KR102192368B1 - Organic light emitting device - Google Patents

Abstract

The present specification is a cathode; Anode; A light emitting layer provided between the cathode and the anode; And at least one organic material layer provided between the anode and the light emitting layer, wherein the organic material layer between the anode and the light emitting layer comprises an amine compound represented by Formula 1 and a polycyclic compound represented by Formula 2 to provide.

Description

Organic light emitting device {ORGANIC LIGHT EMITTING DEVICE}

The present application relates to an organic light emitting device.

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

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

Korean Patent Application Publication No. 10-2011-0027635

The present specification provides an organic light-emitting device including an amine compound and a polycyclic compound.

An exemplary embodiment of the present specification is a cathode; Anode; A light emitting layer provided between the cathode and the anode; And one or more organic material layers provided between the anode and the light-emitting layer, wherein one or more organic material layers between the anode and the light-emitting layer include an amine-based compound represented by Formula 1 below and a polycyclic compound represented by Formula 2 below. It provides an organic light emitting device.

[Formula 1]

In Formula 1,

R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with each other to form a substituted or unsubstituted ring,

Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

L is a direct bond; Or a substituted or unsubstituted arylene group,

R9 and R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, directly bonded to each other, or linked by -NR-, -CR'R"-, -O-, or -S- to form a ring,

R, R', R", R3 to R8, and R11 to R14 are the same as or different from each other, and each independently hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted silyl group; substituted or unsubstituted alkyl group; A substituted or unsubstituted aryloxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or combined with an adjacent group to form a substituted or unsubstituted ring,

a3 is an integer of 1 to 4, and when a3 is 2 or more, R3 is the same as or different from each other,

a4 is 1 or 2, and when a4 is 2, R4 is the same as or different from each other,

n is an integer of 0 to 3, and when n is 2 or more, L is the same as or different from each other,

[Formula 2]

In Formula 2,

R21, R22, and R31 to R40 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; Halogen group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted alkoxy group,

a21 is an integer of 1 to 3, and when a21 is 2 or more, R21 is the same as or different from each other,

a22 is an integer of 1 to 3, and when a22 is 2 or more, R22 is the same as or different from each other.

In the exemplary embodiment of the present specification, in the organic light-emitting device including the amine-based compound and the polycyclic compound, a driving voltage is lowered and efficiency of the device is improved.

In some exemplary embodiments of the present specification, the lifespan characteristics of the organic light emitting device including the amine compound and the polycyclic compound may be improved.

In the exemplary embodiment of the present specification, the organic light emitting device may include at least one of a hole transport layer, a hole injection layer, a layer for simultaneously injecting and transporting holes, and a hole control layer provided between the anode and the emission layer.

In an exemplary embodiment of the present specification, the amine-based compound represented by Formula 1 may be included in the hole injection layer, and the polycyclic compound represented by Formula 2 may be included in the hole transport layer.

In another exemplary embodiment of the present specification, the amine-based compound represented by Formula 1 is included in the hole injection layer, and the polycyclic compound represented by Formula 2 may be doped into the hole injection layer.

In another exemplary embodiment of the present specification, the amine-based compound represented by Formula 1 may be included in the hole control layer.

1 shows an example of an organic light-emitting device comprising an anode 1, a hole injection layer 2, a hole transport layer 3, a light emitting layer 6, and a cathode 9.
FIG. 2 shows an example of an organic light-emitting device comprising an anode 1, a hole injection layer 2, a light-emitting layer 6, and a cathode 9.
3 shows an example of an organic light-emitting device comprising an anode 1, a hole injection layer 2, a hole transport layer 3, a first hole control layer 4, a light-emitting layer 6, and a cathode 9 .
Figure 4 is composed of an anode (1), a hole injection layer (2), a hole transport layer (3), a first hole control layer (4), a second hole control layer (5), a light emitting layer (6) and a cathode (9). An example of an organic light emitting device is shown.
5 is an organic light-emitting device comprising an anode 1, a hole injection layer 2, a hole transport layer 3, a first hole control layer 4, a light-emitting layer 6, an electron transport layer 8, and a cathode 9 It shows an example of.
6 shows an anode (1), a hole injection layer (2), a hole transport layer (3), a first hole control layer (4), a second hole control layer (5), a light emitting layer (6), an electron control layer (7). , An example of an organic light-emitting device comprising an electron transport layer 8 and a cathode 9 is shown.

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

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

"는 결합하는 위치를 의미한다."In this specification

"Means a bonding position.

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

Means a site bonded to another substituent or a bonding portion.

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

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Alkoxy group; Silyl group; Boron group; Imide group; Alkyl group; Alkenyl group; Aryl group; Amine group; And substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group, or substituted or unsubstituted with two or more substituents connected among the aforementioned substituents. For example, "a substituent to which two or more substituents are connected" may be an arylamine group, an arylakenyl group, and the like.

In an exemplary embodiment of the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Hydroxy group; Carbonyl group; Ester group; Alkoxy group; Silyl group; Boron group; Alkyl group; Alkenyl group; Aryl group; And substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group, or substituted or unsubstituted with two or more substituents connected among the aforementioned substituents.

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

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the ester group oxygen may be substituted with a C 1 to C 40 linear, branched or cyclic chain alkyl group or a C 6 to C 30 aryl group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but it is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the silyl group may be represented by the formula of -SiR _a R _b R _c , wherein R _a , R _b and R _c are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group specifically includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc., but is not limited thereto Does not.

In the present specification, the boron group may be represented by the formula of -BR _a R _b , wherein R _a and R _b are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. Specifically, the boron group includes a dimethyl boron group, a diethyl boron group, a t-butylmethyl boron group, a diphenyl boron group, and a phenyl boron group, but is not limited thereto.

In the present specification, the alkyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3- Dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl And the like, but are not limited to these.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. May be, but is not limited thereto.

Substituents including an alkyl group, an alkoxy group, and other alkyl group moieties described in the present specification include all of the straight chain or branched form.

In the present specification, the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.

In the present specification, the number of carbon atoms of the amine group is not particularly limited, but it is preferably 1 to 30. The amine group may be substituted with the aforementioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof, and specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine Group, phenylamine group, 9,9-dimethylfluorenylphenylamine group, pyridylphenylamine group, diphenylamine group, phenylpyridylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, Dibenzofuranylphenylamine group, 9-methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, etc., but limited to these It is not.

In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, a terphenyl group, or a tetraphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a triphenylenyl group, a fluorenyl group, and the like, but is not limited thereto.

(9,9-디메틸플루오레닐기),

(9-메틸-9-페닐플루오레닐기),

(9,9-디페닐플루오레닐기),

,

,

등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,

(9,9-dimethylfluorenyl group),

(9-methyl-9-phenylfluorenyl group),

(9,9-diphenylfluorenyl group),

,

,

And the like, but are not limited thereto.

In the present specification, the heterocyclic group includes one or more of N, O, P, S, Si, and Se as a heteroatom, and the number of carbons is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. Examples of heterocyclic groups include pyridyl group, pyrrole group, pyrimidyl group, pyridazinyl group, furanyl group, thiophenyl group, imidazole group, pyrazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, Triazole group, oxadiazole group, thiadiazole group, dithiazole group, tetrazol group, pyranyl group, thiopyranyl group, pyrazinyl group, oxazinyl group, thiazinyl group, dioxynyl group, triazinyl group, tetrazinyl group, qui Nolinyl group, isoquinolinyl group, quinolyl group, quinazolinyl group, quinoxalinyl group, naphthyridinyl group, acridyl group, xanthenyl group, phenanthridinyl group, diazanaphthalenyl group, triazindenyl group, indole group , Indolinyl group, indolizinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, benzothiazole group, benzoxazole group, benzimidazole group, phenazinyl group, Imidazopyridine group, phenoxazinyl group, phenanthridine group, phenanthroline group, phenothiazine group, imidazopyridine group, imidazophenanthridine group. Benzoimidazoquinazoline group, benzoimidazophenanthridine group, and the like, but are not limited thereto.

In the present specification, the meaning of bonding with adjacent groups to form a ring means a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with adjacent groups; A substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic heterocycle, a substituted or unsubstituted aromatic heterocycle; Or it means to form a condensed ring of these. The hydrocarbon ring refers to a ring consisting of only carbon and hydrogen atoms, and the hydrocarbon ring may be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocycle may be an aliphatic heterocycle or an aromatic heterocycle. In the present specification, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic hetero ring and aromatic hetero ring may be monocyclic or polycyclic.

In the present specification, the aliphatic hydrocarbon ring is a ring that is not aromatic and refers to a ring consisting only of carbon and hydrogen atoms. Examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like, It is not limited to this.

In the present specification, the aromatic hydrocarbon ring refers to an aromatic ring consisting only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acetapthylene, benzo Fluorene, spirofluorene, and the like, but are not limited thereto. In the present specification, the aromatic hydrocarbon ring may be interpreted as having the same meaning as an aryl group.

In the present specification, the aliphatic heterocycle refers to an aliphatic ring containing at least one heteroatom. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxephan, azocaine , Thiocane, and the like, but are not limited thereto.

