KR102121581B1 - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same, the organic electroluminescent compound according to the present invention has excellent thermal stability, high hole and electron transport ability, as well as high power efficiency and driving voltage characteristics. It has an excellent effect that no problem of concentration quenching due to steric hindrance and molecular association occurs.

Description

An organic electroluminescent compound and an electroluminescent device comprising the same

The present invention relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same.

Recently, an organic light emitting device capable of driving a low voltage with a self-emission type has superior viewing angle, contrast ratio, and no backlight, and is lightweight and thin, and consumes less than liquid crystal displays (LCDs), which are the mainstream of flat panel display devices. It is also advantageous in terms of power and has a wide range of color reproduction, attracting attention as a next-generation display device.

Organic light emitting diodes (OLEDs) are devices that emit light while extinguishing after pairing electrons and holes when a charge is injected into an organic light emitting layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode) to be.

An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic electroluminescent device, the organic material layer is often composed of a multi-layer structure composed of different materials, for example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. . When a voltage is applied between two electrodes in the structure of the organic electroluminescent device, holes are injected at the anode and electrons are injected at the cathode, and excitons are formed when the injected holes meet the electrons. When it falls to the ground again, it glows.

The organic electroluminescent device can not only form the device on a flexible transparent substrate such as plastic, but can also operate at a voltage lower than 10 V compared to a plasma display panel or an inorganic electroluminescent display. It has the advantages of relatively low power consumption and excellent color. In addition, the organic light emitting device can display three colors of green, blue, and red, and is a subject of much interest as a next-generation rich color display device.

In order for the organic electroluminescent device to sufficiently exhibit the above-described excellent characteristics, materials constituting an organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, are supported by stable and efficient materials. It should be preceded, but the development of a stable and efficient organic material layer material for an organic light emitting device has not been sufficiently achieved. Therefore, the development of new materials having low voltage driving, high efficiency and long life is continuously required in the art.

In order to solve the above problems, the present invention has excellent thermal stability, high hole and electron transport capability, and excellent power efficiency and driving voltage characteristics, resulting in short-term (eg, over 100 hours) pixel short-circuit when applying electric fields. An object of the present invention is to provide an organic electroluminescent compound in which no defect problem occurs.

In addition, there is no problem of crystallization, and uniformity of luminescence at high temperatures can be ensured, and solubility can be expressed by 3% or more with respect to the solvent without the use of a separate thickener. It is intended to provide an organic electroluminescent compound capable of forming.

In addition, it is intended to provide an organic thin film layer for an organic electroluminescent device comprising such an organic electroluminescent compound and an organic electroluminescent device comprising the same.

In order to solve the above problems, the present invention provides an organic electroluminescent compound of the following [Formula 1] or [Formula 2].

The definition of each substituent or skeleton atom will be described later.

[Formula 1]

[Formula 2]

In addition, the present invention provides an organic thin film layer for an organic light emitting device comprising at least one organic light emitting compound embodied in [Formula 1] or [Formula 2] and an organic electroluminescent device comprising the same.

The organic electroluminescent compound according to the present invention has excellent thermal stability, high hole and electron transport capability, as well as excellent power efficiency and driving voltage characteristics, resulting in short circuits during long-term (eg, over 100 hours) electric field application. It was confirmed that no problem of pixel defects caused by.

In addition, the organic electroluminescent compound according to some embodiments of the present invention does not cause any crystallization problems, and it is possible to secure luminescence uniformity at high temperatures, and solubility in a solvent without using a separate thickener. It was confirmed that film formation by the solution coating method was possible because more than% can be expressed.

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

One aspect of the present invention relates to an organic electroluminescent compound represented by the following [Formula 1] or [Formula 2].

[Formula 1]

[Formula 2]

In the above [Formula 1] to [Formula 2],

R ₁ to R ₆ are the same or different from each other, and each substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, substituted or unsubstituted aryl group having 6 to 60 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 60 carbon atoms. , Substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, substituted or unsubstituted 6 to 30 carbon atoms Arylamino group, substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, substituted or unsubstituted arylalkylamino group having 1 to 50 carbon atoms, substituted or unsubstituted Alkenyl group having 2 to 60 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, hydroxyl group, nitro group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or Salts thereof, substituted or unsubstituted cycloalkyl groups having 3 to 60 carbon atoms, substituted or unsubstituted aryloxy groups having 5 to 60 carbon atoms, substituted or unsubstituted arylthio groups having 5 to 60 carbon atoms, cyano groups, halogen groups, Selected from the group consisting of small and medium water and hydrogen, wherein R ₁ to R ₆ At least one of them is a heteroaryl group containing nitrogen.

In addition, the substituents of R ₁ to R ₆ are each independently a hydrogen atom, deuterium atom, halogen atom, hydroxyl group, cyano group, nitro group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or the like Salt, phosphoric acid or a salt thereof, an alkyl group having 1 to 60 carbon atoms, an alkenyl group having 2 to 60 carbon atoms, an alkynyl group having 2 to 60 carbon atoms, an alkoxy group having 1 to 60 carbon atoms, a cycloalkyl group having 3 to 60 carbon atoms, 6 to 60 carbon atoms Is an aryl group, an aryloxy group having 6 to 60 carbon atoms, an arylthio group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms, or -SiRRR or -NRR (wherein R may be the same or different from each other, respectively) Independently hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms).

