KR102138582B1 - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents

Abstract

The present invention is an organic light-emitting compound, characterized in that it is a compound represented by the following [Chemical Formula 1], and when it is employed in an organic layer of an organic electroluminescent device, it is capable of driving a low voltage as compared to conventional materials, and thus has excellent power efficiency. Compared to this, it is possible to provide a device having excellent light emission characteristics such as significantly improved luminance, light emission efficiency, and long life.
[Formula 1]

Description

Organic electroluminescent compound and an electroluminescent device comprising the same

The present invention relates to a novel organic light-emitting compound and an organic electroluminescent device capable of low-voltage driving and excellent luminance and life characteristics, including the same.

Materials used as the organic material layer in the organic light emitting device may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on their function. The light emitting materials include blue, green, and red light emitting materials, and yellow and orange light emitting materials necessary for realizing a better natural color depending on the light emitting color.

In addition, a host/dopant system may be used as a light emitting material in order to increase color purity and increase light emission efficiency through energy transfer. The principle is that when a small amount of a dopant having a smaller energy band gap and a higher luminous efficiency is mixed with a light emitting layer than a host mainly constituting the light emitting layer, excitons generated from the host are transported to the dopant to produce high efficiency light. At this time, since the wavelength of the host moves to the wavelength of the dopant, light of a desired wavelength can be obtained according to the type of dopant used.

However, in order to sufficiently exhibit the excellent characteristics of the above-described organic light-emitting device, materials constituting an organic material layer in the device, for example, a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc. Although it should be preceded by the support, the development of a stable and efficient organic material layer material for an organic light emitting device has not been sufficiently achieved, and therefore, the development of a new material continues to be required.

Accordingly, the present invention is to provide a novel organic light-emitting compound and an organic electroluminescent device having excellent light-emitting characteristics such as driving voltage, luminance, and lifetime by employing the same.

The present invention provides a novel organic light-emitting compound, characterized in that represented by the following [Formula 1] to solve the above problems.

[Formula 1]

In addition, the present invention provides an organic electroluminescent device having an anode, a cathode, an organic material layer interposed between the anode and the cathode, and comprising an organic light emitting compound represented by [Chemical Formula 1].

The specific substituents of the above [Formula 1] will be described later.

The organic electroluminescent device comprising the organic light-emitting compound according to the present invention is capable of low-voltage driving, and thus has excellent power efficiency, and has excellent light-emitting characteristics such as significantly improved luminance and long life compared to the prior art.

1 is a schematic diagram of an organic light emitting device according to an embodiment of the present invention.

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

The present invention is an organic light emitting compound capable of improving light emission characteristics such as power efficiency, brightness, and lifetime of an organic light emitting device, and is used as a dopant compound in a light emitting layer, and is a compound represented by the following [Formula 1] do.

[Formula 1]

In the above [Formula 1],

A may be a substituted or unsubstituted aryl group having 5 to 60 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 60 carbon atoms.

L is a substituted or unsubstituted C1 to C60 alkylene group, a substituted or unsubstituted C2 to C60 Alkenylene group, substituted or unsubstituted C2 to C60 alkynylene group, substituted or unsubstituted C3 to C60 Cycloalkylene group, substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, substituted or unsubstituted arylene group having 5 to 50 carbon atoms, substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms, substituted or unsubstituted A substituted or unsubstituted substituted or unsubstituted carbon atom having 1 to 60 carbon atoms of 3 to 30 substituted or unsubstituted arylene groups of 6 to 60 cycloalkyl having 3 to 30 carbon atoms and 1 or more substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms. It may be selected from a heteroarylene group of 60.

Ar is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, and a substituted or unsubstituted hetero atom, O, N , S or P may be selected from a heteroaryl group having 2 to 50 carbon atoms.

R ₁ to R ₈ are the same as or different from each other, and each independently hydrogen, deuterium, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 5 to 50 carbon atoms, substituted or unsubstituted Alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, substituted or Unsubstituted and heteroaryl O, N, S or P having 2 to 50 carbon atoms heteroaryl group, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, Substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, substituted or unsubstituted arylthiooxy group having 5 to 30 carbon atoms, substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, substituted or unsubstituted 5 to 5 carbon atoms 30 arylamine group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a cyano group, a nitro group and a halogen group.

In addition, R ₁ to R ₈ may combine with each other or adjacent substituents to form a saturated or unsaturated ring.

X and Y are the same or different from each other, and each independently CR ₃₁ R ₃₂ , NR ₃₃ , O, S, SiR ₃₄ R ₃₅ , GeR ₃₆ R ₃₇ , PR ₃₈ , PR ₃₉ (=O), C=O or BR _It may be ₄₀ , wherein R ₃₁ to R ₄₀ is the same as the definition of R ₁ to R ₈ .

n is an integer from 0 to 3, m is an integer from 1 to 4, and * of Q means a site to be bonded.

According to a preferred embodiment of the present invention, the A may be any one selected from the following [Formula A1] to [Formula A8].

[Formula A1] [Formula A2]

[Formula A3] [Formula A4]

[Formula A5] [Formula A6]

[Formula A7] [Formula A8]

In the above [Formula A1] to [Formula A8], the * means a binding site, and R ₁₁ to R ₂₆ are the same as the definitions of R ₁ to R ₈ in [Formula 1].

On the other hand, the aryl group, which is a substituent used in the present invention, is an organic radical derived from an aromatic hydrocarbon by one hydrogen removal, and includes a single or fused ring system containing 5 to 7 members, preferably 5 or 6 members, In addition, when there is a substituent in the aryl group, the adjacent substituents may be fused with each other to form a ring.

Specific examples of the aryl are phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-ethylphenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, 4-methylbiphenyl group, 4- Ethyl biphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, 1-naphthyl group, 2-naphthyl group, 1-methylnaphthyl group, 2-methylnaphthyl group, anthryl group, phenanthryl group, pyrene And aromatic groups such as nil group, indenyl, fluorenyl group, tetrahydronaphthyl group, pyrenyl, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl, and the like.

At least one hydrogen atom of the aryl group is a deuterium atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a silyl group, an amino group (-NH ₂ , -NH(R), -N(R')(R"), R 'And R'are each independently an alkyl group having 1 to 10 carbon atoms, in this case referred to as an "alkylamino group"), amidino group, hydrazine group, hydrazone group, carboxyl group, sulfonic acid group, phosphoric acid group, alkyl group having 1 to 24 carbon atoms, Halogenated alkyl group having 1 to 24 carbon atoms, alkenyl group having 1 to 24 carbon atoms, alkynyl group having 1 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 6 to 24 carbon atoms, carbon number It may be substituted with a heteroaryl group having 2 to 24 or a heteroarylalkyl group having 2 to 24 carbon atoms.

The heteroaryl group which is a substituent used in the present invention may be any one selected from the following [Structural Formula 1] to [Structural Formula 6].