In the present specification, the aromatic heterocycle means an aromatic ring containing at least one heteroatom. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parasol, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thia Diazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine , Phenanthridine, diazanaphthalene, dryazainden, indole, indolizine, benzothiazole, benzoxazole, benzoimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzo Carbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, indolocarbazole, indenocarbazole, and the like, but are not limited thereto.

The organic light-emitting device according to an exemplary embodiment of the present specification provides an organic light-emitting device including an amine compound represented by Formula 1 and a polycyclic compound represented by Formula 2 between an anode and an emission layer.

In the amine-based compound represented by Formula 1, since each of the two substituents of fluorene contains N, the ability to inject holes compared to a structure in which N is not included in the substituent or N is included in one of the two substituents. outstanding.

In the amine compound represented by Formula 1, a substituent is substituted on carbons 2 and 3 of fluorene, respectively. The organic light-emitting device including the compound of the present application may have characteristics of low voltage and high efficiency compared to an organic light-emitting device having a structure in which a substituent group is not substituted on carbons 2 and 3 of fluorene.

The polycyclic compound represented by Formula 2 may be used as a dopant material for a hole injection layer by substituting a substituted or unsubstituted phenyl group on indenoindene.

Hereinafter, a preferred embodiment of the present invention will be described in detail. However, exemplary embodiments of the present invention may be modified in various forms, and the scope of the present invention is not limited to the exemplary embodiments described below.

In the exemplary embodiment of the present specification, R'and R" are the same as or different from each other, and each independently hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted silyl group; substituted or unsubstituted carbon number 1 To 20 alkyl group; substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms; substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or bonded to each other To form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted ring.

In the exemplary embodiment of the present specification, R'and R" are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group, or are bonded to each other to be substituted or Form an unsubstituted ring.

According to an exemplary embodiment of the present specification, R'and R" are the same as or different from each other, and each independently hydrogen; deuterium; an alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium or an aryl group; or an alkyl group or an aryl group substituted Or an unsubstituted aryl group having 6 to 20 carbon atoms, or combined with each other to form a hydrocarbon ring having 6 to 18 carbon atoms substituted or unsubstituted with an alkyl group or an aryl group.

In another exemplary embodiment, R'and R" are the same as or different from each other, and each independently a methyl group; Or a phenyl group.

In the exemplary embodiment of the present specification, R'is a methyl group.

In the exemplary embodiment of the present specification, R" is a methyl group.

In an exemplary embodiment of the present specification, R is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, R is hydrogen; heavy hydrogen; An alkyl group unsubstituted or substituted with deuterium, an aryl group, or a heterocyclic group; An aryl group unsubstituted or substituted with deuterium, an alkyl group, an aryl group or a heterocyclic group; Or a heterocyclic group unsubstituted or substituted with deuterium, an alkyl group, an aryl group, or a heterocycle.

In an exemplary embodiment of the present specification, R is hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heterocyclic group.

In an exemplary embodiment of the present specification, R is hydrogen; heavy hydrogen; An alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with an aryl group; Or an aryl group having 6 to 24 carbon atoms unsubstituted or substituted with an alkyl group or an aryl group.

In the exemplary embodiment of the present specification, R is a substituted or unsubstituted phenyl group.

In the exemplary embodiment of the present specification, R is a phenyl group.

In the exemplary embodiment of the present specification, R1 and R2 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, or combine with each other to form a substituted or unsubstituted hydrocarbon ring.

In the exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C30 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or combined with each other to form a substituted or unsubstituted hydrocarbon ring.

In another exemplary embodiment, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted quarterphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted pyrenyl group; Or a substituted or unsubstituted chrysenyl group, or combine with each other to form a substituted or unsubstituted fluorene. Here, when R1 and R2 are bonded to each other to form fluorene, the fluorene forms a spiro bond with a fluorene structure to which R1 and R2 are connected.

In another exemplary embodiment, R1 and R2 are the same as or different from each other, and each independently a methyl group or a phenyl group.

In the exemplary embodiment of the present specification, n is an integer of 1 to 3.

In the exemplary embodiment of the present specification, n is 1.

In the exemplary embodiment of the present specification, L is a direct bond; Or a substituted or unsubstituted C6-C24 arylene group.

According to an exemplary embodiment of the present specification, L is a direct bond; Or a substituted or unsubstituted C6-C18 arylene group.

According to an exemplary embodiment of the present specification, L is a direct bond; Or a substituted or unsubstituted C6-C14 arylene group.

In another exemplary embodiment, L is a direct bond; Or any one selected from the following structures.

In the exemplary embodiment of the present specification, L is a direct bond; Or a substituted or unsubstituted phenylene group.

In the exemplary embodiment of the present specification, L is a direct bond; Or a phenylene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group.

In the exemplary embodiment of the present specification, L is a phenylene group.

In the exemplary embodiment of the present specification, L is a p-phenylene group.

In Formula 1, when L is a substituted or unsubstituted arylene group as compared to a direct bond, it is easy in the manufacturing process, and stability of the compound can be improved.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group including a substituted or unsubstituted 6-membered ring; Or a heterocyclic group including a substituted or unsubstituted 6-membered ring.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group including a substituted or unsubstituted 6-membered ring; Or a heterocyclic group containing at least one atom among N, O, and S and including a substituted or unsubstituted 6-membered ring.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or a substituted or unsubstituted C2 to C30 heterocyclic group.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2-C24 heterocyclic group including at least one atom among N, O, and S.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted tetraphenyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted pyrenyl group; A substituted or unsubstituted chrysenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted carbazolyl group; A substituted or unsubstituted dibenzofuranyl group; Or a substituted or unsubstituted dibenzothiophenyl group.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently an alkyl group, an aryl group, or a phenyl group unsubstituted or substituted with a heterocyclic group; A biphenyl group unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group; Terphenyl group unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group; A tetraphenyl group unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group; A phenanthrenyl group unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group; A triphenylenyl group unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group; A fluorenyl group unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group; A naphthyl group unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group; A carbazolyl group unsubstituted or substituted with an alkyl group, an aryl group or a heterocyclic group; A dibenzofuranyl group unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group; Or a dibenzothiophenyl group unsubstituted or substituted with an alkyl group, an aryl group or a heterocyclic group.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group, a biphenyl group, a terphenyl group, a triphenylenyl group, a naphthyl group, a phenalthrenyl group, a dibenzofuranyl group, and a dibenzo. A phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a thiophenyl group; A biphenyl group unsubstituted or substituted with one or more of the phenyl group and the biphenyl group; A terphenyl group unsubstituted or substituted with a phenyl group; Tetraphenyl group; Phenanthrenyl group; Triphenylenyl group; A fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; Naphthyl group; A carbazolyl group unsubstituted or substituted with a phenyl group; Dibenzofuranyl group; Or a dibenzothiophenyl group.

In the exemplary embodiment of the present specification, R3 to R8 and R11 to R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted chain alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group to form a substituted or unsubstituted ring.

In the exemplary embodiment of the present specification, R3 to R8 and R11 to R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, R3 to R8 and R11 to R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C30 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or combined with an adjacent group to form a substituted or unsubstituted ring.

In another exemplary embodiment, R3 to R8 and R11 to R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted terphenyl group, or combined with an adjacent group to form a substituted or unsubstituted ring.

According to another exemplary embodiment, the R3 to R8 and R11 to R14 are the same as or different from each other, and each independently hydrogen; Methyl group; Or a phenyl group.

According to an exemplary embodiment of the present specification, R3 to R8 and R11 to R14 are the same as or different from each other, and each independently hydrogen or deuterium.

According to an exemplary embodiment of the present specification, R3 is hydrogen or deuterium.

According to an exemplary embodiment of the present specification, R4 is hydrogen or deuterium.

In the exemplary embodiment of the present specification, R5 to R8 are each hydrogen or deuterium.

In the exemplary embodiment of the present specification, R11 to R14 are each hydrogen or deuterium.

According to an exemplary embodiment of the present specification, at least one of R5 to R14 is combined with an adjacent group to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, at least one of R5 to R14 is combined with an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring.

According to an exemplary embodiment of the present specification, at least one of R5 to R14 is bonded to an adjacent group to form a substituted or unsubstituted benzene ring.

According to an exemplary embodiment of the present specification, R5 to R6 are bonded to each other to form a benzene ring.

According to an exemplary embodiment of the present specification, R6 to R7 are bonded to each other to form a benzene ring.

According to an exemplary embodiment of the present specification, R7 to R8 are bonded to each other to form a benzene ring.

In the exemplary embodiment of the present specification, R9 to R10 are each hydrogen or deuterium.

In the exemplary embodiment of the present specification, R31 to R40 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; Halogen group; An alkyl group unsubstituted or substituted with a halogen group; Or a halogen group substituted or unsubstituted alkoxy group.

In the exemplary embodiment of the present specification, R31 to R40 are the same as or different from each other, and are independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Haloalkoxy group; Or a haloalkyl group.