L is a single bond, substituted or unsubstituted alkylene having 1 to 60 carbon atoms, substituted or unsubstituted alkenylene having 2 to 60 carbon atoms, substituted or unsubstituted alkynylene having 2 to 60 carbon atoms, substituted or unsubstituted Heterocycloalkylene having 2 to 6 carbon atoms including one or more selected from cycloalkylene having 3 to 60 carbon atoms, N, O and S, substituted or unsubstituted arylene having 6 to 50 carbon atoms and substituted or unsubstituted carbon number It is a divalent linking group selected from 3 to 50 heteroarylene.

m or n is an integer from 0 to 4, and when m or n is 2 or more, a plurality of Ls may be the same or different, respectively.

X ₁ and X ₂ are CRR, and the two Rs are the same or different from each other, and each independently hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms. to be.

In (CR ₂ ) _n of [Formula 2], n is an integer of 3 to 6, and R ₂ is each independently hydrogen, deuterium, or an alkyl group having 1 to 10 carbon atoms.

Further, with respect to Y, n is an integer from 0 to 1, and when n is 1, Y is selected from CRR, O and S, and each R is independently hydrogen, deuterium, or an alkyl group having 1 to 10 carbon atoms, It is a C6-C60 aryl group or a C2-C60 heteroaryl group.

According to a preferred embodiment of the present invention, L may be any one selected from the following [Structural C1] to [Structural C14].

[Structural C1] [Structural C2] [Structural C3] [Structural C4]

[Structural C5] [Structural C6] [Structural C7] [Structural C8] [Structural C9]

[Structural C10] [Structural C11] [Structural C12] [Structural C13] [Structural C14]

In the above [Structural Formula C1] to [Structural Formula C14],

Hydrogen or deuterium may be attached to the carbon site of the ring in each structural formula, and R is the same as the definition of R ₁ to R ₆ in [Formula 1] or [Formula 2].

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

Specific examples of the aryl group 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, And aromatic groups such as pyrenyl 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.

Meanwhile, the heteroaryl group included in the organic light emitting compound according to the present invention may be any one selected from the following [Structural Formula 1] to [Structural Formula 10].

[Structural Formula 1] [Structural Formula 2] [Structural Formula 3] [Structural Formula 4]

[Structural Formula 5] [Structural Formula 6] [Structural Formula 7]

[Structural Formula 8] [Structural Formula 9] [Structural Formula 10]

In the above [Structural Formula 1] to [Structural Formula 10],

T ₁ to T ₁₂ are the same as or different from each other, and each independently, selected from C(R ₄₁ ), C(R ₄₂ )(R ₄₃ ), N, N(R ₄₄ ), O and S, wherein R ₄₁ To R ₄₄ 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 cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted 5 to 5 carbon atoms 30 aryl group and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms having O, N, S or P as a hetero atom.

More preferably, [Structural Formula 1] to [Structural Formula 10] may be any one selected from the following [Structural Formula 11].

[Structural Formula 11]

In the above [Formula 11],

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 Choose from an amine group, a substituted or unsubstituted aryl group having 5 to 5 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms having O, N, S or P, cyano group, nitro group and halogen group And 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.

Specific examples of the alkyl group which is a substituent used in the present invention are methyl group, ethyl group, propyl group, isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, iso-amyl group, hexyl group, heptyl group , Octyl group, stearyl group, trichloromethyl group, trifluoromethyl group, and the like, and one or more hydrogen atoms of the alkyl group are deuterium atom, halogen atom, hydroxy group, nitro group, cyano group, trifluoromethyl group, silyl group. (In this case referred to as "alkylsilyl group"), a substituted or unsubstituted amino group (-NH ₂ , -NH(R), -N(R')(R"), where R, R'and R" are each Independently an alkyl group having 1 to 24 carbon atoms (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, carbon number having 1 to 24 carbon atoms Halogenated alkyl group, 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, hetero group having 3 to 24 carbon atoms It may be substituted with an aryl group or a heteroaryl alkyl group having 3 to 24 carbon atoms.

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, diphenylvinylsilyl, methylcyclobutylsilyl, dimethyl And furylsilyl.

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.

The organic electroluminescent compound represented by [Chemical Formula 1] or [Chemical Formula 2] according to the present invention is not limited in scope in the following specific compounds, and more specifically, among the compounds represented by [Chemical Formula 3] to [Chemical Formula 245] It may be selected.

The organic electroluminescent compound represented by [Chemical Formula 1] or [Chemical Formula 2] according to the present invention is not limited in scope in the following specific compounds, and more specifically, among the compounds represented by [Chemical Formula 3] to [Chemical Formula 245] It may be selected.

