KR20190014472A - Organic elecroluminescent device - Google Patents

Abstract

The present invention relates to an organic electroluminescent device capable of improving lower driving voltage and/or life characteristics. According to the present invention, the organic electroluminescent device comprises: an anode; a cathode disposed to face the anode; and a light emitting layer disposed between the anode and the cathode.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic electroluminescent device,

The present invention claims the benefit of Korean Patent Application No. 10-2017-0098073 filed on August 2, 2017, filed with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

The present invention relates to an organic electroluminescent device.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out.

Development of a new material for such an organic electroluminescent device has been continuously required.

U.S. Patent Application Publication No. 2004-0251816

The present invention provides an organic electroluminescent device.

Anode; A cathode opposite to the anode; And a light emitting layer provided between the anode and the cathode; Wherein the light emitting layer comprises a first host represented by the following general formula (1) and a second host represented by the following general formula (2).

[Chemical Formula 1]

In Formula 1,

R3 is a substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or a substituent of the following formula (3)

(2)

(3)

In the above Formulas 1 to 3,

는 화학식 1과 결합하는 부위를 의미하고,

Refers to a moiety bonded to formula (1)

R1, R2 and R4 to R7 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A nitrile group; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted hydrocarbon ring in combination with an adjacent group; Or a substituted or unsubstituted heterocycle,

X1 to X7 are the same or different from each other and are each independently CRa or N,

Y1 and Y2 are the same or different and are each independently CRbRc, NRd, O or S,

Y3 is CReRf, NRg, O, or S

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

Ra is hydrogen; heavy hydrogen; A nitrile group; A halogen group; A substituted or unsubstituted aryl group; A heteroaryl group; Arylthioxy group; Or an aryloxy group, or is bonded to R4 to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle,

Rb to Rg are the same or different and are each independently hydrogen; heavy hydrogen; A nitrile group; A halogen group; A substituted or unsubstituted aryl group; Or a heteroaryl group,

a is an integer of 0 to 8,

b, e, and f are each an integer of 0 to 7,

c is 0 or 1,

d is an integer of 0 to 2,

g is an integer of 0 to 5,

b + c is an integer of 0 to 7,

When a, b, d, e, f and g are plural, R 1, R 2 and R 4 to R 7 are the same or different and are independent from each other.

The organic electroluminescent device according to one embodiment of the present invention can be used as a material of the organic material layer in the compounds of the formulas (1) and (2), and by using the same, it is possible to improve the efficiency in the organic electroluminescent device, improve the driving voltage and / This is possible.

In detail, when the compound represented by Formula 1 is used as a single host in the light emitting layer, the HOMO level difference with respect to the adjacent hole transport layer is large, so that a barrier to holes is formed and the hole transport to the light emitting layer is not easy, A light emitting zone is formed adjacent to the transport layer. For this reason, the holes and the electrons are not balanced and the efficiency and lifetime are reduced. By using the hole transporting type second host compound represented by the above formula (2) together, the efficiency and lifetime of the organic light emitting device can be improved.

1 shows an organic electroluminescent device according to an embodiment of the present invention.
2 shows the result of liquid chromatography analysis of Compound 1A.
Figure 3 is the result of the mass spectrum of Compound 1A.

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

The present disclosure relates to an anode; A cathode opposite to the anode; And a light emitting layer provided between the anode and the cathode; Wherein the light emitting layer comprises a first host represented by Formula 1 and a second host represented by Formula 2.

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

In this specification, when a member is located on another member, it includes not only the case where the member is in contact with the other member but also the case where another member exists between the two members.

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

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

As used herein, the term " substituted or unsubstituted " A nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or that at least two of the substituents exemplified above are substituted with a substituent to which they are linked, or have no substituent. For example, the "substituent group to which at least two substituents are connected" may be an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, or the like.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, Cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.

In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, However, the present invention is not limited thereto.

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

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms. Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably 10 to 30 carbon atoms. Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, triphenyl, pyrenyl, phenalenyl, perylenyl, no.

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

,

,

,

,

및

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

,

,

,

,

And

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

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.

In the present specification, the N-arylalkylamine group and the aryl group in the N-arylheteroarylamine group are the same as the aforementioned aryl group.

In the present specification, the heteroaryl group includes at least one non-carbon atom and at least one hetero atom. Specifically, the hetero atom may include one or more atoms selected from the group consisting of O, N, Se and S, and the like. The number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include a thiophene group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, , An isoquinolinyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, Phenanthroline, isoxazolyl group, thiadiazolyl group, phenothiazinyl group, and dibenzofuranyl group, but the present invention is not limited thereto.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroarylamine group having two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the above-mentioned heteroaryl group.

In the present specification, examples of the heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as the examples of the above-mentioned heteroaryl group.

In the present specification, the description of the aryl group described above can be applied, except that the arylene group is a divalent group.

In this specification, the description of the above-mentioned heteroaryl group can be applied except that the heteroarylene group is a divalent group.

According to one embodiment of the present invention, the formula (1) is any one of the following formulas (4) to (6).

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In the above formulas 4 to 6,

Ar is a substituted or unsubstituted terphenyl group; A substituted or unsubstituted phenanthrenyl group; Or a substituted or unsubstituted triphenylene group,

X6 and X7 are the same or different and are each independently CRh or N,

Y < 4 > is NR <

R8 is hydrogen; heavy hydrogen; A nitrile group; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted hydrocarbon ring in combination with an adjacent group; Or a substituted or unsubstituted heterocycle,

Rh and Ri are the same or different and each independently hydrogen; Or a substituted or unsubstituted aryl group,

h is an integer from 0 to 4,

g1 is an integer of 0 to 3,

The definitions of R1 to R4, R7, X1 to X4, a to d, g, and Ra to Rd are as shown in the above formulas (1) and (3).

According to one embodiment of the present disclosure, R1 and R2 are the same or different and each independently hydrogen; heavy hydrogen; A nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present disclosure, R1 and R2 are the same or different and each independently hydrogen; heavy hydrogen; A nitrile group; An alkyl group; An aryl group; Or a heteroaryl group.