In the exemplary embodiment of the present specification, R31 to R40 are the same as or different from each other, and are independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A haloalkoxy group having 1 to 10 carbon atoms; Or a haloalkyl group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, R31 to R40 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; F; Cl; Br; I; An alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of F, Cl, Br and I; Or an alkoxy group having 1 to 6 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of F, Cl, Br and I.

In the exemplary embodiment of the present specification, R31 to R40 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; F; OCF ₃ ; Or CF ₃ .

In the exemplary embodiment of the present specification, R31 is the same as R36.

In the exemplary embodiment of the present specification, R32 is the same as R37.

In the exemplary embodiment of the present specification, R33 is the same as R38.

In the exemplary embodiment of the present specification, R34 is the same as R39.

In the exemplary embodiment of the present specification, R35 is the same as R40.

In an exemplary embodiment of the present invention, Chemical Formula 2 has a point symmetric structure. The meaning that Formula 2 has a point-symmetric structure means that when Formula 2 on a plane is rotated 180° in a horizontal direction with respect to the plane based on the center point of indenoindene, it completely overlaps with the original Formula 2.

In the exemplary embodiment of the present specification, R21 is hydrogen or deuterium.

In the exemplary embodiment of the present specification, R22 is hydrogen or deuterium.

In an exemplary embodiment of the present specification, Formula 2 is represented by the following Formula 2-A.

[Formula 2-A]

In Formula 2-A,

R21, R22, R31 to R40, a21 and a22 are as defined in Chemical Formula 2.

In the exemplary embodiment of the present specification, R31 is a cyano group or F.

In the exemplary embodiment of the present specification, R32 is F, CN, or OCF ₃ .

In the exemplary embodiment of the present specification, R33 is F, CN, CF ₃ or OCF ₃ .

In the exemplary embodiment of the present specification, R34 is F, CN, or OF ₃ .

In the exemplary embodiment of the present specification, R35 is a cyano group or F.

In the exemplary embodiment of the present specification, R36 is a cyano group or F.

In the exemplary embodiment of the present specification, R37 is F, CN, or OCF ₃ .

In the exemplary embodiment of the present specification, R38 is F, CN, CF ₃ or OCF ₃ .

In the exemplary embodiment of the present specification, R39 is F, CN, or OF ₃ .

In the exemplary embodiment of the present specification, R40 is a cyano group or F.

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

[Formula 1-A]

[Formula 1-B]

[Formula 1-C]

[Formula 1-D]

[Formula 1-E]

[Formula 1-F]

In the formulas 1-A to 1-F,

R15 and R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

The definitions of Ar1, Ar2, L, n, R1 to R8, R11 to R14, R, R', R", a3 and a4 are as defined in Formula 1 above.

In an exemplary embodiment of the present specification, Formula 1-B is represented by the following Formula 1-G.

[Formula 1-G]

In Formula 1-G,

Ar1, Ar2, L, n, R1 to R8, a3 and the definition of a4 are the same as in Formula 1-B,

R17 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

a17 is an integer of 1 to 6, and when a17 is 2 or more, R17 is the same as or different from each other.

In the exemplary embodiment of the present specification, R15 and R16 are the same as or different from each other, and each independently hydrogen or deuterium.

In the exemplary embodiment of the present specification, Formula 1 may be represented by the following Formula 1-H.

[Formula 1-H]

In Formula 1-H,

Definitions of Ar1, Ar2, n, R1 to R14, a3 and a4 are the same as in Formula 1.

In Formula 1, when L is a substituted or unsubstituted arylene group as compared to a direct bond, it is easy in the manufacturing process, and stability of the compound can be improved.

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

In the exemplary embodiment of the present specification, the polycyclic compound represented by Formula 2 is any one selected from the following polycyclic compounds.

The compound according to an exemplary embodiment of the present specification may be prepared by a manufacturing method described below.

In an exemplary embodiment of the present specification, the amine-based compound represented by Chemical Formula 1 may be prepared as shown in General Formula 1. However, the preparation method of the compound of Formula 1 is not limited to the following General Formula 1, and may be prepared by a method known in the art, and the type, position or number of substituents may be changed according to techniques known in the art. I can.

[General Formula 1]

In the general formula 1, the definitions of R1 to R14, a3, a4, L, n, Ar1 and Ar2 are the same as those of Chemical Formula 1.

In an exemplary embodiment of the present specification, the polycyclic compound represented by Chemical Formula 2 may be prepared as shown in General Formula 2. However, the method of preparing the compound of Formula 2 is not limited to the following Formula 2, and the manufacturing method may be different in some reaction steps. In addition, Formula 2 may be prepared by a method known in the art, and the type, position, or number of substituents may be changed according to techniques known in the art.

[General Formula 2]

In General Formula 2, the definitions of R21, R22, R31 to R35, a21 and a22 are the same as those of Formula 2.

In the general formula 2, the substituents of the two phenyl groups substituted on indenoindene are the same as R31 to R35. When a reactant having a is used at the same time, a polycyclic compound represented by Formula 2 can be prepared.

The present invention is a cathode; Anode; A light emitting layer provided between the cathode and the anode; And at least one organic material layer provided between the anode and the light-emitting layer, wherein at least one organic material layer between the anode and the light-emitting layer is an amine compound represented by Formula 1 and a polycyclic compound represented by Formula 2 It provides an organic light emitting device comprising a.

In the present specification, it means that at least one organic material layer between the anode and the emission layer includes the amine-based compound represented by Formula 1 and the polycyclic compound represented by Formula 2, the compounds of Formulas 1 and 2 Both the case where the compounds of Formulas 1 and 2 are included in the same organic material layer and the case where the compounds of Formulas 1 and 2 are included in separate organic material layers are both included.

In an exemplary embodiment of the present invention, the organic material layer 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 is an organic material layer, a hole injection layer, a hole transport layer, a layer that simultaneously injects and transports holes, a hole control layer, an electron transport layer, an electron injection layer, a layer that transports and injects electrons simultaneously, and an electron control layer. It may have a structure including the like.

The organic light emitting device according to an exemplary embodiment of the present invention includes at least one organic material layer selected from the group consisting of a hole transport layer, a hole injection layer, a layer for simultaneously transporting and injecting holes, and a hole control layer between the anode and the emission layer.

The organic light-emitting device according to an exemplary embodiment of the present invention includes at least one organic material layer selected from the group consisting of an electron transport layer, an electron injection layer, a layer that simultaneously transports and injects electrons, and an electron control layer between the cathode and the emission layer.

In an exemplary embodiment of the present invention, the amine-based compound represented by Formula 1 is included in the hole transport layer provided between the anode and the light emitting layer, and the polycyclic compound represented by Formula 2 is between the anode and the hole transport layer. It is included in the hole injection layer provided in the.

It includes at least one hole transport layer between the anode and the emission layer; And one or more hole injection layers, which means that the compound of Formula 1 is included in at least one of the hole transport layers, and the compound of Formula 2 is included in at least one of the hole injection layers. In addition, it means that the compound of Formula 1 is included only in the hole transport layer of the organic material layer, and the compound of Formula 2 is included only in the hole injection layer of the organic material layer.

When the compound of Formula 1 is included in the hole transport layer and the compound of Formula 2 is included in the hole injection layer, charges are generated in the hole injection layer by obtaining holes from the adjacent hole transport layer. Hole injection into the system becomes smooth.

When the compound of Formula 1 is included in the hole injection layer and the compound of Formula 2 is not used in any organic material layer, the hole injection layer is compared to a device in which the compounds of Formulas 1 and 2 are used in one or more organic material layers. Injecting holes into the adjacent layer is not smooth, so the driving voltage of the device increases.

Accordingly, when the compound of Formula 1 is included in the hole injection layer, the hole injection layer may be doped with the compound of Formula 2 as follows. When Formulas 1 and 2 are included in the hole injection layer together, the compound of Formula 2 generates electric charges through electrical interaction with the compound of Formula 1, so that hole injection of the hole injection layer may be facilitated.

In an exemplary embodiment of the present specification, the amine-based compound represented by Formula 1 and the polycyclic compound represented by Formula 2 are included in a hole injection layer provided between the anode and the emission layer. In another exemplary embodiment of the present specification, the organic light-emitting device further includes a hole transport layer including an amine-based compound represented by Formula 1 provided between the emission layer and the hole injection layer.

In the hole injection layer including the amine compound represented by Formula 1 and the polycyclic compound represented by Formula 2, the amine compound represented by Formula 1 is a host, and the polycyclic compound represented by Formula 2 is a dopant. Included in the injection layer.

In an exemplary embodiment of the organic light emitting device included in the hole injection layer provided between the anode and the emission layer, the amine compound represented by Formula 1 and the polycyclic compound represented by Formula 2, represented by Formula 2 The polycyclic compound is included in the hole injection layer in an amount of 1 to 40 parts by weight based on 100 parts by weight of the amine compound represented by Chemical Formula 1.

In an exemplary embodiment of the organic light emitting device included in the hole injection layer provided between the anode and the emission layer, the amine compound represented by Formula 1 and the polycyclic compound represented by Formula 2, represented by Formula 2 The polycyclic compound is included in the hole injection layer in an amount of 1 to 30 parts by weight based on 100 parts by weight of the amine compound represented by Chemical Formula 1.