[Structural Formula 1] [Structural Formula 2] [Structural Formula 3]

[Structural Formula 4] [Structural Formula 5] [Structural Formula 6]

In the above [Structural Formula 1] to [Structural Formula 6],

T ₁ to T ₈ are the same as or different from each other, and each independently, C(R ₄₁ ), C(R ₄₂ )(R ₄₃ ), N, N(R ₄₄ ), may be any one selected from O and S, , R ₃₁ to R ₄₄ are the same or different from each other, and each independently hydrogen, deuterium, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted It may be any one selected from an aryl group having 5 to 50 carbon atoms and a substituted or unsubstituted heteroaryl group having 2, 50 carbon atoms having O, N, or S as a hetero atom, and each of the above [Structural Formula 1] to [Structural Formula] 6] to R ₃₁ to R ₄₄ One of the above may be combined with nitrogen in [Formula 1] to form a single bond.

In addition, [Structural Formula 3] may include a compound represented by the following [Structural Formula 3-1] due to a resonance structure according to the movement of electrons.

[Structural Formula 3-1]

In [Structural Formula 3-1], T ₁ to T ₅ and R ₃₃ and R ₃₄ are the same as defined above.

Further, according to a preferred embodiment of the present invention, the above [Structural Formula 1] to [Structural Formula 6] may be selected from the following [Structural Formula 7].

[Structural Formula 7]

In the above [Formula 7],

X is hydrogen, deuterium, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 5 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon number 2 to 20 alkynyl groups, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl groups having 5 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted Aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, substituted or unsubstituted arylthiooxy group having 5 to 30 carbon atoms, substituted or unsubstituted alkyl having 1 to 30 carbon atoms Group consisting of amine group, substituted or unsubstituted aryl group having 5 to 5 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms having O, N, S and P, cyano group, nitro group, halogen group Any one selected from among, m is an integer from 1 to 11, and when m is 2 or more, a plurality of Xs are the same or different from each other, and any one of the one or more Xs is A, L, Q in the above Chemical Formula 1 , Ar and any one of these substituents to form a single bond.

Specific examples of the alkyl group which is a substituent used in the present invention are methyl group, ethyl group, propyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, iso-amyl group, hexyl group, heptyl group, octyl group, Stearyl groups, trichloromethyl groups, trifluoromethyl groups, and the like, and one or more hydrogen atoms of the alkyl groups include deuterium atoms, halogen atoms, hydroxy groups, nitro groups, cyano groups, trifluoromethyl groups, silyl groups (in this case, " Alkylsilyl group"), a substituted or unsubstituted amino group (-NH ₂ , -NH(R), -N(R')(R"), wherein R, R'and R" each independently represent 1 carbon atom. To an alkyl group of 24 to 24 (in this case, referred to as "alkylamino group"), amidino group, hydrazine group, hydrazone group, carboxyl group, sulfonic acid group, phosphoric acid group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, Alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 5 to 24 carbon atoms, arylalkyl group having 6 to 24 carbon atoms, heteroaryl group having 3 to 24 carbon atoms or carbon number It may be substituted with 3 to 24 heteroarylalkyl groups.

Specific examples of the alkoxy group which is a substituent used in the present invention include methoxy group, ethoxy group, propoxy group, isobutyloxy group, sec-butyloxy group, pentyloxy group, iso-amyloxy group, hexyloxy group and the like. It can be substituted with the same substituents as in the case of the alkyl group.

Specific examples of the halogen group which is a substituent used in the compound of the present invention include fluorine (F), chlorine (Cl), and bromine (Br).

The aryloxy group, which is a substituent used in the present invention, means an -O- aryl radical, wherein the aryl group is as defined above, and as a specific example, phenoxy, naphthoxy, anthracenyloxy, phenanthrenyloxy, fluorenyl Oxy, indenyloxy, and the like, and one or more hydrogen atoms contained in the aryloxy group can be further substituted.

Specific examples of the silyl group which is a substituent used in the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, silyl, diphenylvinylsilyl, methylcyclobutylsilyl And dimethylfurylsilyl.

Specific examples of the alkenyl group used in the present invention represent a straight or branched alkenyl group, 3-pentenyl group, 4-hexenyl group, 5-heptenyl group, 4-methyl-3-pentenyl group, 2,4 -Dimethyl-pentenyl group, 6-methyl-5-heptenyl group, 2,6-dimethyl-5-heptenyl group, etc. are mentioned.

In addition, in the present invention, the'substituted' in the'substituted or unsubstituted' is deuterium, cyano group, halogen group, hydroxy group, nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, Alkenyl group having 1 to 24 carbon atoms, alkynyl group having 1 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 6 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms or carbon number 2 to 24 heteroarylalkyl groups, 1 to 24 alkoxy groups, 1 to 24 alkylamino groups, 1 to 24 arylamino groups, 1 to 24 heteroarylamino groups, 1 to 24 alkylsilyl groups, It means that it is substituted with one or more substituents selected from the group consisting of arylsilyl groups having 1 to 24 carbon atoms, aryloxy groups having 1 to 24 carbon atoms, germanium, phosphorus and boron.

In addition, the carbon number range of the alkyl group or the aryl group in the above "substituted or unsubstituted alkyl group having 1 to 30 carbon atoms", "substituted or unsubstituted aryl group having 5 to 50 carbon atoms", etc., considers the part where the substituent is substituted It does not mean the total number of carbon atoms constituting the alkyl portion or the aryl portion when viewed as unsubstituted. For example, the phenyl group substituted with a butyl group in the para position means that it corresponds to an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

In addition, in the organic light emitting compound of [Formula 1] according to the present invention, A, L, Ar, R ₁ to R ₈ , R ₃₁ to R ₄₀ , X and Y are each independently substituted with one or more substituents May, the at least one substituent is deuterium, cyano group, halogen group, nitro group, hydroxy group, an alkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, 1 to 24 carbon atoms Alkylamino group, C1-C24 arylamino group, C1-C24 alkoxy group, C3-C24 cycloalkyl group, C6-C24 aryloxy group, C1-C24 alkylsilyl group and C6-C24 It may be selected from the group consisting of arylsilyl groups.

According to a more preferred embodiment of the present invention, [Chemical Formula 1] may be any one selected from compounds represented by the following [Chemical Formula 8] to [Chemical Formula 116].