According to one embodiment of the present disclosure, R1 and R2 are hydrogen.

According to one embodiment of the present disclosure, R < 3 > is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present disclosure, R3 is a substituted or unsubstituted aryl group.

According to one embodiment of the present disclosure, R 3 is an aryl group substituted or unsubstituted with an alkyl group.

According to one embodiment of the present invention, R3 is a phenyl group substituted or unsubstituted with an alkyl group; A biphenyl group substituted or unsubstituted with an alkyl group; A terphenyl group substituted or unsubstituted with an alkyl group; A phenanthrene group substituted or unsubstituted with an alkyl group; A triphenylene group substituted or unsubstituted with an alkyl group; Or a fluorene group substituted or unsubstituted with an alkyl group.

According to one embodiment of the present disclosure, R3 is a phenyl group; Biphenyl group; A terphenyl group; Phenanthrene; Triphenylene group; Or a dimethylfluorene group.

According to one embodiment of the present disclosure, R3 is a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present disclosure, R3 is a substituted or unsubstituted N, O, or S containing heteroaryl group.

According to one embodiment of the present disclosure, R 3 is a substituted or unsubstituted dibenzofurane group, or a substituted or unsubstituted dibenzothiophene group.

According to one embodiment of the present disclosure, R3 is a substituted or unsubstituted carbazole group.

According to one embodiment of the present invention, R3 is a carbazolyl group substituted or unsubstituted with an aryl group which is substituted or unsubstituted with a deuterium, a nitrile group, an alkyl group, an aryl group, or a heteroaryl group

According to one embodiment of the present invention, R 3 is a carbazole group substituted or unsubstituted with a deuterium, or a phenyl group substituted or unsubstituted with a nitrile group.

According to one embodiment of the present invention, R 3 is a carbazole group substituted or unsubstituted with a phenyl group, a tributyl group, a dibenzofurane group, or a phenyl group substituted or unsubstituted with a dibenzothiophene group.

According to one embodiment of the present invention, R3 is a carbazol group substituted or unsubstituted with a naphthyl group.

According to one embodiment of the present invention, R 3 is a carbazol group substituted or unsubstituted with a dibenzofurane group or a dibenzothiophene group.

According to one embodiment of the present disclosure, the R3 may be selected from the following substituents, and the selected substituents may be substituted or unsubstituted with a phenyl group.

.

.

According to one embodiment of the present disclosure, R4 is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted hydrocarbon ring in combination with an adjacent group; Or a substituted or unsubstituted heterocycle.

According to one embodiment of the present disclosure, R4 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present invention, R4 is an aryl group substituted or unsubstituted with an aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, R4 is an aryl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms; Or a heteroaryl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

According to one embodiment of the present invention, R4 is an aryl group having 6 to 20 carbon atoms, which is substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms; Or a heteroaryl group having 6 to 20 carbon atoms substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

According to one embodiment of the present invention, R4 is an aryl group having 6 to 20 carbon atoms, which is substituted or unsubstituted with a phenyl group; Or a heteroaryl group having 6 to 20 carbon atoms substituted or unsubstituted with a phenyl group.

According to one embodiment of the present invention, R4 is a phenyl group substituted or unsubstituted with a phenyl group; Biphenyl group; A pyridine group; A dibenzofurane group substituted or unsubstituted with a phenyl group; Or a dibenzothiophen group substituted or unsubstituted with a phenyl group.

According to one embodiment of the present disclosure, R5 and R6 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted hydrocarbon ring in combination with an adjacent group; Or a substituted or unsubstituted heterocycle.

According to one embodiment of the present disclosure, R5 and R6 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present disclosure, R5 and R6 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A silyl group substituted or unsubstituted with an aryl group; Or a substituted or unsubstituted aryl group.

According to one embodiment of the present disclosure, R5 and R6 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A silyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C6 to C20 aryl group.

According to one embodiment of the present disclosure, R5 and R6 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A silyl group substituted or unsubstituted with a phenyl group; Or a substituted or unsubstituted C6 to C20 aryl group.

According to one embodiment of the present disclosure, R5 and R6 are the same or different from each other, and each independently hydrogen; heavy hydrogen; Triphenylsilyl groups; A phenyl group; Biphenyl group; A terphenyl group; Or a naphthyl group.

According to one embodiment of the present disclosure, R7 is hydrogen or is bonded to an adjacent group to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle.

According to one embodiment of the present disclosure, R7 is hydrogen or is bonded to an adjacent group to form a substituted or unsubstituted heterocycle with an aryl group.

According to one embodiment of the present invention, R7 is hydrogen or a bond with an adjacent group to form a substituted or unsubstituted heterocycle with an aryl group having 6 to 20 carbon atoms.

According to one embodiment of the present disclosure, R7 is hydrogen, or combines with adjacent groups to form a substituted or unsubstituted heterocycle with a phenyl group.

According to one embodiment of the present disclosure, R7 is hydrogen or forms a heterocycle containing N substituted or unsubstituted with a phenyl group in combination with an adjacent group.

According to one embodiment of the present invention, X1 to X7 are the same or different from each other and each independently CRa or N.

According to one embodiment of the present disclosure, at least one of X1 to X3 is N.

According to one embodiment of the present disclosure, X1 to X3 are all CRa.

According to one embodiment of the present disclosure, Ra is hydrogen.

According to one embodiment of the present invention, Ra is an arylthio group, or an aryloxy group.

According to one embodiment of the present disclosure, Ra is a substituted or unsubstituted hydrocarbon ring which is bonded to R4 adjacent thereto to form a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle.

, 또는

를 형성한다.According to one embodiment of the present disclosure, Ra is bonded to R4 adjacent thereto,

, or

.

The dotted line is a site where the benzene ring of the core is bonded.

According to one embodiment of the present disclosure, Y1 and Y2 are the same or different from each other and are independently CRbRc, NRd, or O.

According to one embodiment of the present disclosure, Y1 and Y2 are the same or different and are each independently NRd.

According to one embodiment of the present disclosure, Y3 is CReRf, NRg, O or S.