The degree of doping of the compound of Formula 2 may vary depending on the embodiment of the organic light-emitting device, but when 40 parts by weight or more of the compound of Formula 2 is included in the hole injection layer compared to 100 parts by weight of the compound of Formula 1, a lateral current Occurs, the driving voltage of the device increases and the efficiency decreases.

In the exemplary embodiment of the present specification, the amine-based compound represented by Formula 1 is included in one or more hole control layers provided between the anode and the emission layer.

When it is said that the amine compound represented by Formula 1 is included in two or more hole control layers, the amine compound represented by Formula 1 is included in the hole control layer of the first layer, or included in the hole control layer of two or more layers. I can. In the hole control layer that does not contain the amine-based compound represented by Formula 1, other compounds other than the compound of Formula 1 may be included.

In FIG. 1, the structure of an organic light-emitting device including an anode 1, a hole injection layer 2, a hole transport layer 3, a light emitting layer 6, and a cathode 9 is illustrated. In an exemplary embodiment, the amine-based compound of Formula 1 may be included in the hole transport layer 3, and the polycyclic compound of Formula 2 may be included in the hole injection layer 2.

2 illustrates a structure of an organic light-emitting device comprising an anode 1, a hole injection layer 2, a light-emitting layer 6, and a cathode 9. In an exemplary embodiment, the amine-based compound of Formula 1 and the polycyclic compound of Formula 2 may be included in the hole injection layer 2. In an exemplary embodiment, the amine compound of Formula 1 is included as a host in the hole injection layer 2, and the polycyclic compound of Formula 2 is included as a dopant in the hole injection layer 2.

3 illustrates the structure of an organic light-emitting device comprising an anode 1, a hole injection layer 2, a hole transport layer 3, a first hole control layer 4, a light emitting layer 6, and a cathode 9 . In an exemplary embodiment, the amine compound of Formula 1 may be included in the first hole control layer. In an exemplary embodiment, the amine-based compound of Formula 1 is included in the first hole control layer, and the polycyclic compound of Formula 2 is the hole injection layer 2, the hole transport layer 3, or the first hole control layer. It may be included in at least one of the layers 4.

4 shows an anode (1), a hole injection layer (2), a hole transport layer (3), a first hole control layer (4), a second hole control layer (5), a light emitting layer (6) and a cathode (9). The structure of the organic light emitting device is illustrated. In an exemplary embodiment, the amine-based compound of Formula 1 may be included in the first hole control layer 4. In another embodiment, the amine-based compound of Formula 1 may be included in the second hole control layer 5.

5 shows an organic light-emitting device comprising an anode 1, a hole injection layer 2, a hole transport layer 3, a first hole control layer 4, a light-emitting layer 6, an electron transport layer 8, and a cathode 9 The structure of is illustrated. The amine compound of Formula 1 and the polycyclic compound of Formula 2 may be included in the same organic material layer or in different organic material layers. In an exemplary embodiment, the amine-based compound of Formula 1 may be included in the hole transport layer 3, and the polycyclic compound of Formula 2 may be included in the hole injection layer 2.

6 shows an anode (1), a hole injection layer (2), a hole transport layer (3), a first hole control layer (4), a second hole control layer (5), a light emitting layer (6), and an electron control layer (7). , The structure of an organic light-emitting device comprising an electron transport layer 8 and a cathode 9 is illustrated. In an exemplary embodiment, the compound of Formula 1 may be included in the hole transport layer 3 and the compound of Formula 2 may be included in the hole injection layer 2. In another exemplary embodiment, the compounds of Formula 1 and Formula 2 may be included in the hole injection layer 2.

In an exemplary embodiment, 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.

The organic light-emitting device of the present specification may be manufactured by sequentially laminating a cathode, an organic material layer, and an anode on a substrate. In this case, by using a physical vapor deposition method (PVD, physical vapor deposition) such as sputtering or e-beam evaporation, a metal or a conductive metal oxide or an alloy thereof is deposited on the substrate. It can be manufactured by forming an anode, 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 such a method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition, the compound of Formula 1 Formula 2 may be formed as 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, spray method, 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 (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

As the anode material, a material having a large work function is preferred so that holes can be smoothly injected into the organic material layer. Specific examples of the 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); Combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.

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

The hole injection layer is a layer that injects holes from the electrode, and has the ability to transport holes as a hole injection material, and thus has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and is generated from the light emitting layer. A compound that prevents the movement of excitons to the electron injection layer or the electron injection material and has excellent thin film formation ability is preferable.

In an exemplary embodiment of the present invention, when two or more hole injection layers are included in the organic material layer, a hole injection layer that does not contain the compounds of Formulas 1 and 2 may be included. In this case, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material other than the compounds of Formulas 1 and 2 is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, perylene There are a series of organic substances, anthraquinone, and polyaniline and a polythiophene series of conductive polymers, 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 emission layer.

In an exemplary embodiment of the present invention, when two or more hole transport layers are included in the organic material layer, a hole transport layer that does not contain the compound of Formula 1 may be included. In this case, as a hole transport material other than the compound of Formula 1, a material capable of transporting holes from the anode or the hole injection layer and transferring them to the emission layer, and a material having high mobility for holes is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.

The hole control layer is a layer that prevents the flow of electrons from the light emitting layer to the anode and controls the flow of holes flowing into the light emitting layer to control the performance of the entire device. The hole control material is preferably a compound having the ability to prevent the inflow of electrons from the light emitting layer to the anode and control the flow of holes injected into the light emitting layer or the light emitting material. In the exemplary embodiment of the present specification, the compound represented by Formula 1 described above is used in the hole control layer.

The hole control layer is located between the light emitting layer and the anode, and is preferably provided in direct contact with the light emitting layer. In one embodiment, when the device includes a hole control layer of one layer, the hole control layer is provided in direct contact with the emission layer. In an exemplary embodiment, when the device includes two or more hole control layers, at least one of the two or more hole control layers is provided in direct contact with the emission layer.

The light-emitting material is a material capable of emitting light in a visible light region by transporting and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

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

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

The electron control layer is a layer that blocks the inflow of holes from the emission layer to the cathode and controls electrons flowing into the emission layer to control the performance of the entire device. The electron controlling material is preferably a compound having the ability to prevent the inflow of holes from the light emitting layer to the cathode and control electrons injected into the light emitting layer or the light emitting material. As the electron controlling material, a suitable material may be used according to the configuration of the organic material layer used in the device. The electron control layer is located between the light emitting layer and the cathode, and is preferably provided in direct contact with the light emitting layer.

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

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons as the electron injection material, has an electron injection effect from the cathode, and has an excellent electron injection effect on the light emitting layer or the light emitting material, and is generated in the light emitting layer A compound that prevents the excitons from moving to the hole injection layer and is excellent in thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metals Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

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

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

Hereinafter, an exemplary embodiment of the present invention is illustrated through examples. However, the embodiments according to the present specification may be modified in various forms, and the scope of the present specification is not limited to the embodiments described below. The embodiments of the present specification are provided to more completely describe the present invention to those having average knowledge in the art.

< Manufacturing Example 1 > Synthesis of A1 to A2

Synthesis of A1

9,9-dimethyl-9H-fluoren-2-amine (150g, 716.7mmol) was added to DMF (400ml) to dissolve, and then N-bromosuccinimide (NBS, 177.98g, 716.7mmol) at 0 ^o C. ) Was slowly added dropwise and stirred at room temperature for 3 hours. After extraction with water and chloroform (CHCl ₃ ) at room temperature, the white solid was recrystallized with hexane to prepare the compound A1 (165 g, yield 80%). (MS[M+H] ⁺ = 289.03)

Synthesis of A2

Compound A2 was prepared in the same manner as in the synthesis of A1, except that 9,9-diphenyl-9H-fluoren-2-amine was used instead of 9,9-dimethyl-9H-fluoren-2-amine. (MS[M+H] ⁺ = 413.33)

< Manufacturing Example 2 > Synthesis of B1 to B7

Synthesis of B1

A1 (46.1g, 159.9mmol) and (4-(diphenylamino)phenyl) boronic acid (48.5g, 167.9mmol) were added to dioxane (300ml), followed by 2M potassium carbonate aqueous solution (100ml), and tetra After adding kistriphenyl-phosphinopalladium (3.6 g, 2 mol%), the mixture was heated and stirred for 10 hours. After lowering the temperature to room temperature and terminating the reaction, the aqueous potassium carbonate solution was removed to separate the layers. After removal of the solvent, the white solid was recrystallized with hexane to prepare the compound B1 (57.8 g, yield 80%). (MS[M+H] ⁺ = 453.6)

Synthesis of B2

Compound B2 was prepared in the same manner as in the synthesis of B1, except that (4-(9H-carbazol-9-yl)phenyl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid. (MS[M+H] ⁺ = 451.59)

Synthesis of B3

Compound B3 was prepared in the same manner as in the synthesis of B1, except that (4-(10H-phenoxazin-10-yl)phenyl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid. (MS[M+H] ⁺ = 467.58)

Synthesis of B4

Compound B4 was prepared in the same manner as in the synthesis of B1, except that (4-(10H-phenocthiazin-10-yl)phenyl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid. . (MS[M+H] ⁺ = 483.65)

