KR20180114470A - Anthracene derivatives and organic light emitting device using the same - Google Patents

Abstract

The present invention relates to an anthracene derivative represented by chemical formula 1, a coating composition containing the anthracene derivative, an organic light emitting device using the same, and a method for manufacturing the same. In chemical formula 1, Ar1 and Ar2 are the same or different from each other and each independently hydrogen; heavy hydrogen; a silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an anthracene derivative and an organic light emitting device using the same.

The present invention relates to an anthracene derivative and an organic light emitting device using the same.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic layer between them. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected into the anode, electrons are injected into the organic layer, electrons are injected into the organic layer, excitons are formed when injected holes and electrons meet, When it falls to a state, it becomes a light. Such an organic light emitting device is known to have characteristics such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

A material used as an organic material layer in an organic light emitting device can be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions. The light emitting material can be classified into blue, green and red light emitting materials and yellow and orange light emitting materials necessary for realizing better natural color depending on the luminescent color. Further, in order to increase the color purity and increase the luminous efficiency through energy transfer, a host / dopant system can be used as a light emitting material. The principle is that a small amount of dopant having a smaller energy band gap and a higher luminous efficiency than a host mainly constituting the light emitting layer is mixed with the light emitting layer in a small amount, and the excitons generated in the host are transported to the dopant to emit highly efficient light. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, the desired wavelength light can be obtained depending on the type of the dopant used.

In order to sufficiently exhibit the excellent characteristics of the organic light emitting device, a material constituting the organic material layer in the device such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, and an electron injecting material is supported by a stable and efficient material Should be preceded.

Among them, organometallic complexes having a relatively high stability to electrons and electron transfer rates as organic monomolecular materials are preferable as electron transport materials. Among them, Alq ₃ having excellent stability and high electron affinity has been reported to be the most excellent, but when used in a blue light emitting device, there is a problem that the color purity drops due to exciton diffusion. Flavon derivatives of sanyo or germanium and silicon clopetadiene derivatives of Chisso are known (JP-A-1998-017860, JP-A-1999-087067) .

As the organic monomolecular substance, a PBD (2-biphenyl-4-yl-5- (4-t-butylphenyl) -1,3,4-oxadiazole) derivative bonded to a Spiro compound and a hole blocking ability (2,2 ', 2 "- (benzene-1,3,5-triyl) -tris (1-phenyl-1H-benzimidazole) which has both excellent electron transporting ability , 1998, 1136 & Tao et al, Appl. Phys. Lett., 77, 2000, 1575), and benzoimidazole derivatives disclosed in LG Chem are widely known for their excellent durability.

Organic light emitting devices using the organic single molecular material as an electron transporting layer have short lifetime, low storage durability and low reliability. These problems are caused by physical or chemical changes of organic materials, photochemical or electrochemical changes of organic materials, oxidation and peeling of the cathodes, and durability.

Therefore, organic light emitting devices using a method of obtaining arbitrary luminescent color by changing the structure of an organic monomolecular material used in an organic luminescent device or obtaining various high efficiencies by a host dopant system have been proposed, Characteristics, life span and durability.

For example, Korean Patent Publication No. 2003-0067773 discloses a compound having a benzoimidazole ring and an anthracene skeleton.

However, there is a continuing need for the development of new materials having improved luminescence brightness, luminescence efficiency, and lifetime, as compared with organic EL devices using such compounds.

Korean Patent Publication No. 10-2003-0067773

The present invention provides an anthracene-based compound, a coating composition containing the compound, a glass light-emitting device obtained by drying the coating composition by heat treatment or light treatment, and a method of manufacturing the organic light-emitting device.

One embodiment of the present disclosure provides compounds of formula 1:

[Chemical Formula 1]

In Formula 1,

Ar1 and Ar2 are the same or different from each other, and each independently hydrogen; heavy hydrogen; Silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

Ar3 and Ar4 are the same or different and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

a and b are each an integer of 0 to 9,

c and d are each an integer of 1 to 3,

e and f are each an integer of 1 or 2,

Wherein L1 is selected from the following structural formulas,

R1 to R4 are the same or different from each other and each independently hydrogen; heavy hydrogen; Silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or R1 and R2 or R3 and R4 may be bonded to each other to form an aliphatic ring or an aromatic ring,

R6 to R9 and R11 to R18 are the same or different from each other, and each independently hydrogen; heavy hydrogen; Silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group

R5 and R19 to R21 each independently represent a substituted or unsubstituted alkylene group; A substituted or unsubstituted cycloalkylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

R10 is a substituted or unsubstituted cycloalkylene group; Or a substituted or unsubstituted arylene group,

R22 is a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted cycloalkylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

m1 to m6 and n1 and n2 each independently represent an integer of 1 to 20,

m7 is an integer of 1 to 20,

L2 and L3 are the same or different from each other, and are each independently a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group.

Another embodiment of the present disclosure provides a coating composition comprising the compound.

Another embodiment of the present disclosure also includes a cathode; Anode; And one or more organic layers disposed between the cathode and the anode, wherein at least one of the organic layers includes a dried material or a cured product of the coating composition.

Finally, another embodiment of the present disclosure provides a method of manufacturing a semiconductor device, comprising: preparing a substrate; Forming a cathode or an anode on the substrate; Forming at least one organic material layer on the cathode or the anode; And forming an anode or a cathode on the organic material layer, wherein the forming the organic material layer includes forming one or more organic material layers using the coating composition. do.

The compound according to the present invention can be used as an organic material layer material of an organic light emitting device, and the compound can be subjected to a solution process, thereby enabling the device to have a large area. The light emitting layer of the organic light emitting device can be formed by a solution process by connecting the light emitting materials by using the material for increasing the solubility, thereby greatly improving the processability.

1 shows an example of an organic light emitting device according to an embodiment of the present invention.
2 is a MS graph of the compound of the compound 1-1 of the present invention.
Figure 3 is a MS graph of the compound of intermediate compound C of the present invention.
4 is a MS graph of the intermediate compound D of the present invention.
Figure 5 is a MS graph of the compounds 1-2 of the present invention.
6 is an MS graph of the compounds 1-3 of the present invention.

Hereinafter, the present specification will be described in detail.

In this specification, when a part is referred to as " including " an element, it is to be understood that it may include other elements as well, without departing from the other elements unless specifically stated otherwise.

An embodiment of the present invention provides a compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

Ar1 and Ar2 are the same or different from each other, and each independently hydrogen; heavy hydrogen; Silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

Ar3 and Ar4 are the same or different and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

a and b are each an integer of 0 to 9,

c and d are each an integer of 1 to 3,

e and f are each an integer of 1 or 2,

Wherein L1 is selected from the following structural formulas,

R1 to R4 are the same or different from each other and each independently hydrogen; heavy hydrogen; Silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or R1 and R2 or R3 and R4 may be bonded to each other to form an aliphatic ring or an aromatic ring,

R6 to R9 and R11 to R18 are the same or different from each other, and each independently hydrogen; heavy hydrogen; Silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group

R5 and R19 to R21 each independently represent a substituted or unsubstituted alkylene group; A substituted or unsubstituted cycloalkylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

R10 is a substituted or unsubstituted cycloalkylene group; Or a substituted or unsubstituted arylene group,

R22 is a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted cycloalkylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

m1 to m6 and n1 and n2 each independently represent an integer of 1 to 20,

m7 is an integer of 1 to 20,

L2 and L3 are the same or different from each other, and are each independently a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group.

The compound of Formula 1 according to one embodiment of the present invention has an effect of forming an organic layer by a solution process by introducing a structure capable of increasing the solubility of a compound between two anthracene structures. For example, the compound of Formula 1 has solubility in an organic solvent such as dichloromethane, toluene, chlorobenzene, cyclohexanone, etc., and the solubility may be 3 wt% or more based on the total amount of the organic solvent.

Thus, by using a compound that can be used in a solution process as an organic material layer material of an organic light emitting device, an organic light emitting device can be manufactured by a solution coating method, which is economical in terms of time and cost. Further, an organic light emitting device can be manufactured by a solution coating method, and the device can be made larger.

Particularly, the anthracene structure located on both sides of the structure capable of increasing solubility can be used as a light emitting layer material, particularly a host material, of an organic light emitting device, and is useful as a light emitting layer material applicable to a solution process Can be used.

Hereinafter, the substituent of the present specification will be described in detail.

는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.In the present specification,

Quot; refers to a moiety bonded to another substituent or bond.

In the present specification, the term " substituted " means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the substituted position is not limited as long as the substituent is a substitutable position, When two or more substituents are substituted, two or more substituents may be the same as or different from each other.

As used herein, the term " substituted or unsubstituted " heavy hydrogen; Silyl group; A halogen group; A nitrile group; A nitro group; A hydroxy group; An alkyl group; An alkoxy group; An alkenyl group; An aryl group; And a heterocyclic group, or a substituted or unsubstituted one in which at least two of the above-exemplified substituents are connected to each other. For example, the "substituent group to which at least two substituents are connected" includes a heterocyclic group substituted with an aryl group, an aryl group substituted with a heterocyclic group, or an aryl group substituted with an alkyl group.

In the present specification, the halogen group is fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group may be linear, branched or cyclic, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, 3-methylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, Cyclohexyl, cycloheptyl, cyclooctyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2- Propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl 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 is preferably 1 to 20 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is not limited thereto.

In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.

In the present specification, the silyl group may be represented by the formula of -SiRR'R ", wherein R, R 'and R" are each hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. Specific examples include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, But is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 40 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 40 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.

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

,

,

및

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

And

And the like. However, the present invention is not limited thereto.

In the present specification, the heterocyclic group includes one or more atoms other than carbon, hetero atom. The number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 40. [ According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 20. The heterocyclic group may be monocyclic or polycyclic. Examples of the heterocyclic group include a thiophene group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, , An isoquinolinyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, But are not limited to, phenanthroline, thiazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazyl and dibenzofuranyl groups.

In the present specification, the arylene group may be selected from the examples of the aryl group described above, except that it is a divalent group.

In the present specification, the alkylene group may be selected from the examples of the alkyl group described above, except that it is a divalent group.

In the present specification, the cycloalkylene group may be selected from the examples of the above-mentioned cycloalkyl group, except that it is a divalent group.

In the present specification, the bivalent heterocyclic group can be selected from the examples of the above-mentioned heterocyclic groups, except that it is a divalent group.

In one embodiment of the present invention, the formula (1) may be represented by the following formula (2).

(2)

Ar 3, Ar 4, c to f, and L 1 to L 3 in the general formula (2) are as defined in formula (1)

Ar5 to Ar8 are the same or different from each other, and each independently hydrogen; heavy hydrogen; Silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

Ar9 and Ar10 are the same or different from each other, and each independently hydrogen; heavy hydrogen; Silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

g to j are each an integer of 0 to 4;

According to one embodiment of the present disclosure, R 1 and R 2 are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may be bonded to each other to form an aliphatic ring or an aromatic ring.

According to one embodiment of the present disclosure, R 1 and R 2 are the same or different and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group or a substituted or unsubstituted aryl group, or may form a substituted or unsubstituted ring.

According to one embodiment of the present disclosure, R 1 and R 2 are the same or different and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted C6-C20 cycloalkyl group; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or may combine with each other to form an aliphatic ring or an aromatic ring.

According to one embodiment of the present disclosure, R 1 and R 2 are the same or different and each independently hydrogen; Methyl group; A substituted or unsubstituted cyclohexyl group; Or a substituted or unsubstituted phenyl group, or may be bonded to each other to form an aliphatic ring or an aromatic ring.

According to one embodiment of the present disclosure, R 1 and R 2 are the same or different and each independently hydrogen; Methyl group; A cyclohexyl group; Or a phenyl group, or may combine with each other to form an aliphatic ring or an aromatic ring.

According to one embodiment of the present disclosure, R 3 and R 4 are the same or different and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present disclosure, R 3 and R 4 are the same or different and are each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group.

According to one embodiment of the present invention, R 3 and R 4 are the same or different and are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted cycloalkyl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C6 to C20 aryl group.

According to one embodiment of the present disclosure, R3 and R4 are the same or different from each other and are each independently a methyl group; A substituted or unsubstituted cyclohexyl group; Substituted or unsubstituted or phenyl group.

According to one embodiment of the present disclosure, R3 and R4 are the same or different from each other and are each independently a methyl group; A cyclohexyl group; Or a phenyl group.

R6 to R9 and R11 to R18 are the same or different from each other, and each independently hydrogen; heavy hydrogen; Silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

According to one embodiment of the present disclosure, R6 to R9 and R11 to R18 are substituted or unsubstituted alkyl groups.

According to one embodiment of the present invention, R6 to R9 and R11 to R18 are substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms.

According to one embodiment of the present invention, R6 to R9 and R11 to R18 are alkyl groups having 1 to 10 carbon atoms.

According to one embodiment of the present disclosure, R6 to R9 and R11 to R18 are methyl groups.

According to one embodiment of the present invention, R5 is an independently substituted or unsubstituted alkylene group; A substituted or unsubstituted cycloalkylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group.

According to one embodiment of the present invention, R5 is an independently substituted or unsubstituted alkylene group; A substituted or unsubstituted cycloalkylene group; Or a substituted or unsubstituted arylene group.

According to one embodiment of the present invention, R5 is independently a substituted or unsubstituted alkylene group having 2 to 10 carbon atoms; A substituted or unsubstituted C6-C20 cycloalkylene group; Or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

According to one embodiment of the present disclosure, each R5 is independently a substituted or unsubstituted ethylene group; A substituted or unsubstituted hexylene group; A substituted or unsubstituted cyclohexylene group; Or a substituted or unsubstituted phenylene group.

According to one embodiment of the present disclosure, each R5 is independently an ethylene group; A hexylene group; Cyclohexylene group; Or a phenylene group.

According to one embodiment of the present invention, R10 is a substituted or unsubstituted C6-C20 cycloalkylene group or a substituted or unsubstituted C6-C20 arylene group.

According to one embodiment of the present specification, R10 is a substituted or unsubstituted cyclohexylene group or a substituted or unsubstituted phenylene group.

According to one embodiment of the present disclosure, R10 is a cyclohexylene group or a phenylene group.

According to one embodiment of the present specification, R19 and R20 each independently represent a substituted or unsubstituted alkylene group; A substituted or unsubstituted cycloalkylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group.

According to one embodiment of the present specification, R19 and R20 are each independently a substituted or unsubstituted alkylene group.

According to one embodiment of the present specification, R19 and R20 are each independently a substituted or unsubstituted C2-C10 alkylene group.

According to one embodiment of the present disclosure, R19 and R20 are each independently a substituted or unsubstituted ethylene group.

According to one embodiment of the present disclosure, R19 and R20 are ethylene groups.

According to one embodiment of the present disclosure, R21 is a substituted or unsubstituted arylene group.

According to one embodiment of the present disclosure, R21 is a substituted or unsubstituted fluorenyl group; Or a substituted or unsubstituted phenylene group.

According to one embodiment of the present disclosure, R21 is a fluorenyl group substituted with an alkyl group; Or a phenylene group substituted or unsubstituted with an alkyl group.

According to one embodiment of the present invention, R21 is a fluorenyl group substituted with an alkyl group having 2 to 10 carbon atoms; Or a phenylene group substituted with an alkyl group having 2 to 10 carbon atoms.

According to one embodiment of the present disclosure, R21 is a fluorenyl group substituted with an octyl group; Or an octyl group.

According to one embodiment of the present disclosure, R21 is a fluorenyl group substituted with an octyl group; Or a phenylene group.

According to one embodiment of the present disclosure, m1 to m6 are each independently an integer of 1 to 3.

According to one embodiment of the present disclosure, m1 to m4 are independently integers of 1 or 2, respectively.

According to one embodiment of the present disclosure, m3 and m4 are one.

According to one embodiment of the present disclosure, n1 and n2 are each independently an integer of 1 to 3.

According to one embodiment of the present disclosure, L2 and L3 are the same or different from each other, and are each independently a direct bond; Or a substituted or unsubstituted arylene group.

According to one embodiment of the present disclosure, L2 and L3 are the same or different from each other, and are each independently a direct bond; Or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

According to one embodiment of the present disclosure, L2 and L3 are the same or different from each other, and are each independently a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted naphthylene group.

According to one embodiment of the present disclosure, L2 and L3 are the same or different from each other, and are each independently a direct bond; A phenylene group; Or a naphthylene group.

In one embodiment of the present specification, Ar3 and Ar4 are the same or different and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, Ar3 and Ar4 are the same or different and are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 6 to 30 carbon atoms.

In one embodiment of the present specification, Ar3 and Ar4 are the same or different and are each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted divalent dibenzothiophene group; Or a substituted or unsubstituted divalent dibenzofurane group.

In one embodiment of the present specification, Ar3 and Ar4 are the same or different and are each independently a direct bond; A phenylene group substituted or unsubstituted with an alkyl group; A biphenylene group substituted or unsubstituted with an alkyl group; A naphthylene group substituted or unsubstituted with an alkyl group; A phenanthrenyl group substituted or unsubstituted with an alkyl group; Anthracenyl group substituted or unsubstituted with an alkyl group; A fluorenyl group substituted or unsubstituted with an alkyl group; A divalent dibenzothiophene group substituted or unsubstituted with an alkyl group; Or a divalent dibenzofurane group substituted or unsubstituted with an alkyl group.

In one embodiment of the present specification, Ar3 and Ar4 are the same or different and are each independently a direct bond; A phenylene group substituted or unsubstituted with an alkyl group having 6 to 8 carbon atoms; A biphenylene group substituted or unsubstituted with an alkyl group having 6 to 8 carbon atoms; A naphthylene group substituted or unsubstituted with an alkyl group having 6 to 8 carbon atoms; A phenanthrenyl group substituted or unsubstituted with an alkyl group having 6 to 8 carbon atoms; Anthracenyl group substituted or unsubstituted with an alkyl group having 6 to 8 carbon atoms; A fluorenyl group substituted or unsubstituted with an alkyl group having 6 to 8 carbon atoms; A divalent dibenzothiophene group substituted or unsubstituted with an alkyl group having 6 to 8 carbon atoms; Or a divalent dibenzofurane group substituted or unsubstituted with an alkyl group having 6 to 8 carbon atoms.

In one embodiment of the present specification, Ar3 and Ar4 are the same or different and are each independently a direct bond; A phenylene group substituted or unsubstituted with a hexyl group or an octyl group; A biphenylene group substituted or unsubstituted with a hexyl group or an octyl group; A naphthylene group substituted or unsubstituted with a hexyl group or an octyl group; A phenanthrenyl group substituted or unsubstituted with a hexyl group or an octyl group; Anthracenyl group substituted or unsubstituted with a hexyl group or an octyl group; A fluorenyl group substituted or unsubstituted with a hexyl group or an octyl group; A divalent dibenzothiophene group substituted or unsubstituted with a hexyl group or an octyl group; Or a divalent dibenzofurane group substituted or unsubstituted with a hexyl group or an octyl group.

In one embodiment of the present specification, Ar3 and Ar4 are the same or different and are each independently a direct bond; A phenylene group; Biphenylene group; Naphthylene group; A phenanthrenyl group; Anthracenyl group; A fluorenyl group substituted or unsubstituted with a hexyl group or an octyl group; A divalent dibenzothiophene group; Or a divalent dibenzofurane group.

In one embodiment of the present specification, Ar3 and Ar4 are the same or different and are each independently a direct bond; A phenylene group; Biphenylene group; Naphthylene group; A phenanthrenyl group; Anthracenyl group; A fluorenyl group; A divalent dibenzothiophene group; Or a divalent dibenzofurane group.

In one embodiment of the present specification, Ar3 and Ar4 are the same or different and are each independently a direct bond; A phenylene group; Biphenylene group; Naphthylene group; Or a divalent dibenzofurane group.

Ar5 to Ar8 are the same or different from each other, and each independently hydrogen; heavy hydrogen; Silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

Ar5 to Ar8 are the same or different from each other, and each independently hydrogen; Silyl group; Or a substituted or unsubstituted alkyl group.

Ar5 to Ar8 are the same or different from each other, and each independently hydrogen; Silyl group; Or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

Ar5 to Ar8 are the same or different from each other, and each independently hydrogen; A trimethylsilyl group; Or a substituted or unsubstituted tert-butyl group.

Ar5 to Ar8 are the same or different from each other, and each independently hydrogen; A trimethylsilyl group; Or a tert-butyl group.

In one embodiment of the present specification, Ar9 and Ar10 are the same or different and each independently hydrogen; Silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, Ar9 and Ar10 are the same or different and each independently hydrogen; Silyl group; A substituted or unsubstituted alkyl group having 2 to 10 carbon atoms; A substituted or unsubstituted C6 to C20 aryl; Or a substituted or unsubstituted heterocyclic group having 6 to 60 carbon atoms.

In one embodiment of the present specification, Ar9 and Ar10 are the same or different and each independently hydrogen; Silyl group; A substituted or unsubstituted isopropyl group; tert-butyl group; A substituted or unsubstituted hexyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthalene group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted dibenzofurane group.

In one embodiment of the present specification, Ar9 and Ar10 are the same or different and each independently hydrogen; Silyl group; An isopropyl group substituted or unsubstituted with an alkyl group; tert-butyl group; A hexyl group substituted or unsubstituted with an alkyl group; A phenyl group substituted or unsubstituted with an alkyl group; A naphthalene group substituted or unsubstituted with an alkyl group; An anthracene group substituted or unsubstituted with an alkyl group; A phenanthrene group substituted or unsubstituted with an alkyl group; A fluorene group substituted or unsubstituted with an alkyl group; A dibenzothiophene group substituted or unsubstituted with an alkyl group; Or a dibenzofurane group substituted or unsubstituted with an alkyl group.

In one embodiment of the present specification, Ar9 and Ar10 are the same or different and each independently hydrogen; Silyl group; tert-butyl group; A hexyl group substituted or unsubstituted with an alkyl group having 6 to 8 carbon atoms; A phenyl group substituted or unsubstituted with an alkyl group having 6 to 8 carbon atoms; A naphthalene group substituted or unsubstituted with an alkyl group having 6 to 8 carbon atoms; An anthracene group substituted or unsubstituted with an alkyl group having 6 to 8 carbon atoms; A phenanthrene group substituted or unsubstituted with an alkyl group having 6 to 8 carbon atoms; A fluorene group substituted or unsubstituted with an alkyl group having 6 to 8 carbon atoms; A dibenzothiophene group substituted or unsubstituted with an alkyl group having 6 to 8 carbon atoms; Or a dibenzofurane group substituted or unsubstituted with an alkyl group having 6 to 8 carbon atoms.

In one embodiment of the present specification, Ar9 and Ar10 are the same or different and each independently hydrogen; Silyl group; tert-butyl group; An isopropyl group substituted or unsubstituted with a hexyl group or an octyl group; A hexyl group substituted or unsubstituted with a hexyl group or an octyl group; A phenyl group substituted or unsubstituted with a hexyl group or an octyl group; A naphthalene group substituted or unsubstituted with a hexyl group or an octyl group; An anthracene group substituted or unsubstituted with a hexyl group or an octyl group; A phenanthrene group substituted or unsubstituted with a hexyl group or an octyl group; A fluorene group substituted or unsubstituted with a hexyl group or an octyl group; A dibenzothiophene group substituted or unsubstituted with a hexyl group or an octyl group; Or a dibenzofurane group substituted or unsubstituted with a hexyl group or an octyl group.

In one embodiment of the present specification, Ar9 and Ar10 are the same or different and each independently hydrogen; Silyl group; Isopropyl group; tert-butyl group; Hexyl group; A phenyl group; A naphthalene group; Anthracene group; Phenanthrene; A fluorene group substituted or unsubstituted with a hexyl group or an octyl group; A dibenzothiophene group; Or a dibenzofurane group.

In one embodiment of the present specification, Ar9 and Ar10 are the same or different and each independently hydrogen; Silyl group; Isopropyl group; tert-butyl group; Hexyl group; A phenyl group; A naphthalene group; Anthracene group; Phenanthrene; A fluorene group; A dibenzothiophene group; Or a dibenzofurane group.

In one embodiment of the present specification, Ar9 and Ar10 are the same or different and each independently hydrogen; Silyl group; tert-butyl group; Isopropyl group; Hexyl group; A phenyl group; Or a naphthalene group.

In one embodiment of the present specification, Ar9 and Ar10 are the same or different and each independently hydrogen; A trimethylsilyl group; tert-butyldimethylsilyl group; tert-butyldiphenylsilyl group; t-butyl group; Isopropyl group; Hexyl group; A phenyl group; Or a naphthalene group.

According to one embodiment of the present invention, the compound represented by Formula 1 may be represented by any one of the following compounds.

The compound according to one embodiment of the present specification can be produced by a production method described below.

For example, the compound of Formula 1 can be prepared by the same method as the preparation example described below. Substituent groups may be attached by methods known in the art, and the type, position or number of substituent groups may be varied according to techniques known in the art.

In one embodiment of the present disclosure, coating compositions comprising the compounds described above are provided.

In one embodiment of the present disclosure, the coating composition comprises less than 90% by weight of the compound of Formula 1 based on the total solution. For example, 0.1 wt% or more and 90 wt% or less, preferably 3 wt% or more and 90 wt% or less.

In one embodiment of the present disclosure, the viscosity of the coating composition is between 2 cP and 15 cP. When having a viscosity in the above range, it is easy to manufacture the device.

In one embodiment of the present disclosure, the coating composition may be in a liquid phase. The "liquid phase" means that the liquid phase is at normal temperature and pressure.

In one embodiment of the present invention, the solvent includes, for example, chlorinated solvents such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene and o-dichlorobenzene; Ether solvents such as tetrahydrofuran and dioxane; Aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene and mesitylene; Aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane and n-decane; Ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone, isophorone, tetralone, decalone, and acetylacetone; Ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate; Examples of polyhydric alcohols such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, Alcohols and their derivatives; Alcohol solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; Sulfoxide-based solvents such as dimethylsulfoxide; And amide solvents such as N-methyl-2-pyrrolidone and N, N-dimethylformamide; A solvent such as tetralin is exemplified, but a solvent capable of dissolving or dispersing the anthracene derivative according to one embodiment of the present invention is sufficient, and the solvent is not limited thereto.

In another embodiment, the solvents may be used alone or in combination of two or more solvents.

In one embodiment of the present disclosure, the coating composition may further comprise a luminescent dopant. Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.

In one embodiment of the present invention, the dopant may be a known dopant. For example, a dopant such as the following structure can be used.

The present disclosure also provides an organic light emitting device formed using the coating composition.

In one embodiment of the present disclosure, a cathode; Anode; And at least one organic material layer provided between the cathode and the anode, wherein at least one of the organic material layers is formed using the coating composition, thereby including the dried material of the coating composition.

In one embodiment of the present invention, the organic layer including the dried product of the coating composition is a light emitting layer.

In one embodiment of the present invention, the organic light emitting element is a hole injection layer, a hole transport layer, An electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer.

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

In another embodiment, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, at least one organic layer, and an anode are sequentially stacked on a substrate.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

For example, the structure of an organic light emitting device according to one embodiment of the present specification is illustrated in FIG.

1 shows an organic light emitting device in which an anode 201, a hole injecting layer 301, a hole transporting layer 401, a light emitting layer 501, an electron transporting layer 601 and a cathode 701 are sequentially stacked on a substrate 101 Are illustrated. Here, the light emitting layer 501 may include a dried product or a cured product of the above-described coating composition.

FIG. 1 illustrates an organic light emitting device and is not limited thereto.

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

The organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer is formed using a coating composition containing the compound of the formula (1).

For example, the organic light emitting device of the present specification can be manufactured by sequentially laminating an anode, an organic layer, and a cathode on a substrate. At this time, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate by a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form an anode Forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer and an electron transporting layer thereon, and then depositing a material usable as a cathode thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

The present disclosure also provides a method of manufacturing an organic light emitting device formed using the coating composition.

Specifically, in one embodiment of the present disclosure, there is provided a method comprising: preparing a substrate; Forming a cathode or an anode on the substrate; Forming at least one organic material layer on the cathode or the anode; And forming an anode or a cathode on the organic material layer, wherein at least one of the organic material layers is formed using the coating composition.

In one embodiment of the present invention, the organic layer formed using the coating composition may be formed using spin coating.

In another embodiment, the organic layer formed using the coating composition is formed by a printing method.

In the state of the present specification, the printing method includes, but is not limited to, ink jet printing, nozzle printing, offset printing, transfer printing, or screen printing.

Since the coating composition according to one embodiment of the present invention has a structural characteristic and is suitable for a solution process, the coating composition can be formed by a printing method, so that there is an economical effect in time and cost in manufacturing a device.

In one embodiment of the present disclosure, the step of forming the organic layer formed using the coating composition comprises: coating the coating composition; And drying the coated coating composition. If necessary, heat treatment or light treatment may be further performed.

In one embodiment of the present invention, the heat treatment temperature in the heat treatment step is 85 캜 to 300 캜.

In another embodiment, the heat treatment time in the heat treatment step may be from 1 minute to 1 hour.

In one embodiment of the present invention, when the coating composition contains no additive, it is preferable that the coating is heat-treated at a temperature of 100 ° C to 300 ° C to perform crosslinking, and crosslinking proceeds at a temperature of 150 ° C to 250 ° C . In addition, the coating compositions herein may further comprise initiators, but are more preferably not used.

In the case where the organic layer formed using the coating composition includes the heat treatment or the light treatment step, an organic layer including a structure in which a plurality of anthracene derivatives included in the coating composition forms a crosslink to form a thin film may be provided. In this case, when another layer is laminated on the surface of the organic material layer formed using the coating composition, it can be prevented that it is dissolved, morphologically affected or decomposed by the solvent.

Therefore, when the organic material layer formed using the coating composition is formed by including the heat treatment or the light treatment step, the resistance to the solvent is increased, so that the multilayer can be formed by repeating the solution deposition and crosslinking method, Life characteristics can be increased.

In one embodiment of the present invention, the coating composition comprising the anthracene derivative of Formula 1 may be prepared by mixing and dispersing the polymer composition in a polymer binder.

In one embodiment of the present invention, the polymer binder is preferably one that does not extremely inhibit charge transport, and that does not strongly absorb visible light. Examples of the polymeric binder include poly (N-vinylcarbazole), polyaniline and derivatives thereof, polythiophene and derivatives thereof, poly (p-phenylenevinylene) and derivatives thereof, poly (2,5-thienylenevinylene) A derivative thereof, a polycarbonate, a polyacrylate, polymethyl acrylate, polymethyl methacrylate, polystyrene, polyvinyl chloride, polysiloxane and the like.

As the anode material, a material having a large work function is preferably used so that injection of holes into the organic material layer is smooth. Specific examples of the anode 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 SNO2: Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.

The cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or LiO2 / Al, but are not limited thereto.

The hole injecting material is a layer for injecting holes from an electrode. The hole injecting material has a hole injecting effect, a hole injecting effect for the anode, an excellent hole injecting effect for a light emitting layer or a light emitting material, A compound which prevents the exciton from migrating to the electron injection layer or the electron injection material and is also excellent in the thin film forming ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.

The hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer and transports holes from the anode or the hole injection layer to the light emitting layer as the hole transport material. The material is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq3); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyanthracene, rubrene, and the like, but are not limited thereto.

The light emitting layer may include a host material and a dopant material. As the host material, the compound of the above-mentioned formula (1) may be used. When an additional host material or an additional light emitting layer is included, a condensed aromatic ring derivative or a heterocyclic compound may be used as the host material. Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.

The electron transporting material is a layer that transports electrons from the electron injecting layer to the electron transporting layer and transports electrons from the electron injecting layer to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode to the light emitting layer. Is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq3; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

The electron injection layer is a layer for injecting electrons from an electrode and has an ability to transport electrons and has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.

The hole blocking layer is a layer which prevents the cathode from reaching the hole, and can be generally formed under the same conditions as the hole injecting layer. Specific examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes and the like.

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

In one embodiment of the present invention, the anthracene derivative may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

Hereinafter, the present invention will be described in detail by way of examples with reference to the drawings. However, the embodiments according to the present disclosure can be modified in various other forms, and the scope of the present specification is not construed as being limited to the embodiments described below. Embodiments of the present disclosure are provided to more fully describe the present disclosure to those of ordinary skill in the art.

< Manufacturing example  1> Synthesis of Formula 1-1

1) Preparation Example 1-1: Synthesis of Intermediate Compound B

                      [Compound A] [Compound B]

(11 mmol) of 1-bromo-4-iodobenzene, 3.48 g (10 mmol) of Compound A and 0.58 g (0.5 mmol) of tetrakispalladium were placed in a round-bottomed flask, 80% by volume of water, and the mixture was stirred at 80 DEG C for 12 hours. The mixture was cooled to room temperature, passed through a celite pad, extracted with ethyl acetate in a separating funnel, and then the solvent was removed by a rotary evaporator. 2.91 g (yield: 63%) of Compound B was obtained by column chromatography.

2) Preparation Example 1-2: Synthesis of Formula 1-1

    [Compound B] [Formula 1-1]

2.3 g (5 mmol) of Compound B and 50 mL of tetrahydropurane were added to a 100 mL round flask and stirred. Compound B was sufficiently dissolved and then cooled to -78 ° C. 2.5 M (2 ml, 5 mmol) of N-butyllithium in hexane solution was added, and the mixture was stirred for 30 minutes. 538 mg (2.5 mmol) of 1,2-bis (chlorodimethylsilyl) ethane was added and the mixture was stirred for 1 hour. After the temperature was raised to room temperature, the mixture was stirred for two hours, and an aqueous ammonium chloride solution was added thereto, followed by stirring for 5 minutes. After extracting with ethyl acetate in a separatory funnel, solvent was removed by rotary evaporator. 2.1 g (yield: 46%) of the compound (1-1) was obtained through column chromatography. 2 is MS data of formula 1-1.

< Manufacturing example  2> Synthesis of Formulas 1-2

1) Preparation example 2-1: Synthesis of intermediate compound C

                                                   [Compound C]

2.36 g (10 mmol) of p-dibromobenzene and 100 mL of tetrahydrofuran were added to a round flask and stirred. The p-dibromobenzene was sufficiently dissolved and then cooled to -78 ° C. 2.5 M (4 ml, 10 mmol) of N-butyllithium in hexane was added, and the mixture was stirred for 30 minutes. 1.08 g (5 mmol) of 1,2-bis (chlorodimethylsilyl) ethane was added and stirred for 1 hour. After the temperature was raised to room temperature, the mixture was stirred for 2 hours, and then an aqueous ammonium chloride solution was added thereto, followed by stirring for 5 minutes. After extracting with ethyl acetate in a separatory funnel, solvent was removed by rotary evaporator. Column chromatography gave 1.1 g (yield: 48%) of Compound C. Figure 3 is MS data of compound C;

2) Preparation Example 2-2: Synthesis of Intermediate Compound D

        [Compound B] [Compound D]

0.44 g (0.54 mmol) of Pd (dppf) Cl ₂ .DCM and 1.47 g (15 mmol) of potassium acetate were placed in a round flask, and toluene (150 mL) And the mixture was stirred at 90 ° C for 12 hours. After cooling to room temperature, the solution was passed through a celite pad and the solvent was removed using a rotary evaporator. Column chromatography afforded 4.9 g (Yield: 89%) of Compound D. 4 is MS data of compound D. Fig.

3) Preparation Example 2-3: Synthesis of Formula 1-2

    [Compound C] [Compound D]

A solution of 2.74 g (6 mmol) of the compound C, 9.12 g (18 mmol) of the compound D, 0.69 g (0.06 mmol) of tetrakispalladium and 4.98 g (36 mmol) of potassium carbonate in a round flask, and tetrahydrofuran And the mixture was stirred at 80 ° C for 2 hours. The mixture was cooled to room temperature, passed through a celite pad, extracted with ethyl acetate in a separating funnel, and then the solvent was removed by a rotary evaporator. Column chromatography afforded 4.4 g (yield: 74%) of formula 1-2. 5 shows the MS data of the formula 1-2, and that the formula 1-2 was produced by the preparation example 2-3.

PREPARATION EXAMPLE 3 Synthesis of Formulas 1-3

[Compound B] [Formula 1-3]

4.59 g (10 mmol) of Compound B and 100 mL of tetrahydrofuran were added to a 250 mL round flask and stirred. The compound was sufficiently dissolved and then cooled to -78 ° C. 2.5 M (4 ml, 10 mmol) of N-butyllithium in hexane was added, and the mixture was stirred for 30 minutes. 1.28 g (5 mmol) of dichloro (decyl) (methyl) silane was added and stirred for 1 hour. After the temperature was raised to room temperature, the mixture was stirred for two hours, and an aqueous ammonium chloride solution was added thereto, followed by stirring for 5 minutes. After extracting with ethyl acetate in a separatory funnel, solvent was removed by rotary evaporator. 6.2 g (yield: 66%) of the formula 1-3 was obtained by column chromatography. Fig. 6 shows MS data of the formula 1-3, which indicates that the formula 1-3 was produced by the preparation example 3.

&Lt; Experimental Example 1: Production of organic light emitting device >

A glass substrate coated with a thin ITO (indium tin oxide) film having a thickness of 50 nm was immersed in distilled water containing detergent and washed with ultrasonic waves. In this case, Fischer Co. was used as a detergent, and distilled water filtered by a filter of Millipore Co. was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

Using a solution of poly (3,4-ethylenedioxythiophene) / polystyrenesulfonic acid on the ITO transparent electrode thus prepared, a film was formed to a thickness of 50 nm by spin coating and dried on a hot plate at 200 DEG C for 10 minutes, Layer.

A poly (N-vinylcarbazole) solution (PVK) was formed on the hole injection layer to a thickness of 20 nm by a spin coating method and dried on a hot plate at 180 DEG C for 60 minutes to form a hole transporting layer.

Next, a solution containing the compound of Formula 1-1 prepared in Preparation Example 1 (3.0 wt%) and the following [Dp-1] (10.0 wt%) was formed to a thickness of 20 nm by spin coating to form a light emitting layer .

[Dp-1]

This was dried in a nitrogen gas atmosphere at 130 占 폚 for 10 minutes, and lithium fluoride (LiF) was vapor-deposited to a thickness of about 1 nm. Finally, aluminum was vapor-deposited to a thickness of 100 nm to form a cathode.

In the above process, the deposition rate of lithium fluoride was maintained at 0.3 Å / sec for aluminum and 2 Å / sec for aluminum, and the vacuum was maintained at 2 × 10 ^-7 to 5 × 10 ^-6 torr during deposition to fabricate an organic light emitting device .

<Experimental Example 2>

A glass light emitting device was prepared in the same manner as in Experimental Example 1, except that the compound of Formula 1-2 was used in place of the compound of Formula 1-1 in Experimental Example 1.

&Lt; Comparative Example 1 &

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the compound of Formula 1-3 was used in place of the compound of Formula 1-1.

Table 1 shows the device results obtained by using each compound in Experimental Examples 1 and 2 and Comparative Example 1 as a light emitting layer.

Host wavelength Power Efficiency (Cd / A) External quantum efficiency (%) The driving voltage (V) Experimental Example 1 (1-1) 431 nm 4.4 4.2 7.7 Experimental Example 2 1-2 422 nm 4.2 4.1 8.1 Comparative Example 1 1-3 432 nm 2.9 2.7 11.3

As shown in Table 1, when the compound of the present invention is included in the organic material layer of the organic light emitting device, particularly the light emitting layer, it is confirmed that the efficiency is higher than that of Comparative Example 1 and the driving voltage is low.

101: substrate
201: anode
301: Hole injection layer
401: hole transport layer
501: light emitting layer
601: electron transport layer
701: Cathode

Claims (12)

A compound of formula
[Chemical Formula 1]

In Formula 1,
Ar1 and Ar2 are the same or different from each other, and each independently hydrogen; heavy hydrogen; Silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
Ar3 and Ar4 are the same or different and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
a and b are each an integer of 0 to 9,
c and d are each an integer of 1 to 3,
e and f are each an integer of 1 or 2,
Wherein L1 is selected from the following structural formulas,

R1 to R4 are the same or different from each other and each independently hydrogen; heavy hydrogen; Silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or R1 and R2 or R3 and R4 may be bonded to each other to form an aliphatic ring or an aromatic ring,
R6 to R9 and R11 to R18 are the same or different from each other, and each independently hydrogen; heavy hydrogen; Silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
R5 and R19 to R21 are the same or different and each independently represents a substituted or unsubstituted alkylene group; A substituted or unsubstituted cycloalkylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
R10 is a substituted or unsubstituted cycloalkylene group; Or a substituted or unsubstituted arylene group,
R22 is a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted cycloalkylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
m1 to m6 and n1 and n2 each independently represent an integer of 1 to 20,
m7 is an integer of 1 to 20,
L2 and L3 are the same or different from each other, and are each independently a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 2:
(2)

Ar 3, Ar 4, c to f, and L 1 to L 3 in the general formula (2) are as defined in formula (1)
Ar5 to Ar8 are the same or different from each other, and each independently hydrogen; heavy hydrogen; Silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
Ar9 and Ar10 are the same or different from each other, and each independently hydrogen; heavy hydrogen; Silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
g to j are each an integer of 0 to 4; The compound according to claim 1, wherein Ar3 and Ar4 are the same or different from each other and each independently is a direct bond; A substituted or unsubstituted arylene group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 6 to 30 carbon atoms. 3. The compound according to claim 2, wherein Ar9 and Ar10 are the same or different from each other, and each independently hydrogen; Silyl group; A substituted or unsubstituted alkyl group having 2 to 10 carbon atoms; A substituted or unsubstituted C6 to C20 aryl; Or a substituted or unsubstituted heterocyclic group having 6 to 60 carbon atoms. 2. The compound according to claim 1, wherein L2 and L3 are the same or different from each other, and each independently is a direct bond; Or a substituted or unsubstituted arylene group. The compound according to claim 1, wherein the compound represented by formula (1) is represented by any one of the following compounds:

A coating composition comprising a compound according to any one of claims 1 to 6. 8. The coating composition of claim 7, further comprising a luminescent dopant. Cathode;
Anode; And
And at least one organic layer provided between the cathode and the anode,
Wherein at least one of the organic material layers comprises a dried product or a cured product of the coating composition of claim 7. [Claim 11] The organic light emitting device according to claim 9, wherein the organic layer includes a light emitting layer, and the light emitting layer includes a dried product of the coating composition. Preparing a substrate;
Forming a cathode or an anode on the substrate;
Forming at least one organic material layer on the cathode or the anode; And
Forming an anode or a cathode on the organic material layer,
Wherein the forming of the organic material layer includes forming at least one organic material layer using the coating composition of claim 7. 12. The method of claim 11, wherein forming the organic layer formed using the coating composition comprises:
Coating the coating composition; And
Drying the coated coating composition
Wherein the organic light-emitting layer is formed on the substrate.

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