According to one embodiment of the present disclosure, Y4 is NRi or O.

According to one embodiment of the present disclosure, Rb and Rc are hydrogen.

According to one embodiment of the present disclosure, Rd is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present disclosure, Rd is hydrogen; heavy hydrogen; Substituted or unsubstituted C6-C20 aryl group.

According to one embodiment of the present disclosure, Rd is hydrogen; heavy hydrogen; A halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms substituted or unsubstituted with a substituted or unsubstituted silyl group.

According to one embodiment of the present disclosure, Rd is hydrogen; heavy hydrogen; A halogen atom, an alkyl group, a substituted or unsubstituted aryl group, or an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with a silyl group substituted or unsubstituted with an aryl group.

According to one embodiment of the present disclosure, Rd is hydrogen; heavy hydrogen; Is an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with F, Cl, Br, I, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a silyl group substituted or unsubstituted with a phenyl group.

According to one embodiment of the present disclosure, Rd is hydrogen; heavy hydrogen; F, Cl, Br, I, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with a triphenylsilyl group.

According to one embodiment of the present disclosure, Rd is hydrogen; heavy hydrogen; Is an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with F, Cl, Br, I, methyl, phenyl, biphenyl, naphthyl or triphenylsilyl.

According to one embodiment of the present disclosure, Rd is hydrogen; heavy hydrogen; A phenyl group substituted or unsubstituted with F, a methyl group, a phenyl group, a biphenyl group, a naphthyl group, or a triphenylsilyl group; A biphenyl group substituted or unsubstituted with F, a methyl group, a phenyl group, a biphenyl group, a naphthyl group, or a triphenylsilyl group; F, a terphenyl group substituted or unsubstituted with a methyl group, a phenyl group, a biphenyl group, a naphthyl group, or a triphenylsilyl group; F, a fluorine group substituted or unsubstituted with a methyl group, a phenyl group, a biphenyl group, a naphthyl group, or a triphenylsilyl group.

According to one embodiment of the present disclosure, Rd is hydrogen.

According to one embodiment of the present invention, Rd is a phenyl group substituted or unsubstituted with F, a phenyl group, a biphenyl group, a naphthyl group, or a triphenylsilyl group.

According to one embodiment of the present invention, Rd is a terphenyl group.

According to one embodiment of the present invention, Rd is a naphthyl group substituted or unsubstituted with a phenyl group or a triphenylsilyl group.

According to one embodiment of the present invention, Rd is a dimethylfluorene group.

According to one embodiment of the present disclosure, Re and Rf are the same 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 heteroaryl group.

According to one embodiment of the present disclosure, Re and Rf are the same or different from each other, and each independently hydrogen; heavy hydrogen; Or an alkyl group.

According to one embodiment of the present disclosure, Re and Rf are the same or different from each other, and each independently hydrogen; heavy hydrogen; Or an alkyl group having 1 to 10 carbon atoms.

According to one embodiment of the present disclosure, Re and Rf are the same or different from each other, and each independently hydrogen; heavy hydrogen; Or a methyl group.

According to one embodiment of the present disclosure, Rg is hydrogen; Or a substituted or unsubstituted aryl group.

According to one embodiment of the present disclosure, Rg is hydrogen; Or a substituted or unsubstituted C6 to C20 aryl group.

According to one embodiment of the present disclosure, Rg is hydrogen; Or a substituted or unsubstituted phenyl group.

According to one embodiment of the present invention, Rg is a phenyl group substituted or unsubstituted with a deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present invention, Rg is substituted with deuterium, a nitrile group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with an alkyl group, or a heteroaryl group containing O or S Or an unsubstituted phenyl group.

According to one embodiment of the present invention, Rg is a phenyl group substituted or unsubstituted with deuterium, a nitrile group, a t-butyl group, a phenyl group, a naphthyl group, a dimethylfluorene group, a dibenzofurane group, or a dibenzothiophene group.

According to one embodiment of the present invention, Rh and Ri are the same or different and each independently hydrogen or a substituted or unsubstituted aryl group.

According to one embodiment of the present disclosure, Rh is hydrogen.

According to one embodiment of the present invention, Ri is an aryl group having 6 to 20 carbon atoms.

According to one embodiment of the present disclosure, Ri is a phenyl group

According to one embodiment of the present disclosure, L is a direct bond; Or a substituted or unsubstituted arylene group.

According to one embodiment of the present disclosure, L is a direct bond; Or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

According to one embodiment of the present disclosure, L is a direct bond.

According to one embodiment of the present invention, L is a substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted naphthylene group.

According to one embodiment of the present invention, L is a substituted or unsubstituted silyl group, or a substituted or unsubstituted phenylene group; A substituted or unsubstituted silyl group, or a biphenylene group substituted or unsubstituted with a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted silyl group, or a naphthylene group substituted or unsubstituted with a substituted or unsubstituted alkyl group.

According to one embodiment of the present invention, L is a silyl group substituted or unsubstituted with a phenyl group, or a phenylene group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms; A silyl group substituted or unsubstituted with a phenyl group, or a biphenylene group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms; Or a silyl group substituted or unsubstituted with a phenyl group, or a naphthylene group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms.

According to one embodiment of the present invention, L is a triphenylsilyl group, or a phenylene group substituted or unsubstituted with a methyl group; Biphenylene group; Or a naphthylene group.

According to one embodiment of the present invention, the formula (1) may be selected from the following compounds.

According to one embodiment of the present invention, the formula (2) may be selected from the following compounds.

According to one embodiment of the present disclosure, the compounds of Formulas 1 and 2 may be prepared according to the following reaction scheme, but are not limited thereto. In the following reaction formula, the kind and number of substituent groups can be determined by appropriately selecting a starting material known to a person skilled in the art. The type of reaction and the reaction conditions may be those known in the art.

The compound represented by the formula (1) can be synthesized by the following method.

X1 to X3 are as defined in the above formula (1)

Rv to Rx are the same or different from each other, and each independently hydrogen; heavy hydrogen; A nitrile group; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

The compound represented by the formula (2) can be synthesized by the following method.

