KR20210152727A - Anthracene compound, coating composition and organic light emitting device comprising same - Google Patents

Abstract

The present specification relates to an anthracene-based compound represented by chemical formula 1, and a composition and an organic light emitting device comprising the same. A compound according to an exemplary embodiment of the present specification can be used in the organic light emitting device to lower the driving voltage and improve light efficiency of the organic light emitting device.

Description

Anthracene-based compound, coating composition and organic light-emitting device comprising the same

The present specification relates to an anthracene-based compound, a coating composition comprising the same, and an organic light emitting device.

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic material layer is often formed of a multi-layered structure composed 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 the organic light emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons It lights up when it falls back to the ground state.

The development of new materials for the organic light emitting device as described above is continuously required.

KR 10-1538534 B1

An object of the present specification is to provide an anthracene-based compound, a composition including the same, and an organic light emitting device.

The present specification provides an anthracene-based compound represented by the following formula (1).

[Formula 1]

In Formula 1,

L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,

Ar1 is a halogen group; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Ar2 is a substituted or unsubstituted aryl group,

R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

D is deuterium,

n1 is an integer from 0 to 8,

m1 is an integer from 1 to 4,

r1 is an integer from 0 to 4, r2 is an integer from 0 to 2, r3 is an integer from 0 to 3,

m1 + r3 is an integer from 1 to 4, r1 + r2 is an integer from 0 to 5;

When m1, r1 and r3 are each 2 or more, the substituents in parentheses are the same as or different from each other,

When r2 is 2, R2 are the same as or different from each other.

In addition, the present specification provides a coating composition comprising the anthracene-based compound represented by the formula (1). At this time, the coating composition can be used for solution processing,

In addition, the present specification is a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one organic material layer includes the above-described anthracene-based compound.

The compound according to an exemplary embodiment of the present specification may be used in an organic light emitting device, thereby lowering the driving voltage of the organic light emitting device and improving light efficiency. In addition, the lifespan characteristics of the device can be improved by the thermal stability of the compound.

The compound or composition according to an exemplary embodiment of the present specification can be solution-processed, and a large area of the device is possible.

1 to 3 illustrate examples of an organic light emitting diode according to an exemplary embodiment of the present specification.

Hereinafter, the present specification will be described in more detail.

The anthracene-based compound represented by Formula 1 includes at least one substituent of Ar1 at the end of the 5-ring heterocyclic group, so that when used as a host for the light emitting layer of an organic light emitting device, the effect of low voltage, high efficiency and/or long life of the device is reduced. have.

When Formula 1 includes at least one deuterium, the efficiency and lifespan of the device are improved. When hydrogen is replaced with deuterium, the vibration damping effect of the molecule appears due to an increase in the weight of deuterium, which is an oscillator. This leads to a change in vibrational energy that contributes to the energy of the molecule, lowering the energy of the molecule and stabilizing it. The effect of increasing the activation energy required to break the bond of the stabilized molecule appears. Accordingly, by including deuterium in Formula 1, the efficiency and lifespan of the device may be improved.

The compound of Formula 1 containing deuterium may be prepared by a known deuterium reaction. According to an exemplary embodiment of the present specification, the compound represented by Formula 1 is formed using a deuterated compound as a precursor, or deuterium is introduced into the compound through a hydrogen-deuterium exchange reaction under an acid catalyst using a deuterated solvent. You may.

또는 점선은 연결되는 부위를 의미한다.In this specification,

Alternatively, the dotted line refers to a region to be connected.

In the present specification, Cn means that the number of carbon atoms is n, and Cn-Cm means that the number of carbons is n to m.

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

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

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; nitrile group; an alkyl group; aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a heteroaryl group containing one or more heteroatoms other than carbon, or is substituted with a substituent to which two or more substituents of the above-exemplified substituents are linked, or does not have any substituents means that

또는

의 치환기가 될 수 있다. In the present specification, that two or more substituents are connected means that the hydrogen of any one substituent is connected with the other substituent. For example, an isopropyl group and a phenyl group are linked

or

It can be a substituent of

또는

의 치환기가 될 수 있다. 4 이상의 치환기가 연결되는 것에도 전술한 것과 동일하게 적용된다.In the present specification, three substituents are connected to (substituent 1)-(substituent 2)-(substituent 3) as well as consecutively connected (substituent 1) to (substituent 2) and (substituent 3) It also includes connecting. For example, two phenyl groups and an isopropyl group are linked

or

It can be a substituent of The same applies to those in which 4 or more substituents are connected.

In the present specification, N% deuterated means that N% of hydrogen available in the structure is substituted with deuterium. For example, if 25% of dibenzofuran is substituted with deuterium, it means that 2 out of 8 hydrogens of dibenzofuran are substituted with deuterium.

In the present specification, the degree of deuteration can be confirmed by a known method such as ^{nuclear magnetic resonance spectroscopy ( 1 H NMR) or GC/MS.}

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 straight chain or branched chain, and the number of carbon atoms is not particularly limited, but 1 to 30; 1 to 20; 1 to 10; Or 1 to 5 are preferable. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, iso Pentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentyl Methyl, cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1 -Dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Cycloalkyl groups include not only monocyclic groups but also bicyclic groups such as bridgeheads, fused rings, and spiros. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, and the like, but is not limited thereto.

In the present specification, the aryl group means a monovalent group of a monovalent aromatic hydrocarbon or an aromatic hydrocarbon derivative. The aromatic hydrocarbon refers to a compound including a ring in which pi electrons are completely conjugated and a planar ring, and the group derived from an aromatic hydrocarbon refers to a structure in which an aromatic hydrocarbon or a cyclic aliphatic hydrocarbon is condensed with an aromatic hydrocarbon. Also, in the present specification, the aryl group is intended to include a monovalent group in which two or more aromatic hydrocarbons or derivatives of aromatic hydrocarbons are connected to each other. The aryl group is not particularly limited, but has 6 to 50 carbon atoms; 6 to 30; 6 to 25; 6 to 20; 6 to 18; Or it is preferably 6 to 13, and the aryl group may be monocyclic or polycyclic. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, and the like, but is not limited thereto. The polycyclic aryl group may include, but is not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a triphenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may combine with each other to form a ring.

In the present specification, when it is said that the fluorenyl group may be substituted, the substituted fluorenyl group includes all compounds in which the substituents of the pentacyclic ring of fluorene are spiro-bonded with each other to form an aromatic hydrocarbon ring. The substituted fluorenyl group includes 9,9'-spirobifluorene, spiro[cyclopentane-1,9'-fluorene], spiro[benzo[c]fluorene-7,9-fluorene], etc. However, the present invention is not limited thereto.