Synthesis of B5

The same method as the synthesis of B1, except that (4-(9,9-dimethylacridin-10(9H)-yl)phenyl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid. To prepare compound B5. (MS[M+H] ⁺ = 493.67)

Synthesis of B6

Compounds in the same manner as in the synthesis of B1, except that (4-(10-phenylphenazine-5(10H)-yl)-phenyl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid. Prepared B6. (MS[M+H] ⁺ = 542.70)

Synthesis of B7

Compound B7 in the same manner as in the synthesis of B1, except that (4-(11H-benzo[a]carbazol-11-yl)phenyl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid. Was prepared. (MS[M+H] ⁺ = 501.65)

< Manufacturing example 3> Synthesis of C1 to C5

Synthesis of C1

Compound C1 was prepared in the same manner except that A2 was used instead of A1 in the synthesis of B1. (MS[M+H] ⁺ = 577.74)

Synthesis of C2

Compound C2 was prepared in the same manner except that A2 was used instead of A1 in the synthesis of B2. (MS[M+H] ⁺ = 575.73)

Synthesis of C3

Compound C3 was prepared in the same manner, except that A2 was used instead of A1 in the synthesis of B3. (MS[M+H] ⁺ = 591.73)

Synthesis of C4

Compound C4 was prepared in the same manner except that A2 was used instead of A1 in the synthesis of B4. (MS[M+H] ⁺ = 607.79)

Synthesis of C5

Compound C5 was prepared in the same manner except for using A2 instead of A1 in the synthesis of B7. (MS[M+H] ⁺ = 625.79)

< Manufacturing example 4> Synthesis of Compound 1-1 to Compound 1-17

Synthesis of compound 1-1

Compound B1 (20g, 37.82mmol), 4-bromo-1,1'-biphenyl (17.8g, 76.39mmol), and sodium-t-butoxide (10.17g, 105.8mmol) were added to xylene. After heating and stirring, reflux and add [bis(tri-t-butylphosphine)]palladium (386mg, 2mol%). After lowering the temperature to room temperature and terminating the reaction, compound 1-1 was prepared by recrystallization using tetrahydrofuran and ethyl acetate. (MS[M+H] ⁺ = 757.99)

Synthesis of compound 1-2

compound Int Synthesis of .1

Compound B1 (30g, 66.28mmol), 1-bromonaphthalene (13.7g, 66.28mmol), sodium-t-butoxide (8.92g, 92.8mmol) was added to toluene, stirred with heating, and refluxed [1,1' -Add bis(diphenylphosphino)ferrocene]dichloropalladium (338mg, 1mol%). After lowering the temperature to room temperature and terminating the reaction, compound int.1 (32.6g, yield 85%) was prepared by recrystallization using tetrahydrofuran and ethyl acetate. (MS[M+H] ⁺ = 579.76)

Synthesis of compound 1-2

In the synthesis of compound 1-1, compound 1-2 was prepared by synthesizing in the same manner, except that iodobenzene was used instead of 4-bromo-1,1′-biphenyl. (MS[M+H] ⁺ = 655.86)

Synthesis of compound 1-3

compound Int Synthesis of .2

In the synthesis of int.1, compound int.2 was prepared by synthesizing in the same manner except that 4-bromobiphenyl was used instead of 1-bromonaphthalene. (MS[M+H] ⁺ = 605.8)

Synthesis of compound 1-3

In the synthesis of compound 1-2, compound 1 was synthesized in the same manner except that int.2 was used instead of int.1 and 2-bromo-9,9-dimethyl-9H-fluorene was used instead of iodobenzene. 3 was prepared. (MS[M+H] ⁺ = 798.06)

Compounds 1-4 and 1- 5 of synthesis

compound Int Synthesis of .3

In the synthesis of int.1, a compound int.3 was prepared by synthesizing in the same manner except that B2 was used instead of B1 and iodobenzene was used instead of 1-bromonaphthalene. (MS[M+H] ⁺ = 527.68)

Synthesis of compound 1-4

In the synthesis of compound 1-2, compound 1 was synthesized in the same manner except that int.3 was used instead of int.1 and 2-bromo-9,9-diphenyl-9H-fluorene was used instead of iodobenzene. -4 was prepared. (MS[M+H] ⁺ = 844.37)

Synthesis of compound 1-5

In the synthesis of compound 1-2, compound 1 was synthesized in the same manner except that int.3 was used instead of int.1 and 4-(4-chlorophenyl)dibenzo[b,d]furan was used instead of iodobenzene. -5 was prepared. (MS[M+H] ⁺ = 769.96)

Synthesis of compounds 1-6 and 1-7

compound Int Synthesis of .4

In the synthesis of int.1, compound int.4 was prepared by synthesizing in the same manner except that B3 was used instead of B1 and iodobenzene was used instead of 1-bromonaphthalene. (MS[M+H] ⁺ = 543.68)

compound Int Synthesis of .5

In the synthesis of int.1, compound int.5 was prepared by synthesizing in the same manner as B3 instead of B1 and 4-bromobiphenyl instead of 1-bromonaphthalene. (MS[M+H] ⁺ = 619.78)

Synthesis of compound 1-6

In the synthesis of compound 1-2, int.4 instead of int.1 and 4-bromo-1,1':4',1"-terphenyl instead of iodobenzene were synthesized in the same manner. Compound 1-6 was prepared (MS[M+H] ⁺ = 771.98)

Synthesis of compound 1-7

In the synthesis of compound 1-2, compound 1 was synthesized in the same manner except that int.5 was used instead of int.1 and 2-bromo-9,9-dimethyl-9H-fluorene was used instead of iodobenzene. Prepared 7. (MS[M+H] ⁺ = 812.04)

Synthesis of compound 1-8

Synthesis of compound Int.6

In the synthesis of int.1, compound int.6 was prepared by synthesizing in the same manner except that B4 was used instead of B1 and iodobenzene was used instead of 1-bromonaphthalene. (MS[M+H] ⁺ = 559.74)

Synthesis of compound 1-8

In the synthesis of compound 1-2, compound 1-8 was prepared by synthesizing in the same manner as int.6 instead of int.1 and 2-(4-chlorophenyl)naphthalene was used instead of iodobenzene. (MS[M+H] ⁺ = 762.00)

Synthesis of compounds 1-9

In the synthesis of compound 1-2, compound 1-9 was prepared by synthesizing in the same manner except that B5 was used instead of int.1 and 3-bromo-biphenyl was used instead of iodobenzene. (MS[M+H] ⁺ = 798.06)

Synthesis of compounds 1-10

Synthesis of compound Int.7

In the synthesis of int.1, compound int.7 was prepared by synthesizing in the same manner except that B6 was used instead of B1 and iodobenzene was used instead of 1-bromonaphthalene. (MS[M+H] ⁺ = 618.8)

Synthesis of compounds 1-10

In the synthesis of compound 1-2, compound 1-10 was synthesized in the same manner except that int.7 was used instead of int.1 and 9-bromophenanthrene was used instead of iodobenzene. (MS[M+H] ⁺ = 795.01)

Synthesis of compound 1-11

In the synthesis of compound 1-2, compound 1-11 was prepared by synthesizing in the same manner, except that B7 was used instead of int.1. (MS[M+H] ⁺ = 693.84)

Synthesis of compounds 1-12 and 1-13

Synthesis of compounds 1-12

In the synthesis of compound 1-2, compound 1-12 was prepared by synthesizing in the same manner except that C1 was used instead of int.1 and 4-bromo-biphenyl was used instead of iodobenzene. (MS[M+H] ⁺ = 882.14)

compound Int Synthesis of .8

In the synthesis of int.1, compound int.8 was prepared by synthesizing in the same manner except that C1 was used instead of B1 and 4-bromobiphenyl was used instead of 1-bromonaphthalene. (MS[M+H] ⁺ = 729.94)

Synthesis of compound 1-13

In the synthesis of compound 1-2, compound 1 was synthesized by the same method except that int.8 was used instead of int.1 and 2-bromo-9,9-dimethyl-9H-fluorene was used instead of iodobenzene. 13 was prepared. (MS[M+H] ⁺ = 922.2)

Synthesis of compounds 1-14

compound Int Synthesis of .9

In the synthesis of int.1, compound int.9 was prepared by synthesizing in the same manner except that C2 was used instead of B1 and iodobenzene was used instead of 1-bromonaphthalene. (MS[M+H] ⁺ = 651.83)

Synthesis of compounds 1-14

In the synthesis of compound 1-2, compound 1-14 was synthesized in the same manner except that int.9 was used instead of int.1 and 1-(4-chlorophenyl)naphthalene was used instead of iodobenzene. (MS[M+H] ⁺ = 854.08)

Synthesis of compounds 1-15

compound Int Synthesis of .10

In the synthesis of int.1, compound int.10 was prepared by synthesizing in the same manner except that C3 was used instead of B1 and iodobenzene was used instead of 1-bromonaphthalene. (MS[M+H] ⁺ = 667.82)