Ry and Rz are the same or different from each other, and each independently hydrogen; heavy hydrogen; A nitrile group; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

Further, the organic electroluminescent device according to the present invention includes an anode; A cathode opposite to the anode; And a light emitting layer provided between the anode and the cathode; The light emitting layer includes a first host represented by Formula 1 and a second host represented by Formula 2.

The organic light emitting device of the present invention can be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that one or more organic compound layers are formed using the above-described compounds.

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

The organic compound layer containing the compound of Formula 1 may have a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. The organic material layer may be formed using a variety of polymeric materials by a method such as a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, Layer.

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

1 shows a structure of an organic light emitting device in which an anode 2, a second organic compound layer 3 containing the compound of Formula 1 and a cathode 4 are sequentially stacked on a substrate 1 Are illustrated.

In one embodiment of the present invention, the organic material layer including the first host and the second host includes at least one of a light emitting layer, an electron injecting layer, an electron transporting layer, and a layer simultaneously performing electron injection and electron transporting, Emitting layer may include the first host and the second host.

In one embodiment of the present invention, the light emitting layer includes the first host and the second host in a weight ratio of 1: 3 to 3: 1.

In one embodiment of the present invention, the light emitting layer includes the first host and the second host in a weight ratio of 1: 2 to 2: 1.

In one embodiment of the present invention, the light emitting layer includes a first host and a second host: dopant in a volume ratio of 95: 5 to 70:30.

In one embodiment of the present invention, the light emitting layer includes a first host and a second host: dopant in a volume ratio of 90:10 to 80:20.

For example, the organic light emitting device according to the present invention may be formed by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form a metal oxide or a metal oxide having conductivity on the substrate, A hole transporting layer, a light emitting layer, an electron transporting layer, and an organic material layer including the compound of Formula 1 or Formula 2 are formed on the anode, and then used as a cathode thereon ≪ / RTI > In addition to such a method, an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

As the anode material, a material having a large work function is preferably used so that injection of holes into the organic material layer is smooth. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methyl compounds), poly [3,4- (ethylene-1,2-dioxy) compounds] (PEDT), polypyrrole and polyaniline.

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

As the hole injecting material, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene , An anthraquinone, and a conductive polymer of polyaniline and a poly-compound, but the present invention is not limited thereto.

As the hole transporting material, a material capable of transporting holes from the anode or the hole injecting layer to the light emitting layer and having high mobility to holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The method for preparing the compound of Formula 1 and the preparation of the organic light emitting device using the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the present invention and the scope of the present invention is not limited thereto.

In the present invention, an iridium phosphorescent dopant can be used as the dopant.

In the present invention, the iridium complex used as a dopant in the light emitting layer is as follows.

In one embodiment of the present invention, the dopant is included in a weight ratio of 1 to 20%.

In one embodiment of the present invention, the dopant is included in a weight ratio of 5 to 15%.

<Synthesis Example>

Preparation of compound P1

(100 g, 335.6 mmol) and (2-chloro-6-fluorophenyl) boronic acid (58.5 g, 335.6 mmol) were dissolved in 800 ml of tetrahydrofuran (THF). To this was added a 2 M solution of sodium carbonate (Na ₂ CO ₃ ) 2 (500 mL) and tetrakis (triphenylphosphine) palladium (0) [Pd (PPh ₃ ) ₄ ] (7.7 g, 6.7 mmol) . After the reaction was completed, the reaction mixture was cooled to room temperature, and the resulting mixture was extracted three times with water and toluene. The toluene layer was separated, dried over magnesium sulfate, filtered and the filtrate was distilled under reduced pressure. The concentrated compound was separated by column chromatography with a 10: 1 hexane: ethyl acetate solution to obtain 120.0 g. A peak was confirmed at M / Z = 283 by mass spectrum measurement of the obtained solid.

Preparation of Compound P2

Biphenyl] -4-ylboronic acid (70.1 g, 353.9 mmol) was added to a solution of 5-bromo-2'- mmol) were dissolved in 800 ml of tetrahydrofuran (THF). To this was added a 2 M solution of sodium carbonate (Na ₂ CO ₃ ) 2 (520 mL) and tetrakis (triphenylphosphine) palladium (0) [Pd (PPh ₃ ) ₄ ] (7.7 g, 6.7 mmol) . After the reaction was completed, the reaction mixture was cooled to room temperature, and the resulting mixture was extracted three times with water and toluene. The toluene layer was separated, dried over magnesium sulfate, filtered and the filtrate was distilled under reduced pressure. Subsequently, recrystallization with ethanol yielded 100.8 g of compound P2. A peak was observed at M / Z = 356 by mass spectrum measurement of the obtained solid.

Preparation of compound P3

Next, to 47.0 g (132 mmol) of the above 2-chloro- [1,1 ': 3', 1 '': 4 '', 1 '''- quaterphenyl] -6'-amine, 480 mL of glacial acetic acid, , And 120 ml of distilled water was added and heated. Then, when the solution became clear, it was cooled to 3 to 4 DEG C, 120 mL of 1.64 M sodium nitrite aqueous solution was added, and the mixture was stirred for 30 minutes. The solution keopeo bromide (CuBr ₂₎ were slowly dropped at 3 to 4 ℃ in 32.6 g of hydrochloric acid in (146 mmol) is dissolved (HCl) 96 m L. Thereafter, the mixture was heated to 45 캜, stirred for 30 minutes, heated to 80 캜 and stirred for 30 minutes. After cooling to room temperature, the organic layer was extracted three times with 75 mL of chloroform. The organic layer was washed with water and aqueous solution of sodium hydrogencarbonate, followed by drying the obtained organic layer over anhydrous sodium sulfate (MgSO _4). After filtration, the solvent was distilled off under reduced pressure, and the residue was recrystallized from ethanol to obtain 41.0 g of a compound P3. A peak was observed at M / Z = 420 by mass spectrum measurement of the obtained solid.