In the present specification, the substituted aryl group may include a form in which an aliphatic ring is condensed to an aryl group. For example, a tetrahydronaphthalene group having the following structure can be exemplified. In the following structure, one of the carbons of the benzene ring may be connected to another position.

In the present specification, the heteroaryl group refers to a monovalent aromatic heterocyclic ring. Here, the aromatic heterocycle is a monovalent group of an aromatic ring or a derivative of an aromatic ring, and means a group including at least one of N, O and S as heteroatoms in the ring. The aromatic ring derivative includes all structures in which an aromatic ring or an aliphatic ring is condensed on an aromatic ring. In addition, in the present specification, the heteroaryl group is intended to include a monovalent group in which an aromatic ring containing two or more heteroatoms or a derivative of an aromatic ring containing heteroatoms is connected to each other. the heteroaryl group having 2 to 50 carbon atoms; 2 to 30; 2 to 20; 2 to 18; Or it is preferable that it is 2-13. Examples of the heteroaryl group include a thiophene group, a furanyl group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, a pyridine group, a pyrimidine group, a triazine group, a triazole group, an acridine group, a pyridazine group, a pyrazine group, Quinoline group, quinazoline group, quinoxaline group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzo There are a furan group, a phenanthrolinyl group, a dibenzofuran group, and the like, but is not limited thereto.

In the present specification, the heteroaryl group may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic.

In the present specification, the aromatic hydrocarbon ring refers to a hydrocarbon ring in which pi electrons are completely conjugated and planar, and the description of the aryl group described above may be applied, except that it is a divalent group.

In the present specification, the aliphatic hydrocarbon ring refers to all hydrocarbon rings except for the aromatic hydrocarbon ring, and may include a cycloalkyl ring and a cycloalkene ring. Except that the cycloalkyl ring is a divalent group, the description of the cycloalkyl group described above may be applied, and the description of the cycloalkenyl group described above may be applied, except that the cycloalkenyl ring is a divalent group. The substituted aliphatic hydrocarbon ring also includes an aliphatic hydrocarbon ring in which an aromatic ring is condensed.

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

Hereinafter, the anthracene-based compound represented by the following Chemical Formula 1 will be described in detail.

[Formula 1]

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted arylene group.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted C6-C30 arylene group.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted C6-C20 arylene group.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthylene group; or a substituted or unsubstituted divalent phenanthrenyl group.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; or a C6-C30 arylene group unsubstituted or substituted with deuterium.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; or a C6-C20 arylene group unsubstituted or substituted with deuterium.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; a phenylene group unsubstituted or substituted with deuterium; a biphenylene group unsubstituted or substituted with deuterium; a naphthylene group unsubstituted or substituted with deuterium; or a divalent phenanthrenyl group unsubstituted or substituted with deuterium.

In one embodiment of the present specification, L1 is a direct bond; or a substituted or unsubstituted phenylene group.

In one embodiment of the present specification, L2 is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted naphthylene group; or a substituted or unsubstituted divalent phenanthrenyl group.

In one embodiment of the present specification, one of L1 and L2 is a direct bond.

In the exemplary embodiment of the present specification, L1 and L2 may be substituted with deuterium.

In an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently is any one selected from a direct bond or the following structure.

In the above structure, D denotes deuterium, k1 is an integer of 0 to 4, and k2 is an integer of 0 to 6.

In one embodiment of the present specification, k1 is 1 or more. In another exemplary embodiment, k1 is 2 or more. In another exemplary embodiment, k1 is 3 or more. In another exemplary embodiment, k1 is 4.

In one embodiment of the present specification, k2 is 1 or more. In another exemplary embodiment, k2 is 2 or more. In another exemplary embodiment, k2 is 3 or more. In another exemplary embodiment, k2 is 4 or more. In another exemplary embodiment, k2 is 5 or more. In another exemplary embodiment, k2 is 6.

In an exemplary embodiment of the present specification, Ar1 is a halogen group; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In an exemplary embodiment of the present specification, Ar1 is a halogen group; cyano group; a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted C3-C60 cycloalkyl group; a substituted or unsubstituted C6-C60 aryl group; Or a substituted or unsubstituted C2-C60 heteroaryl group.

In an exemplary embodiment of the present specification, Ar1 is a cyano group; a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C3-C60 cycloalkyl group; or a substituted or unsubstituted C6-C60 aryl group.

In an exemplary embodiment of the present specification, Ar1 is a halogen group; cyano group; C1-C10 alkyl group; silyl group; C3-C30 cycloalkyl group; C6-C30 aryl group; and a substituent selected from the group consisting of a C2-C30 heteroaryl group, or a substituent to which two or more groups selected from the group are connected, and Ar1 may be substituted with deuterium.

In an exemplary embodiment of the present specification, Ar1 is a halogen group; cyano group; C1-C6 alkyl group; silyl group; C3-C20 cycloalkyl group; C6-C20 aryl group; and a substituent selected from the group consisting of a C2-C20 heteroaryl group, or a substituent to which two or more groups selected from the group are connected, and Ar1 may be substituted with deuterium.

In an exemplary embodiment of the present specification, Ar1 is a fluoro group; cyano group; methyl group; ethyl group; Profile group; butyl group; pentyl group; hexyl group; silyl group; cyclopentyl group; cyclohexyl group; adamantyl group; phenyl group; biphenyl group; terphenyl group; naphthyl group; phenanthrenyl group; triphenylene group; tetrahydronatralene group; furan group; benzofuran group; dibenzofuran group; thiophene group; benzothiophene group; and a substituent selected from the group consisting of a dibenzothiophene group, or a substituent to which two or more groups selected from the group are connected, and Ar1 may be substituted with deuterium.

In an exemplary embodiment of the present specification, Ar1 is a cyano group; a C1-C10 alkyl group unsubstituted or substituted with deuterium or a halogen group; a silyl group unsubstituted or substituted with a C1-C10 alkyl group; a C3-C30 cycloalkyl group unsubstituted or substituted with deuterium; At least one substituent selected from the group consisting of deuterium, a cyano group, and a C1-C10 alkyl group, or unsubstituted or substituted with a substituent to which two or more groups selected from the group are connected, C3-C30 aliphatic hydrocarbon ring is condensed or non-condensed C6- C30 aryl group; or deuterium. It is a C2-C30 heteroaryl group unsubstituted or substituted with one or more substituents selected from the group consisting of a C1-C10 alkyl group and a C6-C30 aryl group, or a substituent to which two or more groups selected from the group are connected.