[Formula 8] [Formula 9] [Formula 10] [Formula 11]

[Formula 12] [Formula 13] [Formula 14] [Formula 15]

[Formula 16] [Formula 17] [Formula 18] [Formula 19]

[Formula 20] [Formula 21] [Formula 22] [Formula 23]

[Formula 24] [Formula 25] [Formula 26] [Formula 27]

[Formula 28] [Formula 29] [Formula 30] [Formula 31]

[Formula 32] [Formula 33] [Formula 34] [Formula 35]

[Formula 36] [Formula 37] [Formula 38] [Formula 39]

[Formula 40] [Formula 41] [Formula 42] [Formula 43]

[Formula 44] [Formula 45] [Formula 46] [Formula 47]

[Formula 48] [Formula 49] [Formula 50] [Formula 51]

[Formula 52] [Formula 53] [Formula 54] [Formula 55]

[Formula 56] [Formula 57] [Formula 58] [Formula 59]

[Formula 60] [Formula 61] [Formula 62] [Formula 63]

[Formula 64] [Formula 65] [Formula 66] [Formula 67]

[Formula 68] [Formula 69] [Formula 70] [Formula 71]

[Formula 72] [Formula 73] [Formula 74] [Formula 75]

[Formula 76] [Formula 77] [Formula 78] [Formula 79]

[Formula 80] [Formula 81] [Formula 82] [Formula 83]

[Formula 84] [Formula 85] [Formula 86] [Formula 87]

[Formula 88] [Formula 89] [Formula 90] [Formula 91]

[Formula 92] [Formula 93] [Formula 94] [Formula 95]

[Formula 96] [Formula 97] [Formula 98] [Formula 99]

[Formula 100] [Formula 101] [Formula 102] [Formula 103]

[Formula 104] [Formula 105] [Formula 106] [Formula 107]

[Formula 108] [Formula 109] [Formula 110] [Formula 111]

[Formula 112] [Formula 113] [Formula 114] [Formula 115]

[Formula 116]

In addition, the present invention includes a first electrode, a second electrode opposed to the first electrode, and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer is represented by [Formula 1] One or more light-emitting compounds may be included.

In addition, the organic layer containing the organic light emitting compound of the present invention may include at least one of a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function simultaneously, a light emitting layer, an electron transport layer, and an electron injection layer have. At this time, the organic layer interposed between the first electrode and the second electrode may include a light emitting layer, the light emitting layer is made of a host and a dopant, the organic light emitting compound of [Formula 1] according to the present invention as a dopant Can be used.

Meanwhile, in the present invention, the light-emitting layer includes a host material together with a compound represented by [Chemical Formula 1] according to the present invention, and the content of the organic light-emitting compound according to the present invention in the light-emitting layer, that is, the dopant is usually about 100 wt. It can be selected from about 0.01 to about 20 parts by weight based on parts.

Meanwhile, in the present invention, as the electron transport layer material, a known electron transport material may be used as a function of stably transporting electrons injected from an electron injection electrode (Cathode). Examples of known electron transport materials include quinoline derivatives, in particular tris(8-quinolinorate)aluminum (Alq3), TAZ, Balq, beryllium bis(benzoquinolin-10-noate) (beryllium bis (benzoquinolin-10- It is also possible to use materials such as olate: Bebq2), ADN, [Compound 201], [Compound 202], and oxadiazole derivatives PBD, BMD, BND.

TAZ BAlq

[Compound 201] [Compound 202] BCP

Further, in the electron transport layer used in the present invention, the organometallic compound represented by the following [Chemical Formula C] may be used alone or in combination with the electron transport layer material.

[Chemical Formula C]

In the above [Formula C],

Y is a portion selected from C, N, O, and S directly bonded to M to form a single bond, and a portion selected from C, N, O, and S forming a coordination bond to M. And a ligand chelated by the single bond and coordination bond.

M is an alkali metal, alkaline earth metal, aluminum (Al) or boron (B) atom.

OA is a monovalent ligand capable of single bond or coordination with the M, wherein O is oxygen, and A is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, Substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 5 to 30 carbon atoms It is any one selected from an alkenyl group and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having O, N or S as a hetero atom.

In addition, m=1, n=0 when M is one metal selected from alkali metals, or m=1, n=1 when M is one metal selected from alkaline earth metals, or m =2, n=0, and when M is boron or aluminum, m = 1 to 3, n is any one of 0 to 2, and m + n = 3 is satisfied.

The'substituted' in the'substituted or unsubstituted' is deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group, alkoxy group, alkylamino group, arylamino group, hetero arylamino group, alkylsilyl group, arylsilyl group, It means substituted with one or more substituents selected from the group consisting of aryloxy group, aryl group, heteroaryl group, germanium, phosphorus and boron.

In addition, each of Y is the same or different, and may be any one selected from the following [Structural C1] to [Structural C39] independently of each other.

[Structural Formula C1] [Structural Formula C2] [Structural Formula C3]

[Structural C4] [Structural C5] [Structural C6]

[Structural C7] [Structural C8] [Structural C9] [Structural C10]

[Structural C11] [Structural C12] [Structural C13]

[Structural C14] [Structural C15] [Structural C16]

[Structural C17] [Structural C18] [Structural C19] [Structural C20]

[Structural C21] [Structural C22] [Structural C23]

[Structural C24] [Structural C25] [Structural C26]

[Structural C27] [Structural C28] [Structural C29] [Structural C30]

[Structural C31] [Structural C32] [Structural C33]

[Structural C34] [Structural C35] [Structural C36]

[Structural C37] [Structural C38] [Structural C39]

In the above [Structural Formula C1] to [Structural Formula C39],

R are the same or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted Heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or Unsubstituted alkylamino group having 1 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, and substituted or unsubstituted arylsilyl having 6 to 30 carbon atoms. It is selected from groups, and may be connected to adjacent substituents with alkylene or alkenylene to form a spiro ring or fused ring.

L is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted 5 to 30 carbon atoms Heteroaryl group and a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms, L is an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, 3 to 20 carbon atoms It is further substituted with one or more substituents selected from heteroaryl groups, cyano groups, halogen groups, deuterium, and hydrogen, and may be connected to adjacent substituents with alkylene or alkenylene to form a spiro ring or fused ring.

Hereinafter, the organic electroluminescent device of the present invention will be described with reference to FIG. 1.

1 is a cross-sectional view showing the structure of an organic light emitting device of the present invention. The organic light emitting device according to the present invention includes an anode 20, a hole transport layer 40, an organic light emitting layer 50, an electron transport layer 60 and a cathode 80, and a hole injection layer 30, if necessary The electron injection layer 70 may be further included, and in addition, an intermediate layer of one or two layers may be further formed, and a hole blocking layer or an electron blocking layer may be further formed.

Referring to FIG. 1, an organic electroluminescent device of the present invention and a manufacturing method thereof are as follows.

First, an anode 20 is formed by coating a material for the anode electrode on the substrate 10. Here, as the substrate 10, a substrate used in a conventional organic EL device is used, but an organic substrate or a transparent plastic substrate having excellent transparency, surface smoothness, handling ease, and waterproofness is preferable. In addition, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), and zinc oxide (ZnO) are used as the anode electrode material, which is transparent and has excellent conductivity.

A hole injection layer 30 is formed by vacuum-evaporating or spin coating a hole injection layer material on the anode 20 electrode. Next, a hole transport layer 40 is formed by vacuum thermally evaporating or spin coating the hole transport layer material on the hole injection layer 30.

The hole injection layer material can be used without particular limitation as long as it is commonly used in the art, for example, 2-TNATA[4,4',4"-tris(2-naphthylphenyl-phenylamino)-triphenylamine] , NPD[N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine)], TPD[N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'- biphenyl-4,4'-diamine],DNTPD[N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine ] Etc. can be used.

In addition, it is not particularly limited as long as it is commonly used in the art as a material for the hole transport layer, for example, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1 -Biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine (α-NPD) or the like can be used.