Preparation of compound P4

(100 mmol) of the above 6'-bromo-2-chloro-1,1 ': 3', 1 ": 4" After melting, the temperature around the reactor was maintained at -78 캜. Next, 40 ml of 2.5 M-butyllithium was slowly added dropwise. After completion of the dropwise addition, stirring was carried out for 30 minutes, 22.8 g of 9H-xanthen-9-one was dissolved in 200 ml of purified tetrahydrofuran, and then slowly added dropwise. The reaction solution was maintained at -78 ° C for about 1 hour, then warmed to room temperature and stirred for 12 hours. Diluted hydrochloric acid was added to the reaction solution to terminate the reaction, followed by liquid separation using methylene chloride. The obtained organic layer was dried with magnesium sulfate, filtered, and then distilled under reduced pressure. Next, 400 ml of acetic acid was added, and a catalytic amount of hydrochloric acid was added dropwise, followed by stirring at a reflux temperature for 12 hours. After completion of the reaction, the reaction mixture was cooled to obtain a solid. After filtration, 38.2 g of Compound P4 was obtained by column chromatography. A peak was confirmed at M / Z = 519 by mass spectrum measurement of the obtained solid.

Preparation of compound P5

15.9 g (30 mmol) of the compound represented by the above P4, 8.38 g (33 mmol) of bis (pinacolato) diboron, 8.83 g (90 mol) of potassium acetate and 200 mL of 1,4- dba) ₂ 0.86 g (1.5 mmol) and PCy ₃ 0.84 g (3.0 mmol) was dissolved in 20 mL of 1,4-dioxane and added dropwise. After stirring at reflux for 24 hours, the reaction mixture was cooled to room temperature, 200 mL of distilled water was added, and the mixture was extracted twice with 200 mL of methylene chloride. The obtained organic layer was dried with sodium sulfate (MgSO4). After filtration, the solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography to obtain 10.0 g of a compound P5. A peak was confirmed at M / Z = 611 by mass spectrum measurement of the obtained solid.

Preparation of Compound 1A

The compound P5 (22.6 g, 38 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (10.3 g, 38 mmol) were dispersed in tetrahydrofuran (150 ml) Pd (PPh3) 4] (0.45 g, 1 mol%) was added thereto, and the mixture was refluxed with stirring for 6 hours. A solution of potassium carbonate (aq. K2CO3) (58 ml, 115 mmol) The temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethyl acetate, filtered and dried to give 19.2 g (70.1%) of Compound 1A. A peak was confirmed at M / Z = 716 by mass spectrum measurement of the obtained solid.

2 shows the result of liquid chromatography analysis of Compound 1A.

Figure 3 is the result of the mass spectrum of Compound 1A.

Preparation of Compound 1B

18.8 g (69.2%) of Compound 1B was prepared by the same method as Compound 1A except that 4-chloro-2,6-diphenylpyrimidine (10.1 g, 38 mmol) was used. A peak was confirmed at M / Z = 715 by mass spectrum measurement of the obtained solid.

Preparation of compound P6

(9-phenyl-9H-carbazol-3-yl) boronic acid (101.6 g, 353.9 mmol) was used to obtain 110.4 g of compound P6. Peak was confirmed at M / Z = 445 by mass spectrum measurement of the obtained solid.

Preparation of compound P7

Next, except that 58.7 g (132 mmol) of 2'-chloro-5- (9-phenyl-9H-carbazol-3-yl) - [1,1'- Was prepared in the same manner as the compound P3 to obtain 42.6 g of the compound P7. A peak was confirmed at M / Z = 509 by mass spectrum measurement of the obtained solid.

Preparation of compound P8

Subsequently, except that 50.8 g (100 mmol) of 3- (6-bromo-2'-chloro- [1,1'-biphenyl] -3- Was prepared in the same manner as the compound P4 to give 29.8 g of the compound P8. A peak was confirmed at M / Z = 608 by mass spectrum measurement of the obtained solid.

Preparation of Compound P9

Next, the compound P9 was prepared in the same manner as the compound P5 except that 18.2 g (30 mmol) of the compound represented by P8 was used, to obtain 9.6 g of the compound P9. A peak was confirmed at M / Z = 700 by mass spectrum measurement of the obtained solid.

Preparation of Compound 1C

The compound P9 (26.6 g, 38 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (10.3 g, 38 mmol) were dispersed in tetrahydrofuran (150 ml) Pd (PPh3) 4] (0.45 g, 1 mol%) was added thereto, and the mixture was refluxed with stirring for 6 hours. A solution of potassium carbonate (aq. K2CO3) (58 ml, 115 mmol) The temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethyl acetate, filtered and dried to give 19.2 g (49.7%) of compound 1C. A peak was confirmed at M / Z = 805 by mass spectrum measurement of the obtained solid.

Preparation of Compound 1D

14.0 g (45.8%) of Compound 1D was prepared in the same manner as Compound 1C except that 4-chloro-2,6-diphenylpyrimidine (10.1 g, 38 mmol) was used. A peak was confirmed at M / Z = 804 by mass spectrum measurement of the obtained solid.

Preparation of Compound P11

Compound P10 (110.6 g, 353.9 mmol) was dissolved in 800 ml of toluene. To this was added sodium tertiary-butoxide (54.4 g, 566.2 mmol) and bis (tri-tert-butylphosphine) palladium [Pd (P- t Bu ₃ ) ₂ ] (1.8 g, 3.5 mmol) . After the reaction was completed, the reaction mixture was cooled to room temperature, and the resulting mixture was extracted three times with water and toluene. The toluene layer was separated, dried over magnesium sulfate, filtered and the filtrate was distilled under reduced pressure. Subsequently, 1000 ml of methanol was dissolved, palladium / charcoal was slowly added at room temperature and stirred, 100 ml of hydrazine monohydrate was slowly added dropwise, and the mixture was stirred at reflux for 24 hours. The temperature was lowered to room temperature, the palladium was removed by filtration, and the organic layer was extracted three times with 400 mL of chloroform. The organic layer was washed with water and aqueous solution of sodium hydrogencarbonate, followed by drying the obtained organic layer over anhydrous sodium sulfate (MgSO _4). After filtration, the solvent was distilled off under reduced pressure, and the residue was recrystallized with ethanol to obtain 36.0 g of a compound P11. A peak was confirmed at M / Z = 369 by mass spectrum measurement of the obtained solid.