In an exemplary embodiment of the present specification, Ar1 is a cyano group; a C1-C6 alkyl group unsubstituted or substituted with deuterium or a halogen group; a silyl group unsubstituted or substituted with a C1-C6 alkyl group; a C3-C20 cycloalkyl group unsubstituted or substituted with deuterium; a C6-C20 aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a cyano group and a C1-C6 alkyl group or a substituent to which two or more groups selected from the group are connected; a C6-C40 polycyclic hydrocarbon ring in which one or more substituents selected from the group consisting of deuterium and a C1-C6 alkyl group, or two or more groups selected from the group are connected, are substituted or unsubstituted, and aromatic and aliphatic rings are condensed; or deuterium. It is a C2-C20 heteroaryl group unsubstituted or substituted with one or more substituents selected from the group consisting of a C1-C6 alkyl group and a C6-C20 aryl group, or a substituent to which two or more groups selected from the group are connected.

In the exemplary embodiment of the present specification, the heteroaryl group of Ar1 includes O or S as a heterogeneous element.

In an exemplary embodiment of the present specification, Ar1 may be substituted with deuterium.

In an exemplary embodiment of the present specification, Ar1 is a cyano group; a methyl group unsubstituted or substituted with a fluoro group; ethyl group; Profile group; butyl group; hexyl group; trimethylsilyl group; cyclopentyl group; cyclohexyl group; adamantyl group; a phenyl group unsubstituted or substituted with deuterium, a cyano group, a methyl group, or a tert-butyl group; a biphenyl group unsubstituted or substituted with deuterium; terphenyl group; a naphthyl group unsubstituted or substituted with deuterium substituted or unsubstituted with deuterium; phenanthrenyl group; tetrahydronaphthalene group unsubstituted or substituted with a methyl group; a furan group unsubstituted or substituted with a tert-butyl group; benzofuran group; a thiophene group unsubstituted or substituted with a phenyl group; or a benzothiophene group.

In an exemplary embodiment of the present specification, Ar1 is a methyl group; ethyl group; Profile group; butyl group; hexyl group; cyclopentyl group; cyclohexyl group; adamantyl group; a phenyl group unsubstituted or substituted with deuterium, a cyano group, a methyl group, or a tert-butyl group; biphenyl group; terphenyl group; a naphthyl group unsubstituted or substituted with deuterium; phenanthrenyl group; tetrahydronaphthalene group unsubstituted or substituted with a methyl group; a furan group unsubstituted or substituted with a tert-butyl group; benzofuran group; thiophene group; or a benzothiophene group.

In an exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted C6-C30 aryl group.

In an exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted C6-C20 aryl group.

In an exemplary embodiment of the present specification, Ar2 is a C6-C30 aryl group, Ar2 is one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, a C1-C10 alkyl group, and a silyl group, or selected from the group It may be substituted with a substituent to which two or more groups are connected.

In an exemplary embodiment of the present specification, Ar2 is a C6-C20 aryl group, Ar2 is one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, a C1-C6 alkyl group and a silyl group, or 2 selected from the group More than one group may be substituted with a linked substituent.

In an exemplary embodiment of the present specification, Ar2 is a C6-C20 aryl group, Ar2 is one or more substituents selected from the group consisting of deuterium, a fluoro group, a cyano group, a methyl group, a tert-butyl group, and a trimethylsilyl group, or the group Two or more groups selected from may be substituted with a connected substituent.

In an exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; Or a substituted or unsubstituted triphenylene group.

In an exemplary embodiment of the present specification, Ar2 may be substituted with deuterium.

In an exemplary embodiment of the present specification, Ar2 is a phenyl group unsubstituted or substituted with deuterium, a fluoro group, a cyano group, a methyl group, a tert-butyl group, or a trimethylsilyl group; a biphenyl group unsubstituted or substituted with deuterium; terphenyl group unsubstituted or substituted with deuterium; a naphthyl group unsubstituted or substituted with deuterium or a phenyl group; a phenanthrenyl group unsubstituted or substituted with deuterium; Or a triphenylene group unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, Ar2 is a C6-C20 aryl group unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted phenyl group unsubstituted or substituted with deuterium; a biphenyl group unsubstituted or substituted with deuterium; terphenyl group unsubstituted or substituted with deuterium; a naphthyl group unsubstituted or substituted with deuterium or a phenyl group; a phenanthrenyl group unsubstituted or substituted with deuterium; Or a triphenylene group unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C1-C20 alkyl group; or a substituted or unsubstituted C6-C60 aryl group.

In an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C1-C10 alkyl group; or a substituted or unsubstituted C6-C30 aryl group.

In an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a C1-C6 alkyl group unsubstituted or substituted with deuterium; or a C6-C20 aryl group unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; C1-C6 alkyl group; or a C6-C20 aryl group.

In an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a phenyl group.

In an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; or a phenyl group.

In an exemplary embodiment of the present specification, R1 to R3 are the same as or different from each other, and each independently hydrogen; or deuterium.

In one embodiment of the present specification, n1 is an integer from 0 to 8.

In one embodiment of the present specification, n1 is 1 or more. In another exemplary embodiment, n1 is 2 or more. In another exemplary embodiment, n1 is 3 or more. In another exemplary embodiment, n1 is 4 or more. In another exemplary embodiment, n1 is 5 or more. In another exemplary embodiment, n1 is 6 or more. In another exemplary embodiment, n1 is 7 or more. In another exemplary embodiment, n1 is 8.

In one embodiment of the present specification, m1 is an integer of 1 to 4.

In one embodiment of the present specification, m1 is 1 or 2.

When m1 is 2 or more, a plurality of Ar1s are the same as or different from each other.

In an exemplary embodiment of the present specification, r1 is an integer of 0 to 4.

In one embodiment of the present specification, r2 is an integer of 0 to 2.

In one embodiment of the present specification, r3 is an integer of 0 to 3.

When r1 is 2 or more, a plurality of R1s are the same as or different from each other.

When r2 is 2, two R2s are the same as or different from each other.

When r3 is 2 or more, a plurality of R3 are the same as or different from each other.

In one embodiment of the present specification, m1 + r3 is an integer of 1 to 4.

In one embodiment of the present specification, r1 + r2 is an integer of 0 to 5.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; or a C6-C30 arylene group unsubstituted or substituted with deuterium.

