm were sequentially deposited on the electron injection and transport layer to form a cathode. An organic light emitting device was manufactured.

Was the deposition rate was 0.03 nm / sec, the deposition rate of aluminum of the deposition rate of the organic material in the above process, 0.04 nm / sec to 0.07 nm / sec, lithium fluoride is maintained to 0.2 nm / sec, During the deposition, a vacuum 2Х10 ^- Maintaining ⁷ torr to 5Х10 ^-6 torr, an organic light emitting device was manufactured.

<Examples 1-2 to 10-6>

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compounds of Table 1 below were used instead of compounds 3-1 and 1-15 in Example 1.

<Comparative Example 1>

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the electron injection and transport layer was not formed.

<Comparative Example 2>

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the hole blocking layer was not formed.

<Comparative Example 3>

An organic light-emitting device in the same manner as in Example 1-1, except that compound 1-15 was used instead of compound 3-1 for the hole blocking layer, and compound 3-2 was used instead of compound 1-15 for the electron injection and transport layer. Was produced.

<Comparative Example 4>

An organic light emitting diode was manufactured in the same manner as in Example 1-1, except that compound 3-7 was used instead of compound 3-1 for the hole blocking layer, and compound NPD was used instead of compound 1-15 for the electron injection and transport layer. .

The driving voltage and luminous efficiency of the organic light-emitting device prepared in the above experimental example were measured at a current density of 10 mA/cm ² , and the time (LT98) to become 98% of the initial luminance at a current density of 20 mA/cm ² was measured. I did. The results are shown in Table 1 below.