Preparation of compound P12

Next, the same compound as that of the compound P7 was obtained except that 48.7 g (132 mmol) of 5- (9H-carbazol-9-yl) -2'-chloro- [1,1'- To obtain 30.6 g of the compound P12. A peak was confirmed at M / Z = 433 by mass spectrum measurement of the obtained solid.

Preparation of compound P13

Next, to a solution of the compound P8 and (3-bromo-2'-chloro- [1,1'-biphenyl] -3-yl) The same procedure was followed to obtain 22.4 g of the compound P13. A peak was confirmed at M / Z = 532 by mass spectrum measurement of the obtained solid.

Preparation of compound P14

Next, the compound P9 was prepared in the same manner as the compound P9, except that 16.0 g (30 mmol) of the compound represented by P13 was used, to obtain 8.2 g of the compound P15. A peak was confirmed at M / Z = 624 by mass spectrum measurement of the obtained solid.

Preparation of Compound 1E

The compound P14 (23.7 g, 38 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (10.3 g, 38 mmol) were dispersed in tetrahydrofuran (150 ml) Pd (PPh3) 4] (0.45 g, 1 mol%) was added thereto, and the mixture was refluxed with stirring for 6 hours. A solution of potassium carbonate (aq. K2CO3) (58 ml, 115 mmol) The temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethyl acetate, filtered and dried to give 16.8 g (60.7%) of compound 1E. A peak was observed at M / Z = 729 by mass spectrum measurement of the obtained solid.

Preparation of compound 1F

(31.3%) was prepared by the same method as Compound 1E except that 4-chloro-2,6-diphenylpyrimidine (10.1 g, 38 mmol) was used. A peak was confirmed at M / Z = 728 by mass spectrum measurement of the obtained solid.

Preparation of compound P15

(9-phenyl-9H-carbazol-3-yl) boronic acid (96.3 g, 353.9 mmol) was used to obtain 98.6 g of compound P15. A peak was confirmed at M / Z = 430 by mass spectrum measurement of the obtained solid.

Preparation of compound P16

Next, in the same manner as in the compound P3 except for using 56.7 g (132 mmol) of 2'-chloro-5- (triphenylene-2-yl) - [1,1'- To obtain 34.2 g of the compound P16. A peak was confirmed at M / Z = 494 by mass spectrum measurement of the obtained solid.

Preparation of compound P17

Next, in the same manner as in the case of the compound P4 except that 49.4 g (100 mmol) of 2- (6-bromo-2'-chloro- [1,1'-biphenyl] To obtain 23.0 g of a compound P17. A peak was confirmed at M / Z = 593 by mass spectrum measurement of the obtained solid.

Preparation of compound P18

Next, in the same manner as in the case of the compound P5 except for using 17.8 g (30 mmol) of the compound represented by P17, 9.0 g of the compound P18 was obtained. A peak was confirmed at M / Z = 685 by mass spectrum measurement of the obtained solid.

Preparation of Compound 1G

The compound P18 (26.0 g, 38 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (10.3 g, 38 mmol) were dispersed in tetrahydrofuran (150 ml) Pd (PPh3) 4] (0.45 g, 1 mol%) was added thereto, and the mixture was refluxed with stirring for 6 hours. A solution of potassium carbonate (aq. K2CO3) (58 ml, 115 mmol) The temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethyl acetate, filtered and dried to obtain 17.8 g (59.3%) of Compound 1G. A peak was confirmed at M / Z = 790 by mass spectrum measurement of the obtained solid.

Preparation of Compound 1H

9.8 g (31.3%) of compound 1H was prepared in the same manner as compound 1G except that 4-chloro-2,6-diphenylpyrimidine (10.1 g, 38 mmol) was used. A peak was observed at M / Z = 789 by mass spectrum measurement of the obtained solid.

Preparation of Compound 2A

The compound (9 - ([1,1'-biphenyl] -3- yl) -3-bromo-9H-carbazole (10.8 g, 3-yl) boronic acid (9.8 g, 27 mmol) was dispersed in tetrahydrofuran (80 ml), and a 2M aqueous potassium carbonate solution (aq. K2CO3) (40 ml, 81 mmol), tetrakis triphenylphosphinopalladium [Pd (PPh3) 4] (0.3 g, 1 mol%) was added, and the mixture was refluxed for 6 hours. The temperature was lowered to room temperature, the water layer was removed, and the filtrate was concentrated under reduced pressure. Ethyl acetate was added thereto, and the mixture was stirred under reflux for 1 hour, cooled to room temperature, and filtered. Chloroform was added to the obtained solid, which was dissolved under reflux. Ethyl acetate was added thereto, and 11.2 g (65.1%) of Compound 2A was prepared by recrystallization. A peak was confirmed at M / Z = 637 by mass spectrum measurement of the obtained solid.

Preparation of Compound 2B

(70.0%) of Compound 2B was prepared in the same manner as Compound 2A, except that (9-phenyl-9H-carbazol-3-yl) boronic acid (7.8 g, 27 mmol) was used. A peak was confirmed at M / Z = 561 by mass spectrum measurement of the obtained solid.

Preparation of Compound 2C

The compound (9-phenyl-9H-carbazol-3-yl) -3-bromo-9H- ) Boronic acid (7.8 g, 27 mmol) was dispersed in tetrahydrofuran (80 ml), and a 2M potassium carbonate aqueous solution (aq. K2CO3) (40 ml, 81 mmol) was added, tetrakistriphenylphosphinopalladium Pd (PPh3) 4] (0.3 g, 1 mol%) was added thereto, followed by stirring under reflux for 8 hours. The temperature was lowered to room temperature, the water layer was removed, and the filtrate was concentrated under reduced pressure. Ethyl acetate was added thereto, and the mixture was stirred under reflux for 1 hour, cooled to room temperature, and filtered. Chloroform was added to the obtained solid and dissolved under reflux. Ethyl acetate was added thereto, and recrystallization yielded 9.8 g (64.7%) of compound 2C. A peak was confirmed at M / Z = 561 by mass spectrum measurement of the obtained solid.