Synthesis of compounds 1-15

In the synthesis of compound 1-2, the compound was synthesized in the same manner as int.10 instead of int.1 and 4-(4-chlorophenyl)dibenzo[b,d]thiophene was used instead of iodobenzene. Prepared 1-15. (MS[M+H] ⁺ = 926.16)

Synthesis of compounds 1-16

compound Int Synthesis of .11

In the synthesis of int.1, compound int.11 was prepared by synthesizing in the same manner except that C4 was used instead of B1 and iodobenzene was used instead of 1-bromonaphthalene. (MS[M+H] ⁺ = 683.89)

Synthesis of compounds 1-16

In the synthesis of compound 1-2, int.11 was used instead of int.1 and 4-bromo-1,1':4',1"-terphenyl was used instead of iodobenzene. Compound 1-16 was prepared (MS[M+H] ⁺ = 912.18)

Synthesis of compound 1-17

In the synthesis of compound 1-2, compound 1-17 was prepared by synthesizing in the same manner, except that C5 was used instead of int.1. (MS[M+H] ⁺ = 777.98)

< Manufacturing example 5> Synthesis of Formulas 2-1 to 2-5

Synthesis of D1 to D5

Synthesis of D1

After adding ethyl-2-(4-bromophenyl)acetate (20g, 82mmol) and TiCl ₄ (32.8g, 172mmol) to methylene chloride (280ml), the temperature was stabilized at minus 50℃, and then triethylamine (17, 1g, 169mmol) was added and stirred for 1 hour. Saturated ammonium chloride (150ml) was added, extracted with methylene chloride, and the solvent was removed under reduced pressure. Then, purified by column chromatography (cyclohexane:ethyl acetate = 5:1) to synthesize D1 (17.5g, 50%). (MS[M+H] ⁺ = 485.18)

Synthesis of D2

D1 ((15g, 31mmol) and potassium hydroxide (8.69g, 155mmol) were added to ethanol/water (1:1 volume ratio, 300ml) and stirred under reflux for 4 hours, and then hydrochloric acid (10% w/w). , 100ml) was added dropwise at 0°C and filtered to synthesize D2 (19.9g, 30%) (MS[M+H] ⁺ = 429.08)

Synthesis of D3

D2 ((20g, 46.7mmol) and trifluorosulfonic acid (80ml) were stirred for 18 hours at 75° C. After cooling to room temperature, it was added dropwise to water at 0° C. After extraction with methylene chloride, the solvent was removed and isopropanol D3 (9.1g, 50%) was synthesized by recrystallization from.

Synthesis of D4

In a nitrogen atmosphere, the compound D3 (30g, 76.5mmol), bis (pinacolato) diboron (25.25g, 99.4mmol) and potassium acetate (14.2g, 153mmol) were mixed, dioxane (300ml) was added and stirred while stirring. Heated. In a state of refluxing, bis(dibenzylidineacetone)palladium (1g, 3mol%) and tricyclohexylphosphine (0.98g, 6mol%) were added, followed by heating and stirring for 3 hours. After completion of the reaction, the temperature was lowered to room temperature and then filtered. Water was poured into the filtrate, extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, the above D4 (30.5g, 82%) was prepared by recrystallization from tetrahydrofuran and ethyl acetate. (MS[M+H] ⁺ = 487.18)

Of D5 synthesis

D4 (20g, 41.1mmol), sodium periodate (26.39g, 123.4mmol) and hydrochloric acid (2eq) were added, followed by stirring at room temperature for 4 hours. After completion of the reaction, it was filtered and recrystallized with ethyl acetate to synthesize D5. (MS[M+H] ⁺ = 322.89)

Synthesis of compounds 2-1 to 2-5

Synthesis of E1

Compound E1 was prepared by synthesizing in the same manner except that D3 was used instead of A1 and (4-(trifluoromethyl)phenyl) boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid in the synthesis of B1. I did. (MS[M+H] ⁺ = 619.54)

Synthesis of E2

Compound E2 was prepared by synthesizing in the same manner except that (3,5-bis(trifluoromethyl)phenyl)boronic acid was used instead of (4-(trifluoromethyl)phenyl)boronic acid in the E1 synthesis. . (MS[M+H] ⁺ = 755.54)

Synthesis of E3

In the synthesis of E1, compound E3 was prepared by synthesizing in the same manner except that (4-cyanophenyl) boronic acid was used instead of (4-(trifluoromethyl)phenyl) boronic acid. (MS[M+H] ⁺ = 533.57)

Synthesis of E4

In the E1 synthesis, D5 instead of A1 was synthesized in the same manner, except that 4-bromo-2-(trifluoromethyl)benzonitrile was used instead of (4-(trifluoromethyl)phenyl)boronic acid. Compound E4 was prepared. (MS[M+H] ⁺ =669.56)

Synthesis of E5

In the synthesis of E4, compound E5 was synthesized in the same manner except that 4-bromo-2-(trifluoromethoxy)benzonitrile was used instead of 4-bromo-2-(trifluoromethyl)benzonitrile. Was prepared. (MS[M+H] ⁺ = 701.56)

Synthesis of compound 2-1

E1 (10g, 16.1mmol), beta-alanine (1g, 0.25eq) and malononitrile (10g, 10eq) were added and stirred at 140° C. for 1 hour to wash the resulting solid with water and ethyl ether. Then, it was recrystallized with acetone and water and filtered. The filtered solid was mixed with N-bromosuccinimide (4.2.g, 24.1 mmol) dissolved in N-acetonitrile, and then pyridine was added and stirred at room temperature for 72 hours. Recrystallized from chlorobenzene to obtain compound 2-1 (4.96g, 50%).

Synthesis of compound 2-2

In the synthesis of compound 2-1, compound 2-2 was prepared by synthesizing in the same manner, except that E2 was used instead of E1. (MS[M+H] ⁺ = 753.52)

Synthesis of compound 2-3

In the synthesis of compound 2-1, compound 2-3 was prepared by synthesizing in the same manner, except that E3 was used instead of E1. (MS[M+H] ⁺ = 531.55)

Synthesis of compound 2-4

Compound 2-4 was prepared by synthesizing in the same manner except that E4 was used instead of E1 in the synthesis of compound 2-1. (MS[M+H] ⁺ = 667.55)

Synthesis of compound 2-5

In the synthesis of compound 2-1, compound 2-5 was prepared by synthesizing in the same manner, except that E5 was used instead of E1. (MS[M+H] ⁺ = 699.54)

<Example 1>

A glass substrate (corning 7059 glass) coated with a thin film of ITO (indium tin oxide) to a thickness of 1,000 Å was placed in distilled water containing a dispersant and washed with ultrasonic waves. The detergent was manufactured by Fischer Co., and the distilled water was Millipore Co. Distilled water filtered secondarily with the product's filter was used. 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 in the order of isopropyl alcohol, acetone, and methanol, followed by drying.

The compound 2-1 was thermally vacuum deposited to a thickness of 100 Å on the prepared ITO transparent electrode to form a hole injection layer. Compound 1-1 (800Å), which is a material for transporting holes, was vacuum-deposited thereon, and then Compound HT2 was vacuum-deposited on the hole transport layer to a film thickness of 100Å to form a hole control layer. As a light emitting layer, the following host compound BH1 and the following dopant compound BD1 (a weight ratio of 25:1) were vacuum deposited to a thickness of 300 Å. Then, the following compound E1 (300Å) and LiQ were vacuum-deposited at a weight ratio of 1:1 to form an electron transport layer, and then lithium fluoride (LiF) having a thickness of 12Å and aluminum having a thickness of 2,000Å were sequentially deposited on the electron transport layer. Thus, a cathode was formed to manufacture an organic light-emitting device.

In the above process, the deposition rate of the organic material was maintained at 1 Å/sec, the deposition rate of lithium fluoride was 0.2 Å/sec, and the deposition rate was 3 to 7 Å/sec for aluminum.

<Examples 2 to 30>

Example 1 in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of the compound 2-1 for the hole injection layer, and the compound shown in Table 1 was used instead of the compound 1-1 for the hole transport layer. Organic light emitting devices of 2 to 30 were prepared.

<Comparative Examples 1 to 10>

Comparative Example in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of the compound 2-1 for the hole injection layer, and the compound shown in Table 1 was used instead of the compound 1-1 for the hole transport layer. Organic light emitting devices of 1 to 10 were prepared.

Table 1 shows the results of experimenting with organic light-emitting devices manufactured by using each compound as a material for a hole injection layer and a hole transport layer as in Examples 1 to 30 and Comparative Examples 1 to 10.