Ar1 is a halogen group; cyano group; C1-C10 alkyl group; silyl group; C3-C30 cycloalkyl group; C6-C30 aryl group; And a substituent selected from the group consisting of a C2-C30 heteroaryl group, or a substituent to which two or more groups selected from the group are connected, Ar1 may be substituted with deuterium,

Ar2 is a C6-C30 aryl group, Ar2 is one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, a C1-C10 alkyl group, and a silyl group, or two or more groups selected from the group may be substituted with a connected substituent. have.

In an exemplary embodiment of the present specification, Formula 1 is deuterated by 20% or more. In another exemplary embodiment, Formula 1 is deuterated by 30% or more. In another exemplary embodiment, Chemical Formula 1 is deuterated by 40% or more. In another exemplary embodiment, Formula 1 is deuterated by 50% or more. In another exemplary embodiment, Chemical Formula 1 is deuterated by 60% or more. In another exemplary embodiment, Chemical Formula 1 is deuterated by 70% or more. In another exemplary embodiment, Chemical Formula 1 is 80% or more deuterated. In another exemplary embodiment, Chemical Formula 1 is deuterated by 90% or more. In another exemplary embodiment, Chemical Formula 1 is 100% deuterated.

In the exemplary embodiment of the present specification, Chemical Formula 1 includes at least one hydrogen.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 101 or 102.

[Formula 101]

[Formula 102]

In Formulas 101 and 102,

L1, L2, Ar1, Ar2, R1 to R3, D, n1, m1, and r1 to r3 are the same as defined in Formula 1,

r1' is an integer from 0 to 3, and r2' is 0 or 1.

는 하기 구조에서 선택된 어느 하나이다.In one embodiment of the present specification,

is any one selected from the following structures.

In the exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of Chemical Formulas 201 to 206 below.

[Formula 201]

[Formula 202]

[Formula 203]

[Formula 204]

[Formula 205]

[Formula 206]

In Formulas 201 to 206,

L1, L2, Ar1, Ar2, R1 to R3, D, n1, m1, and r1 to r3 are the same as defined in Formula 1.

In the exemplary embodiment of the present specification, Chemical Formula 101 is one selected from the following Chemical Formulas 301 to 304.

[Formula 301] [Formula 302]

[Formula 303] [Formula 304]

In the formulas 301 to 304,

The definitions of L1, L2, Ar1, Ar2, R1 to R3, D, n1, m1, r1', r2 and r3 are as defined in Formula 101.

In the exemplary embodiment of the present specification, Chemical Formula 102 is represented by any one of Chemical Formulas 305 to 308 below.

[Formula 305] [Formula 306]

[Formula 307] [Formula 308]

In the formulas 305 to 308,

L1, L2, Ar1, Ar2, R1 to R3, D, n1, m1, r1, r2' and r3 are the same as defined in Formula 102.

는 하기 구조에서 선택된 어느 하나이다.In one embodiment of the present specification,

is any one selected from the following structures.

In the structure,

Any one of a* to f* is a position connected to L1,

R11 is hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

Ar1 is a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

m1 is an integer from 1 to 4,

r11 is an integer of 0 to 8, and when r11 is 2 or more, a plurality of R11s are the same as or different from each other.

In the exemplary embodiment of the present specification, R11 is the same as the definitions of R1 and R2 described above.

In one embodiment of the present specification, a* is a position connected to L1. In another exemplary embodiment, b* is a position connected to L1. In another exemplary embodiment, c* is a position connected to L1. In another exemplary embodiment, d* is a position connected to L1. In another exemplary embodiment, e* is a position connected to L1. In another exemplary embodiment, f* is a position connected to L1.

In an exemplary embodiment of the present specification, the anthracene-based compound represented by Formula 1 is any one selected from the following compounds.

The compound according to an exemplary embodiment of the present specification may be prepared by a method described below. If necessary, a substituent may be added or excluded, and the position of the substituent may be changed. In addition, based on techniques known in the art, starting materials, reactants, reaction conditions, etc. can be changed.

For example, the compound represented by Formula 1 may be more specific in Preparation Examples to be described later, and the reaction sequence may change depending on the compound, and the method for synthesizing the anthracene-based compound of Formula 1 is not limited to the above method.

The present specification provides a coating composition comprising the anthracene-based compound represented by Formula 1 above. At this time, the coating composition is used in the solution process in the manufacture of the organic light emitting device.

In one embodiment of the present specification, the coating composition further comprises a dopant material. As the dopant material, a dopant material to be described later may be used.

The present specification provides a composition comprising the anthracene-based compound represented by Formula 1 above. The composition may further include an additional anthracene-based compound. The additionally included anthracene-based compound is not limited to the compound represented by Formula 1, and may be a known anthracene-based host material.

The present specification provides an organic light emitting device including the above-described compound.

The present specification includes a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the anthracene-based compound represented by Formula 1 above. provides

In the present specification, when a member is said to be located “on” another member, this includes not only a case in which a member is in contact with another member but also a case in which another member is present 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 otherwise stated.

In the present specification, the "layer" is a meaning compatible with a 'film' mainly used in the art, and refers to a coating covering a desired area. The size of the “layers” is not limited, and each “layer” may have the same size or different sizes. In one embodiment, the size of a “layer” may be equal to the size of the entire device, may correspond to the size of a specific functional area, and may be as small as a single sub-pixel.

In the present specification, the meaning that a specific material A is included in layer B means that i) one or more types of material A are included in one layer B, and ii) layer B is composed of one or more layers, and material A is multi-layered B. It includes everything included in one or more floors among the floors.

In the present specification, the meaning that a specific material A is included in the C layer or the D layer means i) is included in one or more of the one or more layers C, ii) is included in one or more of the one or more layers of the D layer, or iii ) means all of which are included in one or more layers C and one or more layers D, respectively.

The organic light emitting device according to the present specification may include an additional organic material layer in addition to the light emitting layer.

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, and the like. However, the structure of the organic light emitting diode is not limited thereto.

In an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes an anthracene-based compound represented by Formula 1 above.

In an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the anthracene-based compound represented by Formula 1 as a host.

In an exemplary embodiment of the present specification, the light emitting layer includes a host and a dopant. In one embodiment, the host includes an anthracene-based compound represented by Formula 1 above.

In the exemplary embodiment of the present specification, the dopant is a phosphorescent dopant or a fluorescent dopant.

In an exemplary embodiment of the present specification, the light emitting layer includes an arylamine-based compound as a dopant.

In an exemplary embodiment of the present specification, the arylamine-based compound includes deuterium.

In another exemplary embodiment, the light emitting layer includes a boron compound as a dopant.