Preparation of Compound 2D

The compound 9- ([1,1'-biphenyl] -4-yl) -3-bromo-9H-carbazole (10.8 g, 3-yl) boronic acid (9.8 g, 27 mmol) was dispersed in tetrahydrofuran (80 ml), and a 2M aqueous potassium carbonate solution (aq. K2CO3) (40 ml, 81 mmol) was added, tetrakis triphenylphosphinopalladium [Pd (PPh3) 4] (0.3 g, 1 mol%) was added, and the mixture was refluxed with stirring for 8 hours. The temperature was lowered to room temperature, the water layer was removed, and the filtrate was concentrated under reduced pressure. Ethyl acetate was added thereto, and the mixture was stirred under reflux for 1 hour, cooled to room temperature and filtered. Chloroform was added to the obtained solid, which was dissolved under reflux. Ethyl acetate was added thereto, and 7.2 g (41.9%) of compound 2D was prepared by recrystallization. A peak was confirmed at M / Z = 637 by mass spectrum measurement of the obtained solid.

Example  1 to 16

A thin glass substrate coated with ITO (indium tin oxide) at a thickness of 1,300 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, a Fischer Co. product was used as a detergent, and distilled water, which was filtered with a filter of Millipore Co., was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

The following HI-1 compound was thermally vacuum deposited on the ITO transparent electrode prepared above to a thickness of 50 Å to form a hole injection layer.

The HT-1 compound was thermally vacuum-deposited on the hole injection layer to a thickness of 250 Å to form a hole transport layer, and an HT-2 compound was vacuum deposited on the HT-1 deposition layer to a thickness of 50 Å to form an electron blocking layer.

Then, Compound 1 (host) and Compound 2 (dopant) prepared above were vapor-deposited to a thickness of 400 Å by simultaneous evaporation at a specific volume ratio (ratio shown in Table 1) on the HT-2 vapor deposition film, A phosphorescent dopant GD-1 was co-deposited to form a light emitting layer.

An ET-1 material was vacuum deposited on the light-emitting layer to a thickness of 250 ANGSTROM and an ET-2 material was co-deposited with a 2% weight ratio Li to a thickness of 100 ANGSTROM to form an electron transport layer and an electron injection layer. Aluminum was deposited on the electron injecting layer to a thickness of 1000 to form a cathode.

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

Comparative Example

The organic light emitting devices were fabricated in the same manner as in Example 1, except that the phosphorescent host material and the dopant content in the light emitting layer were changed as shown in Table 1 below. The host materials A and B used in the comparative example are as follows. The current, voltage, efficiency, luminance, color coordinates and lifetime of the organic light-emitting device manufactured in the above-described Examples to Comparative Examples 1 to 5 were measured, and the results are shown in the following table. In this case, T95 is the optical density of 20mA / cm ² Is the time required for the luminance to be reduced to 95% when the initial luminance is 100%.

Comparative Example 1

An OLED device was fabricated in the same manner as in the above example, except that the compound 1A was deposited to a thickness of 400 A and the phosphorescent dopant GD-1 was doped at a weight ratio of 10%.

Comparative Example 2

An OLED device was fabricated in the same manner as in the above example, except that the compound A was deposited to a thickness of 300 A and the phosphorescent dopant GD-1 was doped at a weight ratio of 10%.

Comparative Example 3

OLED devices were fabricated in the same manner as in the above example except that the compound B and the compound PH-1 were vapor-deposited to a thickness of 300 Å at a ratio of 1: 1 by simultaneous evaporation and the phosphorescent dopant GD-1 was doped at a weight ratio of 15% Respectively.

Comparative Example 4

An OLED device was fabricated in the same manner as in the above example, except that compound 1A and compound 1B were simultaneously evaporated at a ratio of 1: 1 to a thickness of 400A and a phosphorescent dopant GD-1 was doped at a weight ratio of 12%.

Comparative Example 5

OLED devices were fabricated in the same manner as in the above example, except that Compound 2A and Compound 2B were simultaneously evaporated at a 1: 1 ratio to a thickness of 400 A and doped with phosphorescent dopant GD-1 at a weight ratio of 10%.

Voltage, EGE, color coordinates, and lifetime were measured for the organic light-emitting devices manufactured in Examples 1 to 16 and Comparative Examples 1 to 5, and the results are shown in Table 1 below.

EGE is a value obtained by measuring the spectral radiance luminance spectrum when the voltage is applied to the device so that the current density becomes 10 mA / cm 2 by the spectral radiance luminance meter CS-1000 (manufactured by Konica Minolta). The external quantum efficiency was calculated on the assumption that the Ranbandian radiation was performed from the obtained spectral radiance luminance spectrum.