Subsequently, an organic light emitting layer 50 is stacked on the hole transport layer 40 and a hole blocking layer (not shown) is selectively deposited on the organic light emitting layer 50 to form a thin film as a vacuum deposition method or a spin coating method. can do. The hole blocking layer serves to prevent this problem by using a material with a very low level of HOMO (Highest Occupied Molecular Orbital) because the life and efficiency of the device is reduced when holes pass through the organic light emitting layer and enter the cathode. . At this time, the hole-blocking material used is not particularly limited, but has an electron transporting ability and has a higher ionization potential than the light emitting compound, and typically BAlq, BCP, TPBI, etc. can be used.

After the electron transport layer 60 is deposited on the hole blocking layer through a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed and a metal for forming a cathode is vacuum-coated on the electron injection layer 70. The organic EL device is completed by depositing to form the cathode 80 electrode. Here, the cathode forming metals include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver ( Mg-Ag) and the like, and a transmissive cathode using ITO and IZO can be used to obtain a front light emitting device.

In addition, the light emitting layer may include a host and a dopant compound represented by [Formula 1] according to the present invention, the thickness of the light emitting layer is preferably 50 to 2,000 Å.

At this time, the host used for the light emitting layer may be a compound represented by the following [Chemical Formula 1A] to [Chemical Formula 1D].

[Formula 1A]

In the above [Formula 1A],

Ar _{7 ,} Ar ₈ and Ar ₉ are the same or different from each other, and each independently, a single bond, a substituted or unsubstituted C ₅ -C ₆₀ aromatic linking group, or a substituted or unsubstituted C ₂ -C ₆₀ It may be a heteroaromatic linking group.

R ₂₁ to R ₃₀ are the same or different from each other, and each independently hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or Salts thereof, phosphoric acid or salts thereof, substituted or unsubstituted alkyl groups having 1 to 60 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 60 carbon atoms, substituted or unsubstituted alkynyl groups having 2 to 60 carbon atoms, substituted or unsubstituted Alkoxy group having 1 to 60 carbon atoms, substituted or unsubstituted alkylthio having 1 to 60 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, substituted or unsubstituted aryl having 6 to 60 carbon atoms Group, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a substituted or unsubstituted carbon number 1 to 60 (alkyl) amino groups, di (substituted or unsubstituted alkyl having 1 to 60 carbon atoms) amino group, or (substituted or unsubstituted aryl having 6 to 60 carbon atoms) amino group, di (substituted or unsubstituted carbon number 6 To 60 aryl) amino group, substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, may be selected from boron, each substituent Condensed rings may form with adjacent groups.

The e and f and g are the same or different from each other, and each independently an integer of 0 or 1 to 4.

The two sites indicated by * of the anthracene may be the same or different from each other, and each independently combine with the P or Q structure to form an anthracene-based derivative selected from [Chemical Formula 1Aa-1] to [Chemical Formula 1Aa-3]. can do.

[Formula 1Aa-1] [Formula 1Aa-2] [Formula 1Aa-3]

Here, the'substituted' in the'substituted or unsubstituted' is deuterium, cyano group, halogen group, hydroxy group, nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, 1 to 24 carbon atoms An alkenyl group, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, or a heterocycle having 2 to 24 carbon atoms Arylalkyl group, alkoxy group having 1 to 24 carbon atoms, alkylamino group having 1 to 24 carbon atoms, arylamino group having 1 to 24 carbon atoms, heteroaryl amino group having 1 to 24 carbon atoms, alkylsilyl group having 1 to 24 carbon atoms, carbon having 1 to 24 carbon atoms It means that it is substituted with one or more substituents selected from the group consisting of an arylsilyl group and an aryloxy group having 1 to 24 carbon atoms.

[Formula 1B]

In the above [Formula 1B],

Ar ₁₇ to Ar ₂₀ are the same as or different from each other, and each independently comprises the same substituents as defined in Ar ₇ to Ar ₈ in Formula 1A, and R ₆₀ to R ₆₃ are defined in R ₂₁ to R ₃₀ in Formula 1A. It consists of the same substituents as.

The w and ww are the same or different from each other, the x and xx are the same or different from each other, and the w+ww and x+xx values are the same or different from each other, and each independently is an integer of 0-3. In addition, y and yy are the same or different from each other, and z and zz are the same or different from each other, and y+yy to z+zz values are 2 or less, and are integers of 0 to 2, respectively.

[Formula 1C]

In the above [Formula 1C],

Ar ₂₁ to Ar ₂₄ are the same as or different from each other, and each independently consists of the same substituents as defined in Ar ₇ to Ar ₈ in Formula 1A, and R ₆₄ to R ₆₇ in R ₂₁ to R ₃₀ in Formula 1A It consists of the same substituents as defined.

In addition, ee to hh are the same or different from each other, and each independently an integer of 1 to 4, and ii to ll are the same or different from each other, and each independently an integer of 0 to 4.

[Formula 1D]

In the above [Formula 1D],

Ar ₂₅ to Ar ₂₇ are the same as or different from each other, and each independently consists of the same substituents as defined in Ar ₇ to Ar ₈ in Formula 1A, and R ₆₈ to R ₇₃ are the same as or different from each other, and each independently the formula It consists of the same substituents as defined in R ₂₁ to R ₃₀ of 1A, and each substituent can form a saturated or unsaturated cyclic structure between adjacent ones. In addition, the mm to ss are the same as or different from each other, and each independently an integer of 0 to 4.

More specifically, the host may be displayed as any one selected from the group represented by the following [Host 1] to [Host 56], but is not limited thereto.

[Host 1] [Host 2] [Host 3] [Host 4]

[Host 5] [Host 6] [Host 7] [Host 8]

[Host 9] [Host 10] [Host 11] [Host 12]

[Host 13] [Host 14] [Host 15] [Host 16]

[Host 17] [Host 18] [Host 19] [Host 20]

[Host 21] [Host 22] [Host 23] [Host 24]

[Host 25] [Host 26] [Host 27] [Host 28]

[Host 29] [Host 30] [Host 31] [Host 32]

[Host 33] [Host 34] [Host 35] [Host 36]

[Host 37] [Host 38] [Host 39] [Host 40]

[Host 41] [Host 42] [Host 43] [Host 44]

[Host 45] [Host 46] [Host 47] [Host 48]

[Host 49] [Host 50] [Host 51] [Host 52]

[Host 53] [Host 54] [Host 55] [Host 56]

In addition, one or more layers selected from the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer may be formed by a single molecule deposition method or a solution process, wherein the deposition method Means a method of forming a thin film by evaporating a material used as a material for forming each layer through heating or the like in a vacuum or low pressure state, and the solution process is used as a material for forming each layer. It refers to a method of mixing a substance with a solvent and forming a thin film through a method such as inkjet printing, roll to roll coating, screen printing, spray coating, dip coating, spin coating, and the like.