Compound of hole blocking layer Compound of hole injection and transport layer Driving voltage
(V) Current efficiency
(cd/A) LT98
(h) Example 1-1 3-1 1-15 3.69 5.96 31 Example 1-2 3-2 1-15 4.01 5.11 55 Example 1-3 3-3 1-15 4.00 5.25 44 Example 1-4 3-4 1-15 3.85 5.61 40 Example 1-5 3-5 1-15 3.99 5.10 56 Example 1-6 3-6 1-15 3.97 5.15 58 Example 1-7 3-7 1-15 4.10 5.05 62 Example 1-8 3-8 1-15 4.08 5.09 61 Example 1-9 3-9 1-15 4.04 4.85 65 Example 1-10 3-10 1-15 4.01 4.99 65 Example 1-11 3-11 1-15 4.00 4.81 62 Example 1-12 3-12 1-15 4.03 4.93 67 Example 1-13 3-13 1-15 3.88 5.24 44 Example 1-14 3-14 1-15 3.85 5.19 47 Example 1-15 3-15 1-15 3.98 5.43 40 Example 1-16 3-16 1-15 3.95 5.33 52 Example 1-17 3-17 1-15 3.96 5.39 50 Example 1-18 3-18 1-15 3.75 5.61 56 Conduct on 1-19 3-19 1-15 3.80 5.54 55 Example 1-20 3-20 1-15 4.02 5.63 50 Example 1-21 3-21 1-15 3.97 5.15 48 Example 1-22 3-22 1-15 4.00 5.05 58 Example 1-23 3-23 1-15 3.98 5.16 48 Example 2-1 3-1 1-52 3.77 5.85 39 Example 2-2 3-2 1-52 4.05 5.05 58 Example 2-3 3-7 1-52 4.03 5.25 49 Example 2-4 3-16 1-52 3.96 5.53 46 Example 2-5 3-20 1-52 3.98 5.05 54 Example 2-6 3-23 1-52 3.92 5.01 55 Example 3-1 3-1 1-65 3.75 5.77 44 Example 3-2 3-2 1-65 4.09 5.08 58 Example 3-3 3-7 1-65 4.10 5.11 48 Example 3-4 3-16 1-65 3.99 5.51 47 Example 3-5 3-20 1-65 4.02 5.02 55 Example 3-6 3-23 1-65 4.03 5.01 61 Example 4-1 3-1 1-95 3.71 5.99 39 Example 4-2 3-2 1-95 4.00 5.22 52 Example 4-3 3-7 1-95 4.05 5.29 48 Example 4-4 3-16 1-95 3.89 5.58 41 Example 4-5 3-20 1-95 3.99 5.19 59 Example 4-6 3-23 1-95 3.99 5.21 63 Example 5-1 3-1 1-234 3.70 5.98 40 Example 5-2 3-2 1-234 4.01 5.44 52 Example 5-3 3-7 1-234 4.01 5.21 42 Example 5-4 3-16 1-234 3.87 5.65 44 Example 5-5 3-20 1-234 3.94 5.31 52 Example 5-6 3-23 1-234 3.98 5.52 54 Example 6-1 3-1 1-403 3.74 5.66 44 Example 6-2 3-2 1-403 4.05 5.01 57 Example 6-3 3-7 1-403 4.11 5.05 45 Example 6-4 3-16 1-403 3.94 5.48 44 Example 6-5 3-20 1-403 4.05 5.10 50 Example 6-6 3-23 1-403 4.01 4.95 59 Example 7-1 3-1 2-8 3.72 5.45 40 Example 7-2 3-2 2-8 3.88 5.05 41 Example 7-3 3-7 2-8 4.04 5.11 55 Example 7-4 3-16 2-8 4.00 5.15 52 Example 7-5 3-20 2-8 4.13 5.04 63 Example 7-6 3-23 2-8 3.90 5.30 49 Example 8-1 3-1 2-16 3.96 5.28 48 Example 8-2 3-2 2-16 3.99 5.22 50 Example 8-3 3-7 2-16 3.92 5.24 48 Example 8-4 3-16 2-16 4.01 5.31 59 Example 8-5 3-20 2-16 3.92 5.24 40 Example 8-6 3-23 2-16 4.06 5.18 56 Example 9-1 3-1 2-128 4.01 5.15 59 Example 9-2 3-2 2-128 3.69 5.17 41 Example 9-3 3-7 2-128 3.81 4.91 61 Example 9-4 3-16 2-128 4.11 4.50 65 Example 9-5 3-20 2-128 3.84 5.28 44 Example 9-6 3-23 2-128 3.87 5.31 51 Example 10-1 3-1 2-359 4.18 4.59 74 Example 10-2 3-2 2-359 3.98 5.34 50 Example 10-3 3-7 2-359 4.02 5.33 52 Example 10-4 3-16 2-359 4.03 5.20 55 Example 10-5 3-20 2-359 3.81 5.25 51 Example 10-6 3-23 2-359 3.80 5.05 60 Comparative Example 1 3-1 - 5.49 2.88 26 Comparative Example 2 - 1-15 5.29 3.01 31 Comparative Example 3 1-15 3-2 5.21 4.21 18 Comparative Example 4 3-7 NPD 6.99 1.16 7

A first organic material layer provided between the cathode and the emission layer from Table 1 and including a compound represented by the following Formula 1; And a second organic material layer provided between the cathode and the first organic material layer and including a compound represented by Formula 2 below, it can be seen that driving voltage, efficiency, and/or lifetime characteristics are improved.

101: substrate
201: anode
301: hole transport layer
401: light emitting layer
402: first light-emitting layer
403: second light-emitting layer
404: third light emitting layer
501: electron transport layer
601: cathode
701: hole blocking layer
801: hole injection layer

Claims (14)

Cathode;
An anode provided to face the cathode;
An emission layer provided between the cathode and the anode;
A first organic material layer provided between the cathode and the emission layer and including a compound represented by the following formula (1); And
A second organic material layer provided between the cathode and the first organic material layer and including a compound represented by Formula 2 below,
The first organic material layer is a hole blocking layer, and the second organic material layer is an electron transport layer, an electron injection layer, or an electron injection and transport layer.
[Formula 1]

In Formula 1,
X is O or S,
At least one of R1 to R16 is a group represented by the following formula (A), and the others are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or combined with an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring,
[Formula A]