No. Host: dopant
(Thickness, A) dopant content Voltage (V)
(@ 10 mA / cm ² ) EQE (%)
(@ 10 mA / cm ² ) Color coordinates
(x, y) Life (T ₉₅ , h)
(@ 20 mA / cm ² ) Example 1 Compound 1A: Compound 2A: GD-1
(200: 200) 12% 3.34 19.5 (0.35, 0.62) 141.0 Example 2 Compound 1C: Compound 2A: GD-1
(200: 200) 12% 3.38 22.0 (0.34, 0.61) 132.0 Example 3 Compound 1E: Compound 2A: GD-1
(200: 200) 12% 3.40 19.2 (0.33, 0.62) 140.0 Example 4 Compound 1G: Compound 2A: GD-1
(200: 200) 12% 3.46 19.0 (0.34, 0.60) 128.0 Example 5 Compound 1A: Compound 2B: GD-1
(200: 200) 12% 3.38 19.7 (0.34, 0.61) 136.0 Example 6 Compound 1C: Compound 2B: GD-1
(200: 200) 12% 3.40 21.8 (0.35, 0.60) 134.0 Example 7 Compound 1E: Compound 2B: GD-1
(200: 200) 12% 3.44 19.4 (0.32, 0.61) 132.0 Example 8 Compound 1G: Compound 2B: GD-1
(200: 200) 12% 3.48 19.6 (0.35, 0.59) 140.0 Example 9 Compound 1A: Compound 2C: GD-1
(200: 200) 12% 3.36 19.8 (0.35, 0.62) 141.0 Example 10 Compound 1C: Compound 2C: GD-1
(200: 200) 12% 3.36 21.8 (0.34, 0.60) 130.0 Example 11 Compound 1E: Compound 2C: GD-1
(200: 200) 12% 3.42 19.0 (0.32, 0.62) 138.0 Example 12 Compound 1G: Compound 2C: GD-1
(200: 200) 12% 3.44 19.2 (0.34, 0.61) 124.0 Example 13 Compound 1A: Compound 2D: GD-1
(200: 200) 12% 3.34 19.4 (0.32, 0.60) 133.0 Example 14 Compound 1C: Compound 2D: GD-1
(200: 200) 12% 3.34 20.0 (0.34, 0.59) 132.0 Example 15 Compound 1E: Compound 2D: GD-1
(200: 200) 12% 3.40 19.8 (0.31, 0.60) 134.0 Example 16 Compound 1G: Compound 2D: GD-1
(200: 200) 12% 3.42 19.2 (0.34, 0.58) 128.0 Comparative Example 1 Compound 1A: GD-1
(400) 10% 2.87 17.2 (0.31, 0.63) 18.9 Comparative Example 2 Compound A: GD-1
(300) 10% 3.64 13.4 (0.38, 0.59) 12.4 Comparative Example 3 Compound B: PH-1: GD-1
(150: 150) 15% 3.22 19.4 (0.32, 0.63) 46.4 Comparative Example 4 Compound 1A: Compound 1B: GD-1
(200: 200) 12% 4.04 15.4 (0.38, 0.60) 11.4 Comparative Example 5 Compound 2A: Compound 2B: GD-1
(200: 200) 10% 5.64 11.6 (0.36, 0.58) 10.6

In Examples 1 to 16 in Table 1, the light emitting layer was formed by depositing Compound 1A and Compound 2A in a volume ratio of 1: 1 (200 ANGSTROM: 200 ANGSTROM) to 400 ANGSTROM, dopant (GD) In Comparative Example 4, Compound 1A and Compound 1B were used instead of Compound 1A and Compound 1B were used as a host. In Comparative Example 5, Compound 2A and Compound 2B were used as a host instead of Compound 1A and Compound 2A.

It can be seen that Examples 1 to 16 have a voltage as low as 40%, EQE as high as 64%, and lifetime as high as 1170% as compared with Comparative Example 4 and Comparative Example 5.

1: substrate
2: anode
3: organic layer
4: Cathode

Claims (6)

Anode; A cathode opposite to the anode; And a light emitting layer provided between the anode and the cathode; Wherein the light emitting layer comprises a first host represented by the following formula 1 and a second host represented by the following formula 2:
[Chemical Formula 1]

In Formula 1,
R3 is a substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or a substituent of the following formula (3)
(2)

(3)

In the above Formulas 1 to 3,

Refers to a moiety bonded to formula (1)
R1, R2 and R4 to R7 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A nitrile group; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted hydrocarbon ring in combination with an adjacent group; Or a substituted or unsubstituted heterocycle,
X1 to X7 are the same or different from each other and are each independently CRa or N,
Y1 and Y2 are the same or different and are each independently CRbRc, NRd, O or S,
Y3 is CReRf, NRg, O, or S
L is a direct bond; Or a substituted or unsubstituted arylene group,
Ra is hydrogen; heavy hydrogen; A nitrile group; A halogen group; A substituted or unsubstituted aryl group; A heteroaryl group; Arylthioxy group; Or an aryloxy group, or is bonded to R4 to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle,
Rb to Rg are the same or different and are each independently hydrogen; heavy hydrogen; A nitrile group; A halogen group; A substituted or unsubstituted aryl group; Or a heteroaryl group,
a is an integer of 0 to 8,
b, e, and f are each an integer of 0 to 7,
c is 0 or 1,
d is an integer of 0 to 2,
g is an integer of 0 to 5,
b + c is an integer of 0 to 7,
When a, b, d, e, f and g are plural, R 1, R 2 and R 4 to R 7 are the same or different and are independent from each other. The organic electroluminescent device according to claim 1, wherein the compound represented by Formula 1 is any one of Formulas 4 to 6:
[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In the above formulas 4 to 6,
Ar is a substituted or unsubstituted terphenyl group; A substituted or unsubstituted phenanthrenyl group; Or a substituted or unsubstituted triphenylene group,
X6 and X7 are the same or different and are each independently CRh or N,
Y &lt; 4 &gt; is NR &lt;
R8 is hydrogen; heavy hydrogen; A nitrile group; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted hydrocarbon ring in combination with an adjacent group; Or a substituted or unsubstituted heterocycle,
Rh and Ri are the same or different and each independently hydrogen; Or a substituted or unsubstituted aryl group,
h is an integer from 0 to 4,
g1 is an integer of 0 to 3,
The definitions of R1 to R4, R7, X1 to X4, a to d, g, and Ra to Rd are as shown in the above formulas (1) and (3). 2. The compound of claim 1, wherein R &lt; 4 &gt; Biphenyl group; A pyridine group; A dibenzofurane group substituted or unsubstituted with a phenyl group; Or a dibenzothiophene group substituted or unsubstituted with a phenyl group, or a substituted or unsubstituted hydrocarbon ring bonded to Ra or an adjacent group; Or a substituted or unsubstituted heterocycle. The organic electroluminescent device according to claim 1, wherein the first host represented by Formula 1 is selected from the following compounds:

The organic electroluminescent device according to claim 1, wherein the second host represented by Formula 2 is selected from the following compounds:

The organic light emitting diode of claim 1, wherein the light emitting layer comprises a first host and a second host: dopant in a volume ratio of 95: 5 to 70:30.

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