[Formula 3] [Formula 4] [Formula 5] [Formula 6]

[Formula 7] [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] [Formula 117] [Formula 118]

[화학식 119] [화학식 120] [화학식 121] [화학식 122]

[Formula 119] [Formula 120] [Formula 121] [Formula 122]

[Formula 123] [Formula 124] [Formula 125] [Formula 126]

[Chemical Formula 127] [Chemical Formula 128] [Chemical Formula 129] [Chemical Formula 130]

[Chemical Formula 131] [Chemical Formula 132] [Chemical Formula 133] [Chemical Formula 134]

[Formula 135] [Formula 136] [Formula 137] [Formula 138]

[Formula 139] [Formula 140] [Formula 141] [Formula 142]

[Formula 143] [Formula 144] [Formula 145] [Formula 146]

[Formula 147] [Formula 148] [Formula 149] [Formula 150]

[Chemical Formula 151] [Chemical Formula 152] [Chemical Formula 153] [Chemical Formula 154]

[Formula 155] [Formula 156] [Formula 157] [Formula 158]

[Formula 159] [Formula 160] [Formula 161] [Formula 162]

[Formula 163] [Formula 164] [Formula 165] [Formula 166]

[Chemical Formula 167] [Chemical Formula 168] [Chemical Formula 169] [Chemical Formula 170]

[Formula 171] [Formula 172] [Formula 173] [Formula 174]

[Formula 175] [Formula 176] [Formula 177] [Formula 178]

[Formula 179] [Formula 180] [Formula 181] [Formula 182]

[Formula 183] [Formula 184] [Formula 185] [Formula 186]

[Formula 187] [Formula 188] [Formula 189] [Formula 190]

[Formula 191] [Formula 192] [Formula 193] [Formula 194]

[Formula 195] [Formula 196] [Formula 197] [Formula 198]

[Formula 199] [Formula 200] [Formula 201] [Formula 202]

[Formula 203] [Formula 204] [Formula 205] [Formula 206]

[Formula 207] [Formula 208] [Formula 209] [Formula 210]

[Formula 211] [Formula 212] [Formula 213] [Formula 214]

[Formula 215] [Formula 216] [Formula 217] [Formula 218]

[Formula 219] [Formula 220] [Formula 221] [Formula 222]

[화학식 223] [화학식 224] [화학식 225] [화학식 226]

[Formula 223] [Formula 224] [Formula 225] [Formula 226]

[Formula 227] [Formula 228] [Formula 229] [Formula 230]

[Formula 231] [Formula 232] [Formula 233] [Formula 234]

[Formula 235] [Formula 236] [Formula 237] [Formula 238]

[Formula 239] [Formula 240] [Formula 240] [Formula 241]

[화학식 243] [화학식 244] [화학식 245]

[Formula 243] [Formula 244] [Formula 245]

Another aspect of the present invention relates to an organic thin film layer for an organic light emitting device comprising at least one compound according to [Formula 1] to [Formula 2] according to various embodiments of the present invention.

According to one embodiment of the present invention, the organic thin film layer is characterized in that it further comprises at least one compound represented by the following [Formula A-1] to [Formula J-1].

[General Formula A-1]

ML ₁ L ₂ L ₃

The M is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15, and 16, preferably Ir, Pt, Pd, Rh, Re , Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au and Ag. In addition, the L ₁ , L ₂ and L ₃ are the same as or different from each other as a ligand, and each independently selected from the following [Structural D], but is not limited thereto. In addition, * in the following structural formula D represents a site that binds to the metal ion M.

[Structural Formula D]

In the above [Formula D],

R is different from or the same as 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 50 carbon atoms, substituted or unsubstituted Heteroaryl group having 5 to 50 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 may be any one selected from groups.

R is independently selected from alkyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, aryl groups having 6 to 40 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, cyano groups, halogen groups, deuterium, and hydrogen. It may be further substituted with one or more substituents.

In addition, R may be connected to each adjacent substituent by alkylene or alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring.

The L may be connected to an adjacent substituent by alkylene or alkenylene to form a spiro ring or fused ring.

As a specific example, the dopant represented by [General Formula A-1] may be any one selected from the following compounds, but is not limited thereto.

[General Formula B-1]

In the above [General Formula B-1],

M ^A1 represents the same metal ion as defined in [General Formula A-1], and also Y ^A11 , Y ^A14 , Y ^A15 and Y ^A18 Each independently represents a carbon atom or a nitrogen atom, Y ^A12 , Y ^A13 , Y ^A16 and Y ^A17 each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, oxygen atom, or sulfur atom, L ^A11 , L ^A12 , L ^A13 , and L ^A14 each represent a linking group as previously defined, and Q ^A11 , Q ^A12 represent a partial structure containing an atom that binds to M ^A1 .

The exemplary structure of the compound represented by [General Formula B-1] is as follows, but is not limited thereto.