In the formula A,
At least one of X1 to X3 is N, the rest are CR,
R is hydrogen or a substituted or unsubstituted aromatic hydrocarbon ring combined with -(L2) _l2 -Ar2 or -(L3) _l3 -Ar3; Or to form a substituted or unsubstituted heterocycle,
L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
Ar2 and Ar3 are the same as or different from each other, and each independently a cyano group; A substituted or unsubstituted aryl group; A substituted or unsubstituted silyl group; Or a substituted or unsubstituted heterocyclic group,
l1 to l3 are each independently an integer of 1 to 3,
When l1 is 2 or more, two or more L1s are the same as or different from each other,
When l2 is 2 or more, 2 or more L2s are the same as or different from each other,
When l3 is 2 or more, 2 or more L3s are the same as or different from each other,

Means a moiety bonded to Formula 1,
[Formula 2]

In Formula 2,
L11 to L13 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,
Ar11 to Ar13 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group. The organic light-emitting device of claim 1, wherein the hole blocking layer is provided in contact with the emission layer. The organic light-emitting device of claim 1, wherein Formula 1 is represented by Formula 1-1 or 1-2:
[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2,
The definitions of L1 to L3, l1 to l3, Ar3, Ar2 and X1 to X3 are the same as defined in Formula A,
At least one of X4 to X6 is N, and the rest are CR',
R'is hydrogen, or a substituted or unsubstituted aromatic hydrocarbon ring combined with -(L5) _l5 -Ar4 or -(L6) _l6 -Ar5; Or to form a substituted or unsubstituted heterocycle,
L4 to L6 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
Ar4 and Ar5 are the same as or different from each other, and each independently a cyano group; A substituted or unsubstituted aryl group; A substituted or unsubstituted silyl group; Or a substituted or unsubstituted heterocyclic group,
l4 to l6 are each independently an integer of 1 to 3,
When l4 is 2 or more, 2 or more L4s are the same as or different from each other,
When l5 is 2 or more, 2 or more L5s are the same as or different from each other,
When l6 is 2 or more, 2 or more L6 are the same as or different from each other,
n1 is an integer from 0 to 2,
n2 is an integer from 0 to 2,
1 ≤ n1+n2 ≤ 4,
R100 and R101 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or combined with an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring,
r100 and r101 are each independently an integer of 1 to 8,
1≦r100+n1≦8,
1≦r101+n2≦8,
When r100 and r101 are each 2 or more, the structures in the two or more parentheses are the same as or different from each other. The organic light-emitting device of claim 1, wherein the compound represented by Formula 1 is selected from the following compounds:

. The organic light-emitting device of claim 1, wherein the substituents -L11-Ar11, -L12-Ar12, and -L13-Ar13 of Formula 2 are selected from the following structures:

. The organic light-emitting device of claim 1, wherein the emission layer includes a host and a dopant, and a maximum emission wavelength of the dopant is in a range of 420 nm to 520 nm. The organic light emitting device of claim 6, wherein the host comprises a compound represented by the following Formula 3-1:
[Formula 3-1]

In Formula 3-1,
L31 and L32 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
Ar31 and Ar32 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
R200 is hydrogen; Or a substituted or unsubstituted aryl group,
r200 is an integer from 1 to 8,
When r200 is 2 or more, two or more R200s are the same as or different from each other. The organic light-emitting device of claim 6, wherein the host is at least one selected from the following compounds:

. The organic light-emitting device of claim 1, wherein the organic light-emitting device includes two or more light-emitting layers. The organic light-emitting device of claim 9, wherein the maximum emission wavelengths of at least two of the two or more emission layers are different from each other. The method of claim 9, wherein at least one of the two or more light emitting layers comprises a phosphorescent dopant,
At least one organic light emitting device comprising a fluorescent dopant. The method according to claim 1, wherein the organic light emitting device comprises a first light emitting layer provided between the anode and the first organic material layer; And
An organic light-emitting device comprising a second emission layer provided on the first emission layer. The method according to claim 1, wherein the organic light-emitting device comprises: a first light-emitting layer provided in a portion between the anode and the first organic material layer; And
An organic light-emitting device comprising a second light-emitting layer provided on the remaining part between the anode and the first organic material layer. The method according to claim 1, wherein the organic light emitting device comprises a first light emitting layer provided between the anode and the first organic material layer; And
Including a second emission layer provided on the first emission layer,
An organic light-emitting device comprising a third emission layer provided on the second emission layer.

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