In an exemplary embodiment of the present specification, the dopant in the light emitting layer may be included in an amount of 0.1 to 50 parts by weight, preferably 1 to 30 parts by weight, based on 100 parts by weight of the host. When within the above range, energy transfer from the host to the dopant occurs efficiently.

In an exemplary embodiment of the present specification, the organic light emitting device further includes one or more light emitting layers. Each of the one or more emission layers may include the dopant described above.

According to an exemplary embodiment of the present specification, the organic light emitting device includes two or more emission layers, one layer of the two or more emission layers includes a fluorescent dopant, and the other layer includes a phosphorescent dopant.

According to an exemplary embodiment of the present invention, the maximum emission peak of the emission layer including the compound represented by Formula 1 is 400 nm to 500 nm.

In an exemplary embodiment of the present specification, an anthracene-based compound represented by Formula 1; Alternatively, the composition is included in an amount of 50 parts by weight or more and less than 100 parts by weight, more preferably 70 parts by weight or more and 99 parts by weight or less, based on 100 parts by weight of the total weight of the light emitting layer.

The organic light emitting device according to an exemplary embodiment of the present specification includes two or more emission layers, and at least one of the two or more emission layers includes the anthracene-based compound represented by Formula 1 above. The light emitting layer including the anthracene-based compound represented by Formula 1 may have a blue color, and the emission layer not including the anthracene-based compound represented by Formula 1 may include a blue, red, or green light-emitting compound known in the art.

In one embodiment of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, an electron blocking layer, an electron injection layer, an electron transport layer or a hole blocking layer, and the hole injection layer, the hole transport layer, the electron blocking layer, the electron The injection layer, the electron transport layer, or the hole blocking layer includes the anthracene-based compound represented by Formula 1 above.

In one embodiment of the present specification, the organic material layer is a hole injection layer, a hole transport layer. It further includes one or more layers selected from the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.

In the exemplary embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.

In the exemplary embodiment of the present specification, the second electrode is a cathode, and the first electrode is an anode.

In the exemplary embodiment of the present specification, the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

In an exemplary embodiment of the present specification, the organic light emitting device may be an inverted type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

For example, the structure of the organic light emitting device according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 to 3 , but is not limited thereto.

1 illustrates a structure of an organic light emitting device in which an anode 102, a light emitting layer 106, and a cathode 110 are sequentially stacked on a substrate 101. As shown in FIG. The compound represented by Formula 1 is included in the light emitting layer.

2 shows an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light emitting layer 106, a hole blocking layer 107, an electron transport layer 108 on a substrate 101. , the electron injection layer 109 . The structure of the organic light emitting device in which the cathode 110 and the capping layer 111 are sequentially stacked is exemplified. The compound represented by Formula 1 is included in the light emitting layer.

3 shows an anode 102, a first hole transport layer 104a, a second hole transport layer 104b, a light emitting layer 106, an electron transport layer 108, a cathode 110 and a capping layer 111 on the substrate 101. The structure of this sequentially stacked organic light emitting device is exemplified. The compound represented by Formula 1 is included in the light emitting layer.

The organic light emitting device of the present specification may be manufactured using materials and methods known in the art, except that the organic material layer includes the compound.

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.

For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form the anode. It can be prepared by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this 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, the anthracene-based compound represented by Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

In addition to this method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate. However, the manufacturing method is not limited thereto.

As the anode material, a material having a large work function is generally preferred so that holes can be smoothly injected into the organic material layer. For example, metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO ₂ : a combination of a metal such as Sb and an oxide; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. metals or alloys thereof such as, for example, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead; LiF/Al or a _{multi-layered material such as LiO 2} /Al, but is not limited thereto.

The emission layer may include a host material and a dopant material. The host material includes a condensed aromatic ring derivative or a heterocyclic compound containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and heterocyclic-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives, but is not limited thereto.

Examples of the dopant material include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, chrysene, periplanthene, and the like, having an arylamine group. In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, and one or two or more selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group A substituent is substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but is not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.

The hole injection layer is a layer that receives holes from the electrode. It is preferable that the hole injecting material has the ability to transport holes and thus has a hole receiving effect from the anode and an excellent hole injecting effect for the light emitting layer or the light emitting material. In addition, a material excellent in the ability to prevent movement of excitons generated in the light emitting layer to the electron injection layer or the electron injection material is preferable. In addition, a material excellent in the ability to form a thin film is preferable. In addition, it is preferable that the highest occupied molecular orbital (HOMO) 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 the hole injection material, metal porphyrin (porphyrin), oligothiophene, arylamine-based organic material; hexanitrile hexaazatriphenylene-based organic substances; quinacridone-based organic substances; perylene-based organic substances; Polythiophene-based conductive polymers such as anthraquinone and polyaniline, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer, and may have a single layer or a multilayer structure of two or more layers. The hole transport material is a material capable of receiving holes from the anode or the hole injection layer and transferring them to the light emitting layer, and a material having high hole mobility is preferable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.

In one embodiment of the present specification, the hole transport layer has a multilayer structure of two or more layers. Specifically, it has a two-layer structure, and each layer contains a different material.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. The electron transport material is a material capable of well injecting electrons from the cathode and transferring them to the light emitting layer, and a material having high electron mobility is preferable. Specific examples include an 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 may be used with any desired cathode material, as used in accordance with the prior art. In particular, suitable cathode materials are conventional materials having a low work function, followed by a layer of aluminum or silver. Specifically, there are cesium, barium, calcium, ytterbium and samarium, and in each case, an aluminum layer or a silver layer is followed.

The electron injection layer is a layer that receives electrons from the electrode. It is preferable that the electron injecting material has excellent electron transport ability and has an electron receiving effect from the second electrode and an excellent electron injecting effect with respect to the light emitting layer or the light emitting material. In addition, a material that prevents excitons generated in the light emitting layer from moving to the hole injection layer and has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, anthrone, etc. derivatives thereof; metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, and 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-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. , but is not limited thereto.

The electron blocking layer is a layer capable of improving the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the emission layer. A known material can be used without limitation, and may be formed between the light emitting layer and the hole injection layer or between the light emitting layer and the layer that simultaneously injects and transports holes.

The hole blocking layer is a layer that blocks the holes from reaching the cathode, and may be generally formed under the same conditions as the electron injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, and the like, but is not limited thereto.

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

Hereinafter, in order to describe the present specification in detail, it will be described in detail with reference to Examples and Comparative Examples. However, the Examples and Comparative Examples according to the present specification may be modified in various other forms, and the scope of the present specification is not to be construed as being limited to the Examples and Comparative Examples described below. Examples and comparative examples of the present specification are provided to more completely explain the present specification to those of ordinary skill in the art.