In addition, the organic light emitting device according to the present invention can be used in a device selected from a flat panel display device, a flexible display device, a single color or white flat panel lighting device, and a single color or white flexible lighting device.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are intended to illustrate the present invention in more detail, it will be apparent to those skilled in the art that the scope of the present invention is not limited thereby.

Synthesis Example 1. Synthesis of Formula 18

Synthesis Example 1-1. Synthesis of <1-a>

<1-a> was synthesized by the following reaction formula 1.

[Scheme 1]

<1-a>

To a 1 L round bottom flask purged with nitrogen at room temperature, 9-xanthone (50.0 g, 255 mmol) and 300 mL of toluene were added, and the mixture was cooled to 0° C. and stirred. Trimethylaluminum (300 mL, 2.0 M) was slowly added dropwise and stirred at 0° C. for about 30 minutes. The temperature was raised to room temperature and stirred for 14 hours. Upon completion of the reaction, after lowering to 0 degrees, 1 M hydrochloric acid was slowly added dropwise, stirred for 30 minutes, extracted with ethyl acetate, and then the organic layer was concentrated under reduced pressure to obtain <1-a> (51 g, 95%).

Synthesis Example 1-2. Synthesis of <1-b>

<1-b> was synthesized by the following scheme 2.

[Scheme 2]

<1-a> <1-b>

To a 1 L round bottom flask purged with nitrogen at room temperature, 410 mL of <1-a> (51 g, 243 mmol) obtained from [Scheme 1] and tetrahydrofuran are added. After cooling to -78°C, normal butyl lithium (182 mL, 1.6 M) was slowly added dropwise, stirred for 30 minutes and heated to room temperature. After stirring for 12 hours at room temperature, the mixture was cooled to -78°C and iodine (80 g, 315 mmol) was added. The temperature was raised to room temperature and stirred for 2 hours. When the reaction was completed, an aqueous sodium thiosulfate solution was added, extracted with ethyl acetate, and concentrated under reduced pressure to obtain <1-b> (60 g, 72%).

Synthesis Example 1-3. Synthesis of <1-c>

<1-c> was synthesized by the following scheme 3.

[Scheme 3]

<1-b> <1-c>

<1-b> (15.0 g, 44 mmol) and 4-tertiary-butylaniline (9.3 g, 62 mmol), tris (dibenzylidene acetone) obtained from [Scheme 2] in a 250 mL round bottom flask at room temperature. Dipalladium (0.8 g, 1 mmol), BINAP (0.56 g, 1 mmol) sodium tertiary butoxide (8.6 g, 89 mmol), toluene 150 mL was added and refluxed for 12 hours. After filtration through celite, purification was performed by column chromatography to obtain <1-c> (6.4 g, 40%).

Synthesis Example 1-4. Synthesis of <Formula 18>

<Formula 18> was synthesized by the following scheme 4.

[Scheme 4]

<1-c> <Formula 18>

<1-c> (6.4 g, 18 mmol) and 1,6-dibromopyrene (3 g, 8.3 mmol), palladium acetate (0.07 g, 0.3) obtained from [Scheme 3] in a 250 mL round bottom flask at room temperature. mmol), sodium tertiary butoxide (1.6 g, 17 mmol), and 65 mL of toluene were added, followed by heating. When it reaches 50 degrees, add tertiary butylphosphine (0.13 mL, 0.3 mmol) and reflux for 1 hour. After completion of the reaction, the mixture was filtered through celite, and recrystallized from dichloromethane and hexane to obtain <Formula 18> (3.2 g, 42%).

MS (MALDI-TOF): 912.47 m/z [M ⁺ ]

Synthesis Example 2. Synthesis of Formula 26

Synthesis Example 2-1. Synthesis of <2-a>

<2-a> was synthesized by the following Reaction Scheme 5.

[Scheme 5]

<2-a>

In the same synthesis method as in [Reaction Scheme 2], instead of <1-a>, thiansrene was reacted to obtain <2-a> (55 g, 71%).

Synthesis Example 2-2. Synthesis of <2-b>

<2-b> was synthesized by the following Reaction Scheme 6.

[Scheme 6]

<2-a> <2-b>

In the same synthesis method as in [Reaction Scheme 3], 4-isopropylaniline was substituted for <2-a> instead of <1-b> and 4-tertyl-butylaniline, and <2-b> (10.2 g, 67 %).

Synthesis Example 2-3. Synthesis of <Formula 26>

<Formula 26> was synthesized by the following Reaction Scheme 7.

[Scheme 7]

<2-b> <Formula 26>

In the same synthesis method as in [Reaction Scheme 4], <2-b> was reacted instead of <1-c> to obtain <Formula 26> (7 g, 65%).

MS (MALDI-TOF): 896.24 m/z [M ⁺ ]

Synthesis Example 3. Synthesis of Formula 32

Synthesis Example 3-1. Synthesis of <3-a>

<3-a> was synthesized by the following scheme 8.

[Scheme 8]

<1-b> <3-a>

In the same synthesis method as in [Reaction Scheme 3], 3-methylaniline was reacted instead of 4-tertiary-butylaniline to obtain <3-a> (10.0 g, 43%).

Synthesis Example 3-2. Synthesis of <Formula 32>

<Formula 32> was synthesized by Reaction Scheme 9 below.

[Scheme 9]

<3-a> <Formula 32>

In the same synthesis method as in [Reaction Scheme 4], <3-a> was reacted instead of <1-c> to obtain <Formula 32> (5.1 g, 71%).

MS (MALDI-TOF): 828.37 m/z [M ⁺ ]

Synthesis Example 4. Synthesis of Formula 37

Synthesis Example 4-1. Synthesis of <4-a>

<4-a> was synthesized by the following scheme 10.

[Scheme 10]

<1-a> <4-a>

To a 1 L round bottom flask purged with nitrogen at room temperature, 160 mL of <1-a> (20 g, 95 mmol) and tetrahydrofuran are added. After cooling to -78 °C, normal butyl lithium (71 mL, 114 mmol) was slowly added dropwise. After completion of the dropwise addition, the mixture was stirred for 30 minutes and heated to room temperature. After stirring for 12 hours at room temperature, the mixture was cooled to -78°C and isobromine (31.2 g, 124 mmol) was added. The temperature was raised to room temperature and stirred for 2 hours. When the reaction was completed, extraction was performed with ethyl acetate, followed by concentration under reduced pressure to obtain <4-a> (19.8 g, 82%).

Synthesis Example 4-2. Synthesis of <4-b>

<4-b> was synthesized by the following scheme 11.

[Scheme 11]

<4-a> <4-b>

In the same synthesis method as in [Scheme 2], <4-a> was reacted instead of <1-a> to obtain <4-b> (20.1 g, 68%).

Synthesis Example 4-3. Synthesis of <4-c>

<4-c> was synthesized by the following Reaction Scheme 12.

[Scheme 12]

<4-b> <4-c>

In the same synthesis method as in [Reaction Scheme 3], <4-b> was reacted instead of <1-b> to obtain <4-c> (14.8 g, 70%).

Synthesis Example 4-4. Synthesis of <Formula 37>

<Formula 37> was synthesized by the following scheme 13.