[General Formula C-1]

In the above [General Formula C-1],

M ^B1 represents the same metal ion as defined in [General Formula A-1], Y ^B11 , Y ^B14 , Y ^B15 and Y ^B18 each independently represent a carbon atom or a nitrogen atom, Y ^B12 , Y ^B13 , Y ^B16 And Y ^B17 each independently represents a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom, and a sulfur atom, L ^B11 , L ^B12 , L ^B13 , and L ^B14 represent a linking group, and Q ^B11 , Q ^B12 are It shows the partial structure containing the atom couple|bonded with M ^B1 .

The exemplary structure of the compound represented by [General Formula C-1] is as follows, but is not limited thereto.

[General Formula D-1]

In the above [General Formula D-1],

M ^C1 represents a metal ion as the same metal ion as defined in [General Formula A-1], and R ^C11 and R ^C12 are each independently a hydrogen atom, a substituent that connects to each other, and forms a 5-membered ring. Represents a substituent, R ^C13 , R ^C14 each independently represents a hydrogen atom, a substituent that connects to each other to form a 5-membered ring, or a substituent that does not have anything to connect to each other, G ^C11 , G ^C12 each independently represents a nitrogen atom, a substitution Or represents an unsubstituted carbon atom, L ^C11 , L ^C12 represents a linking group, and Q ^C11 , Q ^C12 represents a partial structure containing an atom bound to M ^C1 .

The exemplary structure of the compound represented by [General Formula D-1] is as follows, but is not limited thereto.

[General Formula E-1]

In the above [General Formula E-1],

M ^D1 represents the same metal ion as defined in [General Formula A-1], G ^D11 and G ^D12 each independently represent a nitrogen atom, a substituted or unsubstituted carbon atom, and J ^D11 , J ^D12 , J ^D13 and J ^D14 represents a group of atoms required to form a 5-membered ring independently of each other, and L ^D11 and L ^D12 represent a linking group.

The exemplary structure of the compound represented by [General Formula E-1] is as follows, but is not limited thereto.

[General Formula F-1]

In the above [General Formula F-1],

M ^E1 represents the same metal ion as defined in [General Formula A-1], and J ^E11 and J ^E12 each independently represent a group of atoms necessary to form a 5-membered ring, G ^E11 , G ^E12 , G ^E13 and G ^E14 each independently represents a nitrogen atom, a substituted or unsubstituted carbon atom, and Y ^E11 , Y ^E12 , Y ^E13 and Y ^E14 each independently represent a nitrogen atom, a substituted or unsubstituted carbon atom.

The exemplary structure of the compound represented by [General Formula F-1] is as follows, but is not limited thereto.

[General formula G-1]

In the above [General Formula G-1],

M ^F1 represents the same metal ion as defined in [General Formula A-1].

L ^F11 , L ^F12 and L ^F13 represent a linking group, R ^F11 , R ^F12 , R ^F13 and R ^F14 represent a substituent, R ^F11 and R ^F12 , R ^F12 And R ^F13 , R ^F13 and R ^F14 may be connected to each other to form a ring, wherein the ring formed by R ^F1 and R ^F12 , R ^F13 and R ^F14 is a 5-membered ring. In addition, Q ^F11 and Q ^F12 represent partial structures containing atoms that bind to M ^F1 .

The exemplary structure of the compound represented by [General Formula G-1] is as follows, but is not limited thereto.

[General Formula H-1] [General Formula H-2] [General Formula H-3]

In the above [General Formula H-1] to [General Formula H-3],

R ¹¹ , R ¹² are alkyl, aryl or heteroaryl substituents; In addition, it is possible to form a fused ring with a substituent adjacent to each other, q11, q12 is an integer of 0 to 4, preferably 0 to 2.

In addition, when q11 and q12 are 2 to 4, a plurality of R11 and R12 may be the same or different, respectively.

L ¹ is a ligand that binds to platinum, and is preferably a ligand capable of forming an ortho metalized platinum complex, a nitrogen-containing heterocyclic ligand, a diketone ligand, or a halogen ligand, and more preferably an ortho metal. It is a ligand forming a platinum complex, a bipyridyl ligand, or a phenanthroline ligand.

n ¹ is an integer from 0 to 3, preferably 0, m ¹ is 1 or 2, and preferably 2.

Moreover, it is preferable that n ¹ and m ¹ are such that the metal complex represented by the general formula H-1 is a neutral complex.

In the above [General Formula H-2],

R ²¹ , R ²² , n ² , m ² , q ²² , L ² are the same as R ¹¹ , R ¹² , n ¹ , m ¹ , q ¹² , L ¹ , respectively, and q ²¹ is an integer from 0 to 2 , 0 is preferred.

In the above [General Formula H-3],

R ³¹ , n ³ , m ³ , L ³ are the same as R ¹¹ , n ¹ , m ¹ , L ¹ , respectively, q ³¹ represents an integer from 0 to 8, 0 to 2 is preferable, and 0 is more desirable.

Examples of specific compounds of [General Formula H-1] to [General Formula H-3] are as follows, but are not limited thereto.