Preparation Example 1 (Synthesis of A1 to A18)

As shown in Table 1 below, after adding SM1 (leq) and SM2 (1.05eq) to tetrahydrofuran (excess), 2M aqueous potassium carbonate solution (30 volume ratio relative to THF) was added, and tetrakistriphenyl-phosphinopalladium (2mol) %), followed by heating and stirring for 10 hours. After the reaction was terminated by lowering the temperature to room temperature, the potassium carbonate aqueous solution was removed and the layers were separated. After the solvent was removed, dimethylacetamide (DMAc, excess) and potassium carbonate (3eq) were added, stirred and heated to reflux for 5 hours. After confirming the completion of the reaction, the temperature was lowered to room temperature, water (1.5 times by volume compared to DMAc) was added, and the solid obtained by filtering was purified by column chromatography using methylene chloride and hexane to obtain A1 (yield: 58%).

In the synthesis of A1, A1 to A18 were synthesized in the same manner except that SM1 and SM2 were changed as shown in Table 1 below.

Preparation Example 2 (Synthesis of B1 to B8)

As shown in Table 2 below, SM1 (1eq) and (2-hydroxyphenyl)boronic acid (1.05eq) were added to tetrahydrofuran (excess), and then 2M potassium carbonate aqueous solution (30 volume ratio compared to THF) was added, and tetrakistriphenyl - After adding phosphinopalladium (2 mol%), the mixture was heated and stirred for 10 hours. After the reaction was terminated by lowering the temperature to room temperature, the potassium carbonate aqueous solution was removed, washed twice with water, and the layers were separated. After removal of the solvent, it was dissolved in chloroform (excess), and after temperature stabilization at 0° C., N-bromosuccinimide (NBS, 1eq) was added dropwise, the temperature was raised to room temperature, and the mixture was stirred for 3 hours. After that, a saturated aqueous solution of sodium sulfate (1.5 times compared to chloroform, volume ratio) was added dropwise, extracted, and after removal of the solvent, dimethylacetamide (DMAc, excess) and potassium carbonate (3eq) were added thereto, followed by stirring and heating to reflux for 5 hours. After confirming the completion of the reaction, the temperature was lowered to room temperature, water (1.5 times the volume ratio compared to DMAc) was added, and the filtered solid was purified by column chromatography using methylene chloride and hexane to obtain B1 (yield: 59%).

In the synthesis of B1, B1 to B8 were synthesized in the same manner except that SM1 was changed as shown in Table 2 below.

Preparation Example 3 (Synthesis of C1 to C11)

In the synthesis of A1, C1 to C11 were synthesized in the same manner except that SM1 and SM2 were changed as shown in Table 3 below.

Preparation Example 4 (Synthesis of D1 to D5)

After adding SM1 (leq) and SM2 (1.05eq) of Table 4 to tetrahydrofuran (excess), 2M aqueous potassium carbonate solution (30 volume ratio relative to THF) was added, and tetrakistriphenyl-phosphinopalladium (2 mol%) ), followed by heating and stirring for 10 hours. After the reaction was terminated by lowering the temperature to room temperature, the potassium carbonate aqueous solution was removed and the layers were separated. After confirming the completion of the reaction, the temperature was extracted to room temperature, the solvent was removed, and recrystallization was performed using ethyl acetate and hexane to obtain D1 (yield: 70%).

In the synthesis of D1, D1 to D5 were synthesized in the same manner except that SM1 and SM2 were changed as shown in Table 4 below.

Preparation Example 5 (Synthesis of E1)

SM1 (leq) shown in Table 5 below was dissolved in chloroform (excess) and the temperature was stabilized at 0° C., and then N-bromosuccinimide (NBS, 1eq) was added dropwise, the temperature was raised to room temperature, and the mixture was stirred for 3 hours. Then, a saturated aqueous solution of sodium sulfate (1.5 times compared to chloroform, volume ratio) was added dropwise, extracted, and the solvent was removed and purified by column chromatography using methylene chloride and hexane to obtain E1 (yield: 65%).

Preparation 6 (Synthesis of F1)

로 냉각하고, I₂ (1eq)를 가하고 1시간 동안 교반하고 상온으로 온도를 올린 후 물(excess)을 투입하고 추출하였다 용매 제거 후 메틸렌클로라이드와 헥산을 사용하여 컬럼크로마토그래피로 정제하여 하기 표 6과 같이 F1 (수득량 : 48%)를 얻었다.SM1 (leq) of Table 6 below was dissolved in THF (excess), the temperature was lowered to -78°C, 2.5M n-BuLi (1.5eq) was added dropwise, and the temperature was stabilized at room temperature, followed by stirring for 30 minutes. again -78

After cooling to , I ₂ (leq) was added, stirred for 1 hour, the temperature was raised to room temperature, and water (excess) was added and extracted. After removing the solvent, it was purified by column chromatography using methylene chloride and hexane and purified by column chromatography. Table 6 F1 (yield: 48%) was obtained as described above.

Preparation 7 (Synthesis of G1 to G19)

SM1 (leq) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (1.3eq) of Table 7 below was added to 1,4-dioxane (12 times <mass ratio> compared to SM1), potassium acetate (3eq) was added, and stirred and refluxed. Palladium acetate (0.02eq) and tricyclohexylphosphine (0.04eq) were stirred in 1,4-dioxane for 5 minutes, added, and 2 hours later, after confirming the completion of the reaction, cooled to room temperature. After adding ethanol and water, it was filtered, and recrystallized from ethyl acetate and hexane to obtain G1 (yield: 82%).

In the synthesis of G1, G1 to G19 were synthesized in the same manner except that SM1 was changed as shown in Table 7 below.

Preparation Example 8 (Synthesis of H1 to H4)

In the synthesis of D1, H1 to H4 were synthesized in the same manner except that SM1 and SM2 were changed as shown in Table 8 below.

Preparation 9 (Synthesis of I1 to I3)

In the synthesis of G1, I1 to I3 were synthesized in the same manner except that SM1 was changed as shown in Table 9 below.

Preparation 10 (Synthesis of Compounds 1 to 19)

After adding SM1 (leq) and SM2 (1.05eq) of Table 10 to tetrahydrofuran (excess), 2M aqueous potassium carbonate solution (30 volume ratio relative to THF) was added, and tetrakistriphenyl-phosphinopalladium (2 mol%) ), followed by heating and stirring for 10 hours. After the reaction was terminated by lowering the temperature to room temperature, the potassium carbonate aqueous solution was removed and the layers were separated. After confirming the completion of the reaction, the temperature was extracted to room temperature, the solvent was removed, and recrystallization was performed using toluene to obtain compounds 1 to 19 in Table 10 below.