[Scheme 13]

<4-c> <Formula 37>

In the same synthesis method as in [Reaction Scheme 4], <4-c> was reacted instead of <1-c> to obtain <Formula 37> (4.6 g, 52%).

MS (MALDI-TOF): 996.56 m/z [M ⁺ ]

Synthesis Example 5. Synthesis of Formula 49

Synthesis Example 5-1. Synthesis of <5-a>

<5-a> was synthesized by the following scheme 14.

[Scheme 14]

<5-a>

In a 1 L round-bottom flask, add 2-bromo-9,9'-dimethylfluorene (40 g, 146 mmol) and 400 mL of tetrahydrofuran and cool to -78 °C under a nitrogen atmosphere. Normally butyl lithium (100 mL, 1.6 M) was slowly added dropwise to the cooled solution. After completion of dropwise addition, the temperature is maintained for 1 hour and a half, and trimethyl borate is added dropwise at the same temperature. After 2 and a half hours, the temperature is raised to room temperature. After completion of the reaction, 2 M hydrochloric acid was added to acidify, and then extracted with ethyl acetate, and the organic layer was anhydrous treated with magnesium sulfate and concentrated under reduced pressure. Recrystallization with hexane gave <5-a> (23.2 g, 66%).

Synthesis Example 5-2. Synthesis of <5-b>

<5-b> was synthesized by the following Reaction Scheme 15.

[Scheme 15]

<5-a> <5-b>

In a 250 mL round bottom flask methyl-2-bromobenzoate (25.1 g, 117 mmol), <5-a> (23.2 g, 97 mmol), tetrakistriphenylphosphine palladium (2.25 g, 2 mmol), Potassium carbonate (26.9 g, 195 mmol), dioxane 116 mL, toluene 116 mL and water 46 mL were added and refluxed. When the reaction was completed, the organic layer obtained by extraction with water and ethyl acetate was anhydrously treated with magnesium sulfate, concentrated under reduced pressure, and separated by column chromatography to obtain <5-b> (28.7 g, 90%).

Synthesis Example 5-3. Synthesis of <5-c>

<5-c> was synthesized by the following Reaction Scheme 16.

[Scheme 16]

<5-b> <5-c>

In a 500 mL round-bottom flask, add <5-b> (28.7 g, 87 mmol) and 287 mL of tetrahydrofuran and cool to 0 °C under a nitrogen atmosphere. Methyl magnesium bromide (1.6 M, 87.4 mL) was slowly added dropwise to the cooled solution. After completion of dropwise addition, stir for 1 hour at room temperature and then stir for 2 hours. After completion of the reaction, 0.2 M hydrochloric acid was added to acidify, and then the mixture was extracted with ethyl acetate, and the organic layer was anhydrously treated with magnesium sulfate and concentrated under reduced pressure. Separated by column chromatography to obtain <5-c> (19.7 g, 69%).

Synthesis Example 5-4. Synthesis of <5-d>

<5-d> was synthesized by the following scheme 17.

[Scheme 17]

<5-c> <5-d>

In a 500 mL round bottom flask, add <5-c> (23 g, 60 mmol), 1 mL of hydrochloric acid and 200 mL of acetic acid and heat stir at 60°C. After completion of the reaction, the resulting crystals were filtered and washed with water and hexane to obtain <5-d> (14.5 g, 67%).

Synthesis Example 5-5. Synthesis of <5-e>

<5-e> was synthesized by the following scheme 18.

[Reaction Scheme 18]

<5-d> <5-e>

In a 250 mL round-bottom flask, add <5-d> (14.5 g, 48 mmol) and 45 mL of dimethylformamide and cool to 0 °C under a nitrogen atmosphere. N-bromosuccinimide (16.6 g, 93 mmol) was dissolved in 72 mL of dimethylformamide and slowly added dropwise. After completion of dropwise addition, the mixture was stirred for 1 hour at room temperature. Stir at 140° C. for 30 minutes. After completion of the reaction, the resulting crystals are filtered and washed with water and hexane. Recrystallization using hexane and dichloromethane gave <5-e> (14 g, 64%).

Synthesis Example 5-6. Synthesis of <5-f>

<5-f> was synthesized by the following Reaction Scheme 19.

[Scheme 19]

<5-f>

In the same synthesis method as in [Scheme 2], phenoxatine was reacted instead of <1-a> to obtain <5-f> (36 g, 88%).

Synthesis Example 5-7. Synthesis of <5-g>

<5-g> was synthesized by the following scheme 20.

[Scheme 20]

<5-f> <5-g>

In the same synthesis method as [Scheme 3], <5-g> instead of <1-b> and 3,5-difluoroaniline instead of 4-tertiary-butylaniline were reacted to <5-g> (8.6 g, 58%).

Synthesis Example 5-8. Synthesis of <Formula 49>

<Formula 49> was synthesized by the following Reaction Scheme 21.

[Scheme 21]

<5-g> <5-e> <Formula 49>

In the same synthesis method as in [Reaction Scheme 4], <5-g> instead of <1-c> and <5-e> instead of 1,6-dibromopyrene are reacted to <Formula 49> (3.9 g, 50 %).

MS (MALDI-TOF): 960.25 m/z [M ⁺ ]

Synthesis Example 6. Synthesis of Formula 58

Synthesis Example 6-1. Synthesis of <6-a>

<6-a> was synthesized by the following scheme 22.

[Scheme 22]

<6-a>

In the same synthesis method as in [Scheme 15], 1-naphthylboronic acid was reacted instead of <5-a> to obtain <6-a> (40 g, 63%).

Synthesis Example 6-2. Synthesis of <6-b>

<6-b> was synthesized by the following scheme 23.

[Scheme 23]

<6-a> <6-b>

In the same synthesis method as in Scheme 16, <6-a> instead of <5-b> and phenylmagnesium bromide instead of methyl magnesium bromide were reacted to obtain <6-b> (23.4 g, 52%).

Synthesis Example 6-3. Synthesis of <6-c>

<6-c> was synthesized by the following Reaction Scheme 24.

[Scheme 24]

<6-b> <6-c>

In the same synthesis method as in Scheme 17, <6-c> was reacted instead of <5-c> to obtain <6-c> (13.8 g, 57%).

Synthesis Example 6-4. Synthesis of <6-d>

<6-d> was synthesized by the following Reaction Scheme 25.

[Reaction Scheme 25]

<6-c> <6-d>

In the same synthesis method as in [Scheme 18], <6-c> was reacted instead of <5-d> to obtain <6-d> (14.6 g, 89%).

Synthesis Example 6-5. Synthesis of <6-e>

<6-e> was synthesized by the following reaction formula 26.

[Scheme 26]

<1-b> <6-e>

In the same synthesis method as in [Reaction Scheme 3], 4-aminobenzonitrile was reacted instead of 4-tertiary-butylaniline to obtain <6-e> (12.6 g, 52%).

Synthesis Example 6-6. Synthesis of <Formula 58>

<Formula 58> was synthesized by the following Reaction Scheme 27.