[Formula I-1]

In the above [General Formula I-1],

Ring A, Ring B, Ring C and Ring D represent a nitrogen-containing heterocycle in which any two rings of Rings A to D may have substituents, and the other two rings are aryl or heterocycles in which rings may have substituents It represents and represents an aryl ring, and may form a condensed ring with ring A and ring B, ring A and ring C, and/or ring B and ring D. In X ¹ , X ² , X ³ and X ⁴ , any two of them represent a nitrogen atom that coordinates with a platinum atom, and the other two represent a carbon atom or a nitrogen atom. Q ¹ , Q ² and Q ³ each independently represent a divalent atom (mono) or bond, but Q ¹ , Q ² and Q ³ do not simultaneously represent a bond. Z ¹ , Z ² , Z ³ and Z ⁴ , which 2 represents a coordination bond, and the other 2 represent a covalent bond, an oxygen atom or a sulfur atom.

Examples of the specific compound of [General Formula I-1] are as follows, but are not limited thereto.

[General Formula J-1]

In the above [General Formula J-1],

M represents the same metal ion as defined in [General Formula A-1], Ar1 represents a substituted or unsubstituted ring structure, and two azomethine bonds (-C=N-) that bind to the M In, the nitrogen atom (N) each binds to the M, and as a whole forms a tridentate ligand bonded to the M at three loci.

In addition, in Ar1, C represents a carbon atom constituting the ring structure represented by Ar1. In addition, R1 and R2 may be the same as or different from each other, and each represents a substituted or unsubstituted alkyl group or aryl group, and L represents a monodentate ligand.

In the above [General Formula J-1], it is preferable that M is Pt. Moreover, as said Ar1, it is preferable to select from 5-membered ring, 6-membered ring, and these condensed ring groups.

Examples of the specific compound of [General Formula J-1] are as follows, but are not limited thereto.

In addition, the organic thin film layer may further include various host compounds and various dopant compounds in addition to the organic electroluminescent compound and the dopant compound according to the present invention.

Another aspect of the present invention relates to an organic electroluminescent device comprising a first electrode, a second electrode, and one or more organic thin film layers interposed between the first electrode and the second electrode, wherein the organic thin film layer is represented by [Formula 1] ] To [Formula 2] It includes an organic electroluminescent compound.

In addition, the organic thin film layer containing the organic light-emitting compound of the present invention further includes at least one selected from a functional layer, a light emitting layer, an electron transport layer, and an electron injection layer simultaneously having a hole injection layer, a hole transport layer, a hole injection function and a hole transport function. can do.

At this time, the organic thin film 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, and the organic electroluminescent compound according to the present invention can be used as a host.

Meanwhile, a dopant material may be used in addition to the host in the light emitting layer. When the light emitting layer includes a host and a dopant, the content of the dopant may be generally selected from about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host.

According to an embodiment of the present invention, at least one layer 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 The organic light emitting device according to the present invention may be used in display devices, display devices, and monochrome or white lighting devices.

In the organic electroluminescent device of the present invention, if necessary, additionally known materials for an organic electroluminescent device may be added. For example, a compound that transports holes having a bisarylamino structure or an N-arylcarbazolyl structure or a compound that transports electrons having a benzoimidazolyl structure may be added. Specifically, a material for forming a hole injection and hole transport layer described later or an electron injection material can be used.

In the organic light emitting device of the present invention, at least one organic thin film layer including at least a light emitting layer is sandwiched between a cathode and an anode. And, at least one layer of the organic thin film layer contains the organic electroluminescent compound according to the present invention alone or as a component of a mixture.

The organic electroluminescent compound according to the present invention may be used for a hole injection layer, a hole transport layer, an electron injection layer, and an electron transport layer in addition to the light emitting layer. The organic electroluminescent device according to the present invention is an organic electroluminescent device in which the organic thin film layer is composed of a plurality of layers, specifically (anode/hole injection layer/emission layer/cathode), (anode/light emitting layer/electron injection layer/cathode), (anode) /Hole injection layer/light emitting layer/electron injection layer/cathode), (positive electrode/hole injection layer/hole transport layer/light emitting layer/electron injection layer/cathode) and the like laminated.

In the organic electroluminescent device according to the present invention, the organic thin film layer has a multi-layer structure, so that it is possible to prevent a decrease in luminance or life due to quenching. In addition, a light emitting material, a doping material, a hole injection material, or an electron injection material can be used in combination as necessary. In addition, the luminescence brightness and luminous efficiency may be improved by the doping material. Further, the hole injection layer, the light emitting layer, and the electron injection layer may be formed by two or more layer configurations. In this case, in the case of a hole injection layer, a layer for injecting holes from an electrode is called a hole injection layer, and a layer for receiving holes from the hole injection layer and transporting holes to the light emitting layer is called a hole transport layer. Similarly, in the case of an electron injection layer, a layer that injects electrons from an electrode is called an electron injection layer, and a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer is called an electron transport layer. Each of these layers is selected and used depending on factors such as the energy level of the material, heat resistance, and adhesion to an organic layer or a metal electrode.

As the hole injection material, a compound having the ability to transport holes, a hole injection effect from the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and an excellent thin film forming ability is preferable. Specifically, phthalocyanine derivatives, naphthalocyanine derivatives, porphyrin derivatives, benzidine type triphenylamine, diamine type triphenylamine, hexacyanohexaazatriphenylene, and the like, derivatives thereof, and polyvinylcarbazole, polysilane, conductive polymers, etc. The polymer material may be mentioned, but is not limited to these.

Among the hole injection materials that can be used in the organic electroluminescent device of the present invention, a more effective hole injection material is a phthalocyanine derivative. As phthalocyanine (Pc) derivatives, for example, H2Pc, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl2SiPc, (HO)AlPc, (HO)GaPc, VOPc, TiOPc Phthalocyanine derivatives such as MoOPc and GaPc-O-GaPc and naphthalocyanine derivatives, but are not limited thereto.

In addition, the carrier may be increased or decreased by adding an electron accepting substance such as a TCNQ derivative to the hole injection material. A preferred hole transport material that can be used in the organic EL device of the present invention is an aromatic tertiary amine derivative. Examples of aromatic tertiary amine derivatives include N,N'-diphenyl-N,N'-dinaphthyl-1,1'-biphenyl-4,4'-diamine, N,N,N',N '-Tetrabiphenyl-1,1'-biphenyl-4,4'-diamine, etc., or oligomers or polymers having these aromatic tertiary amine skeletons, but are not limited thereto.

As the electron injecting material, a compound having the ability to transport electrons, an electron injecting effect from the cathode, an excellent electron injecting effect to the light emitting layer or the light emitting material, and excellent in the ability to form a thin film is preferable. In the organic EL device of the present invention, more effective electron injection materials are metal complex compounds and nitrogen-containing heterocyclic derivatives.

Examples of the metal complex compound include 8-hydroxyquinolinate lithium, bis(8-hydroxyquinolinate) zinc, tris(8-hydroxyquinolinate)aluminum, and tris(8-hydroxyquinoline) Nate) gallium, bis(10-hydroxybenzo[h]quinolinate) beryllium, bis(10-hydroxybenzo[h]quinolinate) zinc, etc. are mentioned, but it is not limited to this.

As the nitrogen-containing heterocyclic derivative, for example, oxazole, thiazole, oxadiazole, thiadiazole, triazole, pyridine, pyrimidine, triazine, phenanthroline, benzimidazole, imidazopyridine and the like are preferable. And, among them, benzimidazole derivatives, phenanthroline derivatives, and imidazopyridine derivatives are preferable.

In a preferred embodiment, these electron injecting materials further contain dopants, and more preferably dopants represented by alkali metals in the vicinity of the cathode interface of the second organic layer in order to facilitate receiving electrons from the cathode. Examples of the dopant include an electron donating metal, an electron donating metal compound, and an electron donating metal complex, and these reducing dopants may be used alone or in combination of two or more.

In the organic electroluminescent device of the present invention, in addition to at least one selected from organic electroluminescent compounds in the light emitting layer, at least one of a light emitting material, a doping material, a hole injection material, a hole transport material and an electron injection material will be contained in the same layer. It might be. In addition, it is possible to provide a protective layer on the surface of the element to improve the stability of the organic light emitting element obtained by the present invention against temperature, humidity, atmosphere, etc., or to protect the entire element with silicone oil, resin, or the like.

As the conductive material used for the anode of the organic electroluminescent device of the present invention, it is suitable to have a work function greater than 4 eV, carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum, palladium, etc. And their alloys, metal oxides such as tin oxide and indium oxide used in ITO substrates and NESA substrates, and organic conductive resins such as polythiophene and polypyrrole. As the conductive material used for the negative electrode, it is suitable to have a work function smaller than 4 eV, and magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum, lithium fluoride and the like and alloys thereof are used. , It is not limited to this. As an alloy, magnesium/silver, magnesium/indium, lithium/aluminum, etc. are mentioned as a representative example, but it is not limited to these. The ratio of the alloy is controlled according to the temperature, atmosphere, vacuum degree, etc. of the evaporation source, and is selected in an appropriate ratio. The positive electrode and the negative electrode may be formed by a layer structure of two or more layers, if necessary.

In the organic light emitting device of the present invention, in order to emit light efficiently, it is preferable that at least one side is sufficiently transparent in the light emission wavelength range of the device. Moreover, it is preferable that the substrate is also transparent. The transparent electrode is set to ensure a predetermined light transmittance by a method such as vapor deposition or sputtering, by using the above-described conductive material. It is preferable that the light-transmitting electrode has a light transmittance of 10% or more. The substrate is not limited as long as it has mechanical and thermal strength and transparency, and there are glass substrates and transparent resin films.

For the formation of each layer of the organic electroluminescent device of the present invention, any of a dry deposition method such as vacuum deposition, sputtering, plasma, and ion plating, or a wet deposition method such as spin coating, dipping, flow coating may be applied. . The film thickness is not particularly limited, but it is necessary to set it to an appropriate film thickness. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. If the film thickness is too thin, pinholes or the like are generated, and sufficient luminescence brightness is not obtained even when an electric field is applied. The typical film thickness is preferably in the range of 5 nm to 10 μm, more preferably in the range of 10 nm to 0.2 μm.

In the case of a wet film-forming method, the material forming each layer is dissolved or dispersed in a suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane to form a thin film, and any of the solvents may be used. As a solution suitable for such a wet film forming method, a solution containing an organic electroluminescent material containing the aromatic amine derivative of the present invention and a solvent can be used as the organic electroluminescent material.

The organic light emitting device of the present invention can be used for flat light emitters such as flat panel displays of wall-mounted televisions, copiers, printers, light sources such as backlights or instruments for liquid crystal displays, display panels, signs, and the like. In addition, the compounds of the present invention can be used not only in organic electroluminescent devices, but also in fields such as electrophotographic photoreceptors, photoelectric conversion devices, solar cells, and image sensors.

In addition, if a person with ordinary knowledge in the technical field to which the present invention pertains is based on common sense upon application and the disclosure of the present invention, the compound described in the claims of the present invention can be easily prepared without excessive trial and error or high-level experiment. It is obvious that it can be utilized.

That is, although not all described in the following examples, according to the experiment results of the present inventors, the size, orientation, possibility of steric hindrance, polarity difference, etc., of the substituents between the compounds described in the examples below and the compounds not described in the examples are at a glance Even if it seems possible, the specific manufacturing process described in the following examples is not very complicated and does not involve complicated side reactions, and those skilled in the art of the present invention can use the following technical knowledge at the time of filing. It is apparent that the compounds described in the claims of the present invention can be produced without adding special knowledge only by describing the specific manufacturing method of the examples.

Hereinafter, the present invention will be described in more detail by examples. However, the following examples are presented as examples only, and the present invention is not limited by them.

Synthetic example 1. Synthesis of Formula 3

Synthetic example 1-1. Synthesis of <1-a>

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

[Scheme 1]

<1-a>

In a 2000 mL round-bottom flask, 250 g of N,N-diethylformamide was added with 100 g of carbazole (0.598 mol) under nitrogen, stirred, and the temperature of the reactant was cooled to 0°C. 106-44 g (0.598 mol) of N-bromosuccinimide was dissolved in 530 mL of N,N-dimethylamide and added dropwise. After dropping, the mixture was stirred at room temperature. When the reaction was completed, the resultant product was poured into water, stirred, filtered and washed with water and methanol to obtain 76.4 g (51.9%) of <1-a>.

Synthetic example 1-2. Synthesis of <1-b>

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

[Scheme 2]

<1-b>

In a 2 L round bottom flask, 39.5 g (1.7 mol) of magnesium, 10 g of iodine and 100 mL of tetrahydrofuran were added and refluxed for 2 hours under nitrogen. After cooling to room temperature, 212.8 g (1.4 mol) of bromobenzene was dissolved in 200 mL of tetrahydrofuran and slowly added dropwise. After dropwise addition, the mixture was refluxed for 2 hours and cooled to room temperature. In another 2 L round bottom flask, 100 g (0.54 mol) of cyanuric chloride was dissolved in 200 mL of tetrahydrofuran, and the reaction solution was cooled to 0°C. The previous reaction solution was slowly added dropwise while maintaining the temperature at 0°C. After completion of the reaction, the reaction was terminated with 4 M hydrochloric acid aqueous solution, extracted, and then the organic layer was concentrated under reduced pressure, recrystallized with hexane, and dried to obtain 100 g (68.9%) of the compound represented by Chemical Formula 1-b.

Synthetic example 1-3. Synthesis of <1-c>

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

[Scheme 3]

<1-c>

In a 500 mL round-bottom flask, add sodium hydride (60% mineral oil) (NaH), 0.94 g (0.024 mol), and 100.0 mL of N,N-dimethylformamide in a nitrogen atmosphere, and cool the reaction solution to 0°C. The solution obtained by dissolving 10 g (0.019 mol) of the compound represented by 1-a synthesized in Reaction Scheme 3 at 0° C. in 100 mL of N,N-dimethylformamide is slowly added dropwise, followed by dropwise addition, maintaining at 0° C. and stirring for 1 hour. . After 1 hour, a solution in which 6.5 g (0.024 mol) of the compound represented by 1-b synthesized in Scheme 2 was dissolved in 100 mL of N,N-dimethylformamide was slowly added dropwise. When the dropwise addition is completed, the reaction solution is raised to room temperature and stirred. When the reaction is completed, the reaction solution is poured into 1 L of water to precipitate a solid, and then filtered. The solid was recrystallized using toluene to obtain 5.9 g (41.1%) of the compound represented by Formula 2.

Synthetic example 1-4. Synthesis of <1-d>

<1-d> was synthesized by the following scheme 4.

[Reaction Scheme 4]

<1-d>

In a 500 mL round-bottom flask, 40 g (0.3699 mol) of phenylhydrazine, 41.5 g (0.3699 mol) of 2-methyl cyclohexanone, and 240 mL of acetic acid were added and refluxed for 6 hours. After the reaction is completed, the reaction solution is basified with sodium hydroxide. After neutralizing by extracting with water and ethylene acetate, the organic layer was anhydrously treated with magnesium sulfate, concentrated under reduced pressure, and <7.5> (84%) obtained by separating by column chromatography using hexane and methylene chloride as a developing solvent. ) Was prepared.

Synthetic example 1-5. Synthesis of <1-e>

<1-e> was synthesized by the following Reaction Scheme 5.

[Scheme 5]

<1-e>

50 g (0.2699 mol) of <1-d> obtained from Formula 1 was dissolved in 150 mL of toluene in a 500 mL round-bottom flask in a nitrogen atmosphere, and the furnace was lowered to minus 20 degrees Celsius. 260 mL (0.1753 mol) of 1.6 M methyllithium was slowly added dropwise to the above solution and reacted for 3 hours at minus 20 degrees. After the reaction is completed, 200 mL of a 1:1 solution of toluene and water is slowly poured into the reaction solution. After layer separation, the organic layer was anhydrous treated with magnesium sulfate, concentrated under reduced pressure, and 47.3 g (87%) of <1-e> obtained by separating by column chromatography using hexane and methylene chloride as a developing solvent was prepared.

Synthetic example 1-6. Synthesis of <1-f>

<1-f> was synthesized by the following Reaction Scheme 6.

[Scheme 6]

<1-f>

<1-b> 40.0 g (0.199 mol), bromobenzene 37.44 g (0.238 mol), Pd ₂ (dba) ₃ 3.6 g (0.004 mol) in 1 L round-bottom flask, 38.19 g (0.397) mol), BINAP 2.47g (0.004 mol) is added and dissolved in toluene. Reflux for 8 hours. Check whether the reaction is complete by TLC. After the reaction is completed, the organic layer is concentrated after filtration. Separation by column chromatography (developing solvent MC:Hex=1:3). <1-f> 40.4g (73.3%) was prepared.

Synthetic example 1-7. Synthesis of <1-g>

<1-g> was synthesized by the following scheme 7.

[Scheme 7]

<1-g>

40.0 g (0.144 mol) of <1-f> in a 1 L reaction vessel was dissolved in 400 mL of chloroform, and the temperature of the reactor was lowered to 0 degrees. After diluting 23.0 g of bromine (0.144 mol) in 120 mL of chloroform, it was slowly added dropwise to the reaction vessel. After the dropwise addition, the temperature was slowly raised to room temperature and stirred for 8 hours. Check whether the reaction is complete by TLC. When the reaction is over, add 100 mL of water and remove bromine with sodium thiosulfate. Extract with chloroform and water. The organic layer is concentrated and recrystallized from ethanol. Repeat recrystallization with methylene chloride and ethanol to increase purity. <1-g> was prepared 37.1 g (72.2%).

Synthetic example 1-8. Synthesis of <1-h>

<1-h> was synthesized by the following Reaction Scheme 8.

[Scheme 8]

<1-h>

<1-g> 35.0g (0.098mol), bis(pinacolato)diboron 37.4g (0.147mol), PdCl2(dppf) 1.6g (0.002mol), potassium acetate 28.90g (0.295mol) in 1L round bottom flask ) Is added, and 525 mL of toluene is added and refluxed at 110 degrees for 12 hours. When the reaction is complete, filter under reduced pressure in a hot state. After drying the solution, 27.7 g (69.9%) of <1-h> was prepared using methylene chloride and normal hexane as column solvents using column chromatography.

Synthetic example 1-9. < Compound 3 > Synthesis of

<Compound 3> was synthesized by the following Reaction Scheme 9.

[Scheme 9]

<Compound 3>

In a 250 mL round-bottom flask, <1-c> 20.0 g (0.071 mol), <1-h> 21.2 g (0.086 mol), tetrakistriphenylphosphine palladium (0) 1.7 g (0.001 mol), potassium carbonate 19.7 g (0.143 mol) was added, 100 mL of 1,4-dioxane, 100 mL of toluene, and 40 mL of water were added, followed by stirring at 80°C for 6 hours. Upon completion of the reaction, the organic layer was extracted and dried, and 18.4 g (63.9%) of <Compound 3> was prepared by column chromatography.

MS [M] ⁺ 673

Synthetic example 2. Synthesis of Formula 17

Synthetic example 2-1. Synthesis of <2-a>

<2-a> was synthesized by the following scheme 10.

[Scheme 10]

<2-a>

<2-a> was synthesized by the same method except that 2-bromonaphthalene was used instead of bromobenzene used in Scheme 6.

Synthetic example 2-2. Synthesis of <2-b>

<2-b> was synthesized by the following Reaction Scheme 11.

[Scheme 11]

<2-b>

<2-b> was synthesized by the same method, except that <2-a> was used instead of <1-e> used in Scheme 7.

Synthetic example 2-3. Synthesis of <2-c>

<2-c> was synthesized by the following Reaction Scheme 12.

[Scheme 12]

<2-c>

<2-c> was synthesized by the same method, except that <2-b> was used instead of <1-g> used in Scheme 8.

Synthetic example 2-4. Synthesis of <2-d>

<2-d> was synthesized by the following scheme 13.