Experimental example Hole injection layer Hole transport layer Voltage(V) Cd/A
(@20mA/cm ² ) Color coordinates
(x,y) life span
(T95, h) Example 1 Compound 2-1 Compound 1-1 3.51 6.71 (0.135, 0.138) 49.0 Example 2 Compound 2-1 Compound 1-2 3.45 6.63 (0.134, 0.137) 50.2 Example 3 Compound 2-1 Compound 1-5 3.41 6.58 (0.135, 0.138) 55.2 Example 4 Compound 2-1 Compound 1-8 3.34 6.82 (0.134, 0.138) 51.2 Example 5 Compound 2-1 Compound 1-9 3.42 6.72 (0.136, 0.139) 48.9 Example 6 Compound 2-1 Compound 1-14 3.31 6.52 (0.135, 0.138) 48.5 Example 7 Compound 2-2 Compound 1-2 3.50 6.69 (0.133, 0.139) 49.1 Example 8 Compound 2-2 Compound 1-3 3.56 6.78 (0.135, 0.138) 50.2 Example 9 Compound 2-2 Compound 1-6 3.48 6.58 (0.134, 0.138) 50.1 Example 10 Compound 2-2 Compound 1-7 3.50 6.67 (0.136, 0.139) 55.0 Example 11 Compound 2-2 Compound 1-11 3.51 6.77 (0.136, 0.139) 53.5 Example 12 Compound 2-2 Compound 1-12 3.42 6.72 (0.135, 0.138) 48.9 Example 13 Compound 2-3 Compound 1-1 3.31 6.52 (0.135, 0.138) 48.5 Example 14 Compound 2-3 Compound 1-3 3.50 6.69 (0.133, 0.139) 49.1 Example 15 Compound 2-3 Compound 1-6 3.48 6.71 (0.134, 0.139) 51.1 Example 16 Compound 2-3 Compound 1-9 3.51 6.66 (0.135, 0.138) 60.0 Example 17 Compound 2-3 Compound 1-12 3.52 6.81 (0.134, 0.138) 55.2 Example 18 Compound 2-3 Compound 1-13 3.55 6.48 (0.136, 0.139) 57.3 Example 19 Compound 2-4 Compound 1-4 3.54 6.38 (0.133, 0.139) 55.2 Example 20 Compound 2-4 Compound 1-5 3.42 6.55 (0.134, 0.139) 53.1 Example 21 Compound 2-4 Compound 1-10 3.51 6.71 (0.135, 0.138) 49.0 Example 22 Compound 2-4 Compound 1-11 3.45 6.63 (0.134, 0.137) 50.2 Example 23 Compound 2-4 Compound 1-13 3.41 6.58 (0.135, 0.138) 55.2 Example 24 Compound 2-4 Compound 1-17 3.34 6.82 (0.134, 0.138) 51.2 Example 25 Compound 2-5 Compound 1-2 3.42 6.72 (0.136, 0.139) 48.9 Example 26 Compound 2-5 Compound 1-4 3.31 6.52 (0.135, 0.138) 48.5 Example 27 Compound 2-5 Compound 1-5 3.50 6.69 (0.133, 0.139) 49.1 Example 28 Compound 2-5 Compound 1-7 3.56 6.78 (0.135, 0.138) 50.2 Example 29 Compound 2-5 Compound 1-10 3.48 6.58 (0.134, 0.138) 50.1 Example 30 Compound 2-5 Compound 1-12 3.50 6.67 (0.136, 0.139) 55.0 Comparative Example 1 HI-1 HT1 4.01 5.12 (0.136, 0.139) 38.0 Comparative Example 2 HI-1 Compound 1-1 3.78 5.88 (0.135, 0.138) 50.0 Comparative Example 3 HI-1 Compound 1-3 3.68 5.98 (0.135, 0.138) 48.0 Comparative Example 4 HI-1 Compound 1-5 3.77 5.78 (0.133, 0.139) 38.0 Comparative Example 5 HI-1 Compound 1-10 3.81 5.66 (0.134, 0.139) 33.0 Comparative Example 6 HI-1 Compound 1-12 3.88 5.77 (0.135, 0.138) 42.0 Comparative Example 7 Compound 2-1 HT1 3.76 5.71 (0.134, 0.138) 44.0 Comparative Example 8 Compound 2-3 HT3 3.61 5.83 (0.136, 0.139) 43.0 Comparative Example 9 Compound 2-4 HT4 3.70 5.88 (0.133, 0.139) 48.0 Comparative Example 10 Compound 2-5 HT5 3.76 5.78 (0.134, 0.139) 50.0

The organic light-emitting devices of Examples 1 to 30 include the compound prepared in Preparation Example 5 in the hole injection layer and the compound prepared in Preparation Example 4 in the hole transport layer. In Table 1, it can be seen that a device in which both compounds are used exhibits characteristics of low voltage and high efficiency compared to a device in which one compound is used or neither compound is used, as in Comparative Example.

The device in which the compound derivative of the formula according to the present invention is mixed can play a role of smooth hole injection and hole transport in organic electronic devices including organic light emitting devices, and the device according to the present invention has an efficiency, driving voltage, and stability. It has excellent properties.

< Example 31>

A glass substrate (corning 7059 glass) coated with a thin film of ITO (indium tin oxide) to a thickness of 1,000 Å was placed in distilled water containing a dispersant and washed with ultrasonic waves. The detergent was manufactured by Fischer Co., and the distilled water was Millipore Co. Distilled water filtered secondarily with the product's filter was used. 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 in the order of isopropyl alcohol, acetone, and methanol, followed by drying.

On the thus prepared ITO transparent electrode, the compound 1-2 (host) synthesized in Preparation Example 4 and the compound 2-1 (dopant) synthesized in Preparation Example 5 were thermally vacuum-deposited at a weight ratio of 80 wt%:20 wt%, and a hole injection layer (Thickness 100Å) was formed. Compound 1-2 synthesized in Preparation Example 4, which is a material for transporting holes, was vacuum-deposited to form a hole transport layer (800 Å), and then HT2 was vacuum-deposited on the hole transport layer to a thickness of 100 Å to form a hole control layer. Formed. A light emitting layer was formed by vacuum depositing a host BH1 and a dopant BD1 compound (25:1 weight ratio) on the hole control layer to a thickness of 300Å. Then, after co-depositing an E1 compound (300Å) and LiQ in a weight ratio of 1:1 to form an electron transport layer, lithium fluoride (LiF) having a thickness of 12 Å and aluminum having a thickness of 2,000 Å were sequentially deposited on the electron transport layer. By forming a cathode, an organic light emitting device was manufactured.

In the above process, the deposition rate of the organic material was maintained at 1 Å/sec, the deposition rate of lithium fluoride was 0.2 Å/sec, and the deposition rate was 3 to 7 Å/sec for aluminum.

< Example 32 to 60>

Instead of compound 1-2 (host) and compound 2-1 (dopant) in the hole injection layer, the compound shown in Table 2 was mixed in the ratio shown in Table 2, and the hole transport layer was used in place of compound 1-2 in Table 2 below. Organic light-emitting devices of Examples 32 to 60 were manufactured in the same manner as in Example 31, except that the compound described in was used.

< Comparative example 11 to 20>

Instead of compound 1-2 (host) and compound 2-1 (dopant) in the hole injection layer, the compound shown in Table 2 was mixed in the ratio shown in Table 2, and the hole transport layer was used in place of compound 1-2 in Table 2 below. Organic light emitting devices of Comparative Examples 11 to 20 were manufactured in the same manner as in Example 31, except that the compound described in was used.

Table 2 shows the results of experimenting with organic light-emitting devices prepared by using each compound as a material for a hole injection layer and a hole transport layer as in Examples 31 to 60 and Comparative Examples 11 to 20. In Example 31 of Table 2 below, in the "Compound 1-2: Compound 2-1 (20wt%)" of the hole injection layer column, Compound 1-2 is used as a host, and Compound 2-1 is used as a dopant, It means that the dopant is contained in 20wt% based on 100wt% of the total weight of the host and the dopant. In Examples 31 to 60 and Comparative Examples 11 to 20, the meaning of the expression is the same as above.