[Scheme 27]

<6-e> <6-d> <Formula 58>

In the same synthesis method as in [Reaction Scheme 4], <6-e> instead of <1-c> and <6-d> instead of 1,6-dibromopyrene are reacted to give <Formula 58> (4.3 g, 63 %).

MS (MALDI-TOF): 1016.41 m/z [M ⁺ ]

Synthesis Example 7. Synthesis of Formula 72

Synthesis Example 7-1. Synthesis of <7-a>

<7-a> was synthesized by the following scheme 28.

[Scheme 28]

<7-a>

In the same synthesis method as in [Scheme 15], <7-a> (58 g, 69%) was obtained by reacting 9-phenanthrylboronic acid instead of <5-a>.

Synthesis Example 7-2. Synthesis of <7-b>

<7-b> was synthesized by the following Reaction Scheme 29.

[Scheme 29]

<7-a> <7-b>

In the same synthesis method as in [Scheme 16], <7-a> instead of <5-b> and phenylmagnesium bromide instead of methyl magnesium bromide were reacted to obtain <7-b> (62.4 g, 84%).

Synthesis Example 7-3. Synthesis of <7-c>

<7-c> was synthesized by the following scheme 30.

[Scheme 30]

<7-b> <7-c>

In the same synthesis method as in [Scheme 17], <7-b> was reacted instead of <5-c> to obtain <7-c> (26.7 g, 50%).

Synthesis Example 7-4. Synthesis of <7-d>

<7-d> was synthesized by the following Reaction Scheme 31.

[Scheme 31]

<7-c> <7-d>

In the same synthesis method as in [Scheme 18], <7-c> was reacted instead of <5-d> to obtain <7-d> (10.2 g, 53%).

Synthesis Example 7-5. Synthesis of <7-e>

<7-e> was synthesized by the following scheme 32.

[Scheme 32]

<7-e>

In the same synthesis method as in [Scheme 1], 2-aminoanthraquinone was reacted instead of 9-xanthone to obtain <7-e> (18.4 g, 82%).

Synthesis Example 7-6. Synthesis of <7-f>

<7-f> was synthesized by the following scheme 32.

[Scheme 32]

<7-f>

In the same synthesis method as in Scheme 1, 2-thioxanthone was reacted instead of 9-xanthone to obtain <7-f> (10.8 g, 75%).

Synthesis Example 7-7. Synthesis of <7-g>

<7-g> was synthesized by the following scheme 33.

[Reaction Scheme 33]

<7-f> <7-g>

In the same synthesis method as in [Scheme 2], <7-f> was reacted instead of <1-a> to obtain <7-g> (15.4 g, 68%).

Synthesis Example 7-8. Synthesis of <7-h>

<7-h> was synthesized by the following scheme 34.

[Scheme 34]

<7-g> <7-e> <7-h>

In the same synthesis method as in [Reaction Scheme 3], <7-h> (10.4 g, 65) was reacted by <7-g> instead of <1-b> and <7-e> instead of 4-tertiary-butylaniline. %).

Synthesis Example 7-9. Synthesis of <Formula 72>

<Formula 72> was synthesized by the following Reaction Scheme 35.

[Scheme 35]

<7-h> <7-d> <Formula 72>

In the same synthesis method as in [Reaction Scheme 4], <7-h> instead of <1-c> and <7-d> instead of 1,6-dibromopyrene are reacted to <Formula 72> (6.6 g, 63 %).

MS (MALDI-TOF): 1365.61 m/z [M ⁺ ]

Synthesis Example 8. Synthesis of Formula 87

Synthesis Example 8-1. Synthesis of <8-a>

<8-a> was synthesized by the following scheme 36.

[Scheme 36]

<5-f> <8-a>

In the same synthesis method as in [Reaction Scheme 3], <5-f> was reacted instead of <1-b> to obtain <8-a> (11.9 g, 63%).

Synthesis Example 8-2. Synthesis of <Formula 87>

<Formula 87> was synthesized by the following scheme 37.

[Scheme 37]

<8-a> <Formula 87>

In the same synthesis method as in [Reaction Scheme 4], <8-a> instead of <1-c> and 6,12-dibromocricene instead of 1,6-dibromopyrene were reacted to give <Formula 87> (2.7 g, 32%).

MS (MALDI-TOF): 918.33 m/z [M ⁺ ]

Synthesis Example 9. Synthesis of Formula 95

Synthesis Example 9-1. Synthesis of <9-a>

<9-a> was synthesized by the following scheme 38.

[Scheme 38]

<9-a>

To a 1 L round bottom flask purged with nitrogen at room temperature, 350 mL of bromobenzene (35 g, 220 mmol) and tetrahydrofuran were added, and the mixture was cooled to -78°C and stirred. Normally butyl lithium (127 mL, 1.6 M) was slowly added dropwise, followed by stirring at the same temperature for about 1 hour. After adding 2,6-dibromoanthraquinone (30 g, 82 mmol) at the same temperature, the mixture was heated to room temperature and stirred for 4 hours. After the reaction was completed, ethyl acetate and distilled water were added to separate the layers. The organic layer was concentrated under reduced pressure to filter crystals with hexane. In a 500 mL round-bottom flask, add 300 mL of crystal, potassium iodo (39.1 g, 245 mmol), sodium hypochlorite (51.8 g, 489 mmol), acetic acid and reflux. After completion of the reaction, add water, cool, and filter. The filtered solid was dissolved in toluene and recrystallized to obtain <9-a> (26.4 g, 66%).

Synthesis Example 9-2. Synthesis of <9-b>

<9-b> was synthesized by the following scheme 39.

[Scheme 39]

<9-b>

In the same synthesis method as in [Scheme 1], 1-aminoanthraquinone was reacted instead of 9-xanthone to obtain <9-b> (19.2 g, 82%).

Synthesis Example 9-3. Synthesis of <9-c>

<9-c> was synthesized by the following scheme 40.

[Reaction Scheme 40]

<9-b> <9-c>

In the same synthesis method as in [Reaction Scheme 3], <9-c> (9.2 g, 55) was reacted by reacting <9-b> instead of 3-bromobiphenyl and 4-tertiary-butylaniline in place of <1-b>. %).

Synthesis Example 9-4. Synthesis of <Formula 95>

<Formula 95> was synthesized by the following Reaction Scheme 41.

[Scheme 41]

<9-c> <9-a> <Formula 95>

In the same synthesis method as in [Reaction Scheme 4], <9-c> instead of <1-c> and <9-a> instead of 1,6-dibromopyrene are reacted to <Formula 95> (4.1 g, 57 %).

MS (MALDI-TOF): 1132.57 m/z [M ⁺ ]

Examples 1 to 9: Preparation of organic light emitting diode

The ITO glass was patterned to have a light emitting area of 2 mm×2 mm and then washed. After mounting the substrate in a vacuum chamber, the base pressure was 1 × 10 ^-6 torr, and then the organic material was prepared on the ITO by DNTPD (700 kPa), α-NPD (300 kPa), BH1 as a host for the light emitting layer and produced by the present invention. Compounds (3 wt%) of Synthesis Examples 1 to 9 were co-deposited (300 kPa), and then deposited in the order of Alq ₃ (350 kPa), LiF (5 kPa), Al (1,000 kPa), and measured at 0.4 mA. .

[DNTPD] [α-NPD]

[BH1] [Alq ₃ ]

Comparative Examples 1 to 2

The organic light emitting devices for Comparative Examples 1 to 2 were manufactured in the same manner except that the following [Compound 101] and [Compound 102] were used instead of the compounds prepared by the invention in the device structures of Examples 1 to 9 above. The structure is as follows.

[Compound 101] [Compound 102]

For the organic light-emitting devices manufactured according to Examples 1 to 9 and Comparative Examples 1 to 2, voltage, luminance, color coordinates, and life were measured, and the results are shown in Table 1 below. T ₈₀ means the time required for the luminance to decrease from the initial luminance (5000 nits) to 80%.

division Host Dopant Voltage (V) Luminance (Cd/㎡) CIEx CIEy T ₈₀ Example 1 BH1 Compound 18 3.8 883 0.136 0.109 58 Example 2 BH1 Compound 26 3.8 713 0.137 0.118 62 Example 3 BH1 Compound 32 3.8 718 0.138 0.125 60 Example 4 BH1 Compound 37 3.8 793 0.141 0.111 60 Example 5 BH1 Compound 49 3.9 851 0.142 0.104 61 Example 6 BH1 Compound 58 3.8 729 0.143 0.105 59 Example 7 BH1 Compound 72 3.7 742 0.137 0.112 62 Example 8 BH1 Compound 87 3.8 736 0.137 0.103 59 Example 9 BH1 Compound 95 3.8 774 0.139 0.115 60 Comparative Example 1 BH1 Compound 101 6.4 515 0.149 0.166 46 Comparative Example 2 BH1 Compound 102 6.0 651 0.175 0.225 54

Claims (9)

The organic light emitting compound represented by the following [Formula 1]:
[Formula 1]

In the above [Formula 1],
A is any one selected from the following [Formula A1] to [Formula A8],
[Formula A1] [Formula A2]

[Formula A3] [Formula A4]

[Formula A5] [Formula A6]

[Formula A7] [Formula A8]

In the above [Formula A1] to [Formula A8], * means a site to bind,
L is a single bond or is selected from a substituted or unsubstituted arylene group having 6 to 50 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms,
Ar is different from Q, and is selected from a substituted or unsubstituted aryl group having 6 to 50 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having O, N, S or P heteroatoms,
R ₁ to R ₈ are the same as or different from each other, and each independently hydrogen, deuterium, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 5 to 50 carbon atoms, substituted or unsubstituted Alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, substituted or Heteroaryl group having 2 to 50 carbon atoms having O, N, S or P unsubstituted and heterogeneous, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms , Cyano group, nitro group and halogen group, and may combine with each other or adjacent substituents to form a saturated or unsaturated ring (however, each of R ₁ to R ₈ is different from Q),
X and Y are the same or different from each other, and each independently CR ₃₁ R ₃₂ , NR ₃₃ , O, S, SiR ₃₄ R ₃₅ , GeR ₃₆ R ₃₇ , PR ₃₈ , PR ₃₉ (=O), C=O or BR ₄₀ ,
R ₁₁ to R ₂₆ and R ₃₁ to R ₄₀ are the same as the definitions of R ₁ to R ₈ , respectively,
n is an integer from 0 to 3, m is an integer from 2, and * in Q means a site to be bonded. According to claim 1,
The R ₁ to R ₈ is an organic light-emitting compound, characterized in that to form a saturated or unsaturated ring by combining with each other or adjacent substituents. delete According to claim 1,
The A, L, Ar, R ₁ to R ₈ , R ₁₁ to R ₂₆ , R ₃₁ to R ₄₀ , X and Y are each independently deuterium, cyano group, halogen group, nitro group, hydroxy group, 1 to 24 carbon atoms Alkyl group, aryl group having 6 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, alkylamino group having 1 to 24 carbon atoms, arylamino group having 1 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms , C6-C24 aryloxy group, C1-C24 alkylsilyl group and C6-C24 arylsilyl group is further substituted with one or more substituents selected from the group consisting of organic light-emitting compounds. According to claim 1,
[Formula 1] is an organic light-emitting compound, characterized in that any one selected from compounds represented by the following formula:

[Formula 8] [Formula 9] [Formula 10] [Formula 11]

[Formula 12] [Formula 13] [Formula 14] [Formula 15]

[Formula 16] [Formula 17] [Formula 18] [Formula 19]

[Formula 20] [Formula 21] [Formula 22] [Formula 23]

[Formula 24] [Formula 25] [Formula 26] [Formula 27]

[Formula 28] [Formula 29] [Formula 30] [Formula 31]

[Formula 32] [Formula 33] [Formula 34] [Formula 35]

[Formula 36] [Formula 37] [Formula 38] [Formula 39]

[Formula 40] [Formula 41] [Formula 42] [Formula 43]

[Formula 44] [Formula 45] [Formula 46] [Formula 47]

[Formula 48] [Formula 49] [Formula 50] [Formula 51]

[Formula 52] [Formula 53] [Formula 54] [Formula 55]

[Formula 56] [Formula 57] [Formula 58] [Formula 59]

[Formula 60] [Formula 61] [Formula 62] [Formula 63]

[Formula 64] [Formula 65] [Formula 66] [Formula 67]

[Formula 68] [Formula 69] [Formula 70] [Formula 71]

[Formula 72] [Formula 73] [Formula 74] [Formula 75]

[Formula 76] [Formula 77] [Formula 78] [Formula 79]

[Formula 80] [Formula 81] [Formula 82] [Formula 83]

[Formula 84] [Formula 85] [Formula 86] [Formula 87]

[Formula 88] [Formula 89] [Formula 90] [Formula 91]

[Formula 92] [Formula 93] [Formula 94] [Formula 95]

[Formula 96] [Formula 97] [Formula 98] [Formula 99]

[Formula 100] [Formula 101] [Formula 102] [Formula 103]

[Formula 104] [Formula 105] [Formula 106] [Formula 107]

[Formula 112] [Formula 113] [Formula 114] [Formula 115]

[Formula 116] A first electrode; A second electrode opposed to the first electrode; And an organic layer interposed between the first electrode and the second electrode.
An organic electroluminescent device characterized in that the organic layer comprises at least one organic light emitting compound represented by [Chemical Formula 1] according to claim 1. The method of claim 6,
The organic layer comprises at least one of a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function simultaneously, a light emitting layer, an electron transport layer, and an electron injection layer. The method of claim 6,
The organic layer interposed between the first electrode and the second electrode includes a light emitting layer, the light emitting layer is made of a host and a dopant, and the organic light emitting compound represented by [Formula 1] is used as a dopant Organic electroluminescent device. The method of claim 6,
The organic light emitting device is an organic light emitting device characterized in that it is used in a device selected from a flat panel display device, a flexible display device, a monochrome or white flat lighting device and a monochrome or white flexible lighting device.

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