Preparation Example 11 (Synthesis of Compounds 20 to 22)

The reactant (leq) of Table 11 below, Trifluoromethanesulfonic acid (cat.) was added to C ₆ D ₆ (10 to 50 times the mass ratio of the reactant) and stirred at 70° C. for 10 to 100 minutes. After completion of the reaction, D ₂ O (excess) was added and stirred for 30 minutes, followed by dropwise addition of trimethylamine (excess). The reaction solution was transferred to a separatory funnel, and extracted with water and chloroform. The extract was dried over MgSO4 and recrystallized by heating with toluene to obtain compounds 20 to 22 (deuterium substituted products of compounds 4, 12 and 19) in Table 11 below.

[Each product has a different degree of deuterium substitution depending on the reaction time, and the substitution rate is determined according to the maximum m/z (M+) value]

For the deuterium substitution for the above product, reference was made to the prior literature of KR 10-1538534 B1.

<Example 1> Preparation of OLED

A substrate on which 70/1000/70 Å of ITO/Ag/ITO was deposited as an anode was placed in distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. The detergent used was a product of Fischer Co., and the distilled water was manufactured by Millipore Co. Secondary filtered distilled water was used as a filter of the product. 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 prepared anode, HI-1 was thermally vacuum deposited to a thickness of 50 Å to form a hole injection layer, and HT1, a material for transporting holes, was vacuum-deposited thereon to a thickness of 1150 Å to form a hole transport layer. Then, using EB1 to form an electron blocking layer (150 Å), then using compound 1 synthesized in Preparation Example 10 as a host, and using BD1 as a dopant (2 wt %) to form a light emitting layer (360 Å, vacuum deposition) formed. Thereafter, ET1 was deposited at 50 Å to form a hole blocking layer, and the compound ET2 and Liq were mixed at a ratio of 7:3 to form an electron transport layer having a thickness of 250 Å. Magnesium and lithium fluoride (LiF) with a thickness of 50 Å were sequentially formed as an electron injection layer, and then 200 Å of magnesium and silver (1:4) were formed as an anode, and then CP1 was deposited with 600 Å to complete the device. In the above process, the deposition rate of the organic material was maintained at 1 Å/sec.

<Examples 2 to 24>

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the host and dopant of the light emitting layer in Example 1 were as shown in Table 12 below.

<Comparative Examples 1 to 8>

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the host and dopant of the light emitting layer in Example 1 were as shown in Table 12 below.

^{A current of 20 mA/cm 2} was applied to the organic light-emitting devices prepared in Examples and Comparative Examples to measure voltage, efficiency, and lifetime (T95), and the results are shown in Table 12 below. At this time, T95 means the time until the initial luminance decreases to 95% at a current density of 20 mA/cm ^{2 .}

host dopant Voltage (V) Cd/A color coordinates
(x,y) life span
(T95, h) Example 1 compound 1 BD1 3.51 6.71 (0.135, 0.138) 49.0 Example 2 compound 2 BD1 3.45 6.63 (0.134, 0.137) 50.2 Example 3 compound 4 BD1 3.41 6.58 (0.135, 0.138) 55.2 Example 4 compound 6 BD1 3.34 6.82 (0.134, 0.138) 51.2 Example 5 compound 7 BD1 3.42 6.72 (0.136, 0.139) 48.9 Example 6 compound 9 BD1 3.31 6.52 (0.135, 0.138) 48.5 Example 7 compound 11 BD1 3.50 6.69 (0.133, 0.139) 49.1 Example 8 compound 12 BD1 3.56 6.78 (0.135, 0.138) 50.2 Example 9 compound 13 BD1 3.48 6.58 (0.134, 0.138) 50.1 Example 10 compound 14 BD1 3.50 6.67 (0.136, 0.139) 55.0 Example 11 compound 15 BD1 3.51 6.77 (0.136, 0.139) 53.5 Example 12 compound 17 BD1 3.42 6.72 (0.135, 0.138) 48.9 Example 13 compound 18 BD1 3.31 6.52 (0.135, 0.138) 48.5 Example 14 compound 19 BD1 3.50 6.69 (0.133, 0.139) 49.1 Example 15 compound 20 BD1 3.48 6.71 (0.134, 0.139) 51.1 Example 16 compound 21 BD1 3.43 6.56 (0.134, 0.138) 70.1 Example 17 compound 22 BD1 3.54 6.77 (0.135, 0.138) 73.0 Example 18 compound 23 BD1 3.51 6.68 (0.133, 0.139) 69.5 Example 19 compound 1 BD2 3.51 7.01 (0.135, 0.122) 40.2 Example 20 compound 7 BD2 3.53 7.13 (0.134, 0.121) 43.2 Example 21 compound 9 BD2 3.55 7.08 (0.136, 0.123) 41.5 Example 22 compound 12 BD2 3.55 7.12 (0.136, 0.120) 42.5 Example 23 compound 15 BD2 3.54 7.18 (0.133, 0.121) 44.1 Example 24 compound 17 BD2 3.42 7.11 (0.134, 0.122) 41.0 Comparative Example 1 BH1 BD1 3.61 5.11 (0.136, 0.139) 23.1 Comparative Example 2 BH2 BD1 3.59 5.08 (0.136, 0.139) 35.1 Comparative Example 3 BH3 BD1 3.68 5.23 (0.136, 0.139) 33.8 Comparative Example 4 BH4 BD1 3.60 5.10 (0.135, 0.138) 30.4 Comparative Example 5 BH5 BD1 3.65 5.66 (0.136, 0.139) 40.1 Comparative Example 6 BH6 BD1 3.70 4.14 (0.136, 0.139) 21.8 Comparative Example 7 BH7 BD1 3.61 5.30 (0.135, 0.138) 35.1 Comparative Example 8 BH8 BD1 3.81 5.08 (0.135, 0.138) 18.1

By using the compound of Formula 1 according to the present invention as a host of the blue organic electroluminescent device, the role of smooth hole injection into the light emitting layer can be controlled, and through the balance of holes and electrons of the organic light emitting device according to the chemical structure, in the present invention The device according to the above shows excellent characteristics in terms of efficiency, driving voltage, and stability.

<Example 25> Preparation of solution type OLED

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,300 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing the 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 with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it was transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

A solution of poly(3,4-ethylene dioxythiophene)-polystyrene sulfonate (PEDOT/PSS, manufactured by Bayer, Baytron P Al 4083) diluted in 70% with pure water by spin coating on the ITO transparent electrode prepared as described above After forming a film by the spin coating method at 3000 rpm for 30 seconds, it dried at 200 degreeC for 1 hour, and provided the 1st hole transport layer with a film thickness of 30 nm. Then, the HT1 solution (xylene solution, 1 wt%) was spin-coated to form a second hole transport layer and dried at 210° C. for 30 minutes under a nitrogen atmosphere to form a second hole transport layer with a thickness of 20 nm.

After cooling, the substrate was spin coated with the light emitting layer solution, and heated to remove the solvent to form the light emitting layer. At this time, the light emitting layer solution was prepared as a host (compound 3): dopant (BD11) = 10: 1, 1 wt% methylbenzoate solution.

After the substrate was masked and placed in a vacuum chamber, ET1 (300 Å) was deposited with LiQ in a ratio of 2:1, followed by thermal vacuum deposition as an electron transport layer. An organic light emitting device was manufactured by sequentially depositing lithium fluoride (LiF) with a thickness of 12 Å and aluminum with a thickness of 2,000 Å on the electron transport layer to form a cathode. The vacuum chamber was evacuated and the device was encapsulated using a glass cover, desiccant, and UV curable epoxy.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7 Å/sec, the deposition rate of aluminum was maintained at 2 Å/sec, and the vacuum degree during deposition was maintained at 1 × 10 ^-7 ~ 5 × 10 ^-8 torr did

<Examples 26 to 29>

An organic light emitting diode was manufactured in the same manner as in Example 25, except that the host and dopant of the light emitting layer in Example 25 were as shown in Table 13 below.

<Comparative Example 9>

An organic light emitting diode was manufactured in the same manner as in Example 25, except that the host and dopant of the light emitting layer in Example 25 were as shown in Table 13 below.

host dopant Voltage
(V) efficiency
(Cd/A) color coordinates
(x,y) life span
(T80, h)
(@1000nit) Example 25 compound 3 BD11 4.67 6.71 (0.135, 0.138) 11234.0 Example 26 compound 5 BD11 4.72 6.63 (0.134, 0.137) 10823.0 Example 27 compound 8 BD11 4.62 6.58 (0.135, 0.138) 12482.0 Example 28 compound 10 BD11 4.68 6.82 (0.134, 0.138) 10547.0 Example 29 compound 16 BD11 4.59 6.72 (0.136, 0.139) 11057.0 Comparative Example 9 BH11 BD11 5.67 5.12 (0.136, 0.139) 7200

Looking at Table 13, it can be seen that the compound of Formula 1 according to the present invention can be used in a solution process, and when used as a host of a blue organic electroluminescent device, it can be seen that the device has excellent characteristics of low voltage, high efficiency and long life. can

101: substrate
102: positive electrode
103: hole injection layer
104: hole transport layer
104a: first hole transport layer
104b: second hole transport layer
105: electron blocking layer
106: light emitting layer
107: hole blocking layer
108: electron transport layer
109: electron injection layer
110: cathode
111: capping layer

Claims (14)

Anthracene-based compound represented by the following formula (1):
[Formula 1]

In Formula 1,
L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,
Ar1 is a halogen group; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
Ar2 is a substituted or unsubstituted aryl group,
R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
D is deuterium,
n1 is an integer from 0 to 8,
m1 is an integer from 1 to 4,
r1 is an integer from 0 to 4, r2 is an integer from 0 to 2, r3 is an integer from 0 to 3,
m1 + r3 is an integer from 1 to 4, r1 + r2 is an integer from 0 to 5;
When m1, r1 and r3 are each 2 or more, the substituents in parentheses are the same as or different from each other,
When r2 is 2, R2 are the same as or different from each other. The anthracene-based compound according to claim 1, wherein Chemical Formula 1 is represented by the following Chemical Formula 101 or 102:
[Formula 101]

[Formula 102]

In Formulas 101 and 102,
L1, L2, Ar1, Ar2, R1 to R3, D, n1, m1, and r1 to r3 are the same as defined in Formula 1,
r1' is an integer from 0 to 3, and r2' is 0 or 1. The anthracene-based compound according to claim 1, wherein Chemical Formula 1 is represented by any one of Chemical Formulas 201 to 206:
[Formula 201]

[Formula 202]

[Formula 203]

[Formula 204]

[Formula 205]

[Formula 206]

In Formulas 201 to 206,
L1, L2, Ar1, Ar2, R1 to R3, D, n1, m1, and r1 to r3 are the same as defined in Formula 1. The method according to claim 1,
L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a C6-C30 arylene group unsubstituted or substituted with deuterium;
Ar1 is a halogen group; cyano group; C1-C10 alkyl group; silyl group; C3-C30 cycloalkyl group; C6-C30 aryl group; And a substituent selected from the group consisting of a C2-C30 heteroaryl group, or a substituent to which two or more groups selected from the group are connected, Ar1 may be substituted with deuterium,
Ar2 is a C6-C30 aryl group, Ar2 is one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, a C1-C10 alkyl group, and a silyl group, or two or more groups selected from the group may be substituted with a connected substituent. Anthracene-based compounds that exist. The method according to claim 1,
R1 to R3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a C1-C6 alkyl group unsubstituted or substituted with deuterium; Or an anthracene-based compound that is a C6-C20 aryl group unsubstituted or substituted with deuterium. The method according to claim 1, wherein Formula 1 is an anthracene-based compound that is 20% or more deuterated, The method according to claim 1, wherein Formula 1 is an anthracene-based compound comprising at least one hydrogen, The anthracene-based compound according to claim 1, wherein the anthracene-based compound represented by Formula 1 is any one selected from the following compounds:

. A coating composition comprising the anthracene-based compound according to any one of claims 1 to 8. a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode,
At least one of the organic material layers is an organic light emitting device comprising the anthracene-based compound according to any one of claims 1 to 8. The method according to claim 10, wherein the organic material layer comprises a light emitting layer, the light emitting layer is the anthracene-based compound; Or an organic light emitting device comprising the composition as a host. The organic light-emitting device of claim 11 , wherein the emission layer includes an arylamine-based compound as a dopant. The organic light-emitting device of claim 11 , wherein the emission layer includes a boron compound as a dopant. The method according to claim 10, wherein the organic material layer is a hole injection layer, a hole transport layer. The organic light emitting device further comprising one or more layers selected from the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.

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