Experimental example Hole injection layer Hole transport layer Voltage(V) Cd/A
(@20mA/cm ² ) Color coordinates
(x,y) life span
(T95, h) Example 31 Compound 1-2: Compound 2-1 (20wt%) Compound 1-2 3.51 6.71 (0.135, 0.138) 49.0 Example 32 Compound 1-3: Compound 2-1 (20wt%) Compound 1-3 3.45 6.63 (0.134, 0.137) 50.2 Example 33 Compound 1-1: Compound 2-1 (20wt%) Compound 1-1 3.41 6.58 (0.135, 0.138) 55.2 Example 34 Compound 1-7: Compound 2-1 (20wt%) Compound 1-7 3.34 6.82 (0.134, 0.138) 51.2 Example 35 Compound 1-9: Compound 2-1 (10wt%) Compound 1-9 3.42 6.72 (0.136, 0.139) 48.9 Example 36 Compound 1-13: Compound 2-1 (30wt%) Compound 1-13 3.31 6.52 (0.135, 0.138) 48.5 Example 37 Compound 1-1: Compound 2-2 (20wt%) Compound 1-1 3.50 6.69 (0.133, 0.139) 49.1 Example 38 Compound 1-5: Compound 2-2 (20wt%) Compound 1-5 3.56 6.78 (0.135, 0.138) 50.2 Example 39 Compound 1-8: Compound 2-2 (20wt%) Compound 1-8 3.48 6.58 (0.134, 0.138) 50.1 Example 40 Compound 1-12: Compound 2-2 (20wt%) Compound 1-12 3.50 6.67 (0.136, 0.139) 55.0 Example 41 Compound 1-14: Compound 2-2 (10wt%) Compound 1-14 3.51 6.77 (0.136, 0.139) 53.5 Example 42 Compound 1-17: Compound 2-2 (30wt%) Compound 1-17 3.42 6.72 (0.135, 0.138) 48.9 Example 43 Compound 1-3: Compound 2-3 (20wt%) Compound 1-3 3.31 6.52 (0.135, 0.138) 48.5 Example 44 Compound 1-4: Compound 2-3 (20wt%) Compound 1-4 3.50 6.69 (0.133, 0.139) 49.1 Example 45 Compound 1-7: Compound 2-3 (20wt%) Compound 1-7 3.48 6.71 (0.134, 0.139) 51.1 Example 46 Compound 1-8: Compound 2-3 (20wt%) Compound 1-8 3.51 6.66 (0.135, 0.138) 60.0 Example 47 Compound 1-10: Compound 2-3 (10wt%) Compound 1-10 3.52 6.81 (0.134, 0.138) 55.2 Example 48 Compound 1-11: Compound 2-3 (30wt%) Compound 1-11 3.55 6.48 (0.136, 0.139) 57.3 Example 49 Compound 1-2: Compound 2-4 (20wt%) Compound 1-2 3.54 6.38 (0.133, 0.139) 55.2 Example 50 Compound 1-4: Compound 2-4 (20wt%) Compound 1-4 3.42 6.55 (0.134, 0.139) 53.1 Example 51 Compound 1-6: Compound 2-4 (20wt%) Compound 1-6 3.51 6.71 (0.135, 0.138) 49.0 Example 52 Compound 1-11: Compound 2-4 (20wt%) Compound 1-11 3.45 6.63 (0.134, 0.137) 50.2 Example 53 Compound 1-16: Compound 2-4 (10wt%) Compound 1-16 3.41 6.58 (0.135, 0.138) 55.2 Example 54 Compound 1-17: Compound 2-4 (30wt%) Compound 1-17 3.34 6.82 (0.134, 0.138) 51.2 Example 55 Compound 1-3: Compound 2-5 (20wt%) Compound 1-3 3.42 6.72 (0.136, 0.139) 48.9 Example 56 Compound 1-8: Compound 2-5 (20wt%) Compound 1-8 3.31 6.52 (0.135, 0.138) 48.5 Example 57 Compound 1-10: Compound 2-5 (20wt%) Compound 1-10 3.50 6.69 (0.133, 0.139) 49.1 Example 58 Compound 1-11: Compound 2-5 (20wt%) Compound 1-11 3.56 6.78 (0.135, 0.138) 50.2 Example 59 Compound 1-14: Compound 2-5 (10wt%) Compound 1-14 3.48 6.58 (0.134, 0.138) 50.1 Example 60 Compound 1-15: Compound 2-5 (30wt%) Compound 1-15 3.50 6.67 (0.136, 0.139) 55.0 Comparative Example 11 HT1: HI-2 (20wt%) HT1 3.80 5.23 (0.136, 0.139) 40.2 Comparative Example 12 Compound 1-2: HI-2 (20wt%) Compound 1-2 3.77 5.44 (0.135, 0.138) 50.2 Comparative Example 13 Compound 1-3: HI-2 (20wt%) Compound 1-3 3.71 5.38 (0.135, 0.138) 48.3 Comparative Example 14 Compound 1-4: HI-2 (20wt%) Compound 1-4 3.78 5.78 (0.133, 0.139) 38.5 Comparative Example 15 Compound 1-11: HI-2 (20wt%) Compound 1-11 3.81 5.77 (0.134, 0.139) 58.1 Comparative Example 16 Compound 1-16: HI-2 (20wt%) Compound 1-16 3.65 5.50 (0.135, 0.138) 41.1 Comparative Example 17 HT4: Compound 2-2 (20wt%) HT4 3.87 5.48 (0.134, 0.138) 48.2 Comparative Example 18 HT5: Compound 2-2 (30wt%) HT5 3.68 5.61 (0.136, 0.139) 39.5 Comparative Example 19 HT3: Compound 2-3 (10wt%) HT3 3.75 5.89 (0.133, 0.139) 48.1 Comparative Example 20 HT1: Compound 2-1 (20wt%) HT1 3.69 6.02 (0.134, 0.139) 51.2

The organic light-emitting devices of Examples 31 to 60 include the compound prepared in Preparation Example 5 and the compound prepared in Preparation Example 4 in the hole injection layer, and the compound prepared in Preparation Example 4 in the hole transport layer. In Table 2, it can be seen that a device in which both compounds are used exhibits characteristics of low voltage and high efficiency than a device in which one compound is used or neither compound is used, as in Comparative Example.

The device in which the compound derivative of the formula according to the present invention is mixed can play a role of smooth hole injection and hole transport in organic electronic devices including organic light emitting devices, and the device according to the present invention has an efficiency, driving voltage, and stability. It shows excellent properties.

1: anode
2: hole injection layer
3: hole transport layer
4: first hole control layer
5: second hole control layer
6: light emitting layer
7: electron control layer
8: electron transport layer
9: cathode

Claims (12)

Cathode; Anode; A light emitting layer provided between the cathode and the anode; And one or more organic material layers provided between the anode and the light-emitting layer, wherein one or more organic material layers between the anode and the light-emitting layer include an amine-based compound represented by Formula 1 below and a polycyclic compound represented by Formula 2 below. Organic light emitting device:
[Formula 1]

In Formula 1,
R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with each other to form a substituted or unsubstituted ring,
Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
L is a direct bond; Or a substituted or unsubstituted arylene group,
R9 and R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, directly bonded to each other, or linked by -NR-, -CR'R"-, -O-, or -S- to form a ring,
R, R', R", R3 to R8, and R11 to R14 are the same as or different from each other, and each independently hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted silyl group; substituted or unsubstituted alkyl group; A substituted or unsubstituted aryloxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or combined with an adjacent group to form a substituted or unsubstituted ring,
a3 is an integer of 1 to 4, and when a3 is 2 or more, R3 is the same as or different from each other,
a4 is 1 or 2, and when a4 is 2, R4 is the same as or different from each other,
n is an integer of 0 to 3, and when n is 2 or more, L is the same as or different from each other,
[Formula 2]

In Formula 2,
R21 and R22 are the same as or different from each other, and each independently hydrogen; Or deuterium,
R31 to R40 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; F; OCF ₃ ; Or CF ₃ ,
a21 is an integer of 1 to 3, and when a21 is 2 or more, R21 is the same as or different from each other,
a22 is an integer of 1 to 3, and when a22 is 2 or more, R22 is the same as or different from each other. The organic light-emitting device of claim 1, wherein the amine compound represented by Formula 1 is represented by any one of the following Formulas 1-A to 1-F:
[Formula 1-A]

[Formula 1-B]

[Formula 1-C]

[Formula 1-D]

[Formula 1-E]

[Formula 1-F]

In the formulas 1-A to 1-F,
R15 and R16 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
The definitions of Ar1, Ar2, L, n, R1 to R8, R11 to R14, R, R', R", a3 and a4 are as defined in Formula 1 above. The organic light-emitting device of claim 2, wherein the formula 1-B is represented by the following formula 1-G:
[Formula 1-G]

In Formula 1-G,
Ar1, Ar2, L, n, R1 to R8, a3 and the definition of a4 are the same as in Formula 1-B,
R17 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
a17 is an integer of 1 to 6, and when a17 is 2 or more, R17 is the same as or different from each other. The method according to claim 1, wherein L is a direct bond; Or an organic light emitting device which is a substituted or unsubstituted arylene group having 6 to 24 carbon atoms. The method according to claim 1, wherein Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted tetraphenyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted pyrenyl group; A substituted or unsubstituted chrysenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted carbazolyl group; A substituted or unsubstituted dibenzofuranyl group; Or an organic light-emitting device that is a substituted or unsubstituted dibenzothiophenyl group. The organic light-emitting device of claim 1, wherein the amine compound represented by Formula 1 is any one selected from the following amine compounds:

. The organic light-emitting device of claim 1, wherein the polycyclic compound represented by Formula 2 is any one selected from the following polycyclic compounds:

. The method according to claim 1, wherein the amine compound represented by Formula 1 is included in a hole transport layer provided between the anode and the light emitting layer, and the polycyclic compound represented by Formula 2 is a hole provided between the anode and the hole transport layer. An organic light-emitting device that is included in the injection layer. The organic light-emitting device of claim 1, wherein the amine-based compound represented by Formula 1 and the polycyclic compound represented by Formula 2 are included in a hole injection layer provided between the anode and the emission layer. The organic light-emitting device of claim 9, wherein the polycyclic compound represented by Formula 2 is included in the hole injection layer in an amount of 1 to 40 parts by weight based on 100 parts by weight of the amine compound represented by Formula 1. The organic light-emitting device of claim 9, further comprising a hole transport layer including an amine-based compound represented by Formula 1 provided between the emission layer and the hole injection layer. The organic light-emitting device of claim 1, wherein the amine-based compound represented by Formula 1 is included in one or more hole control layers provided between the anode and the emission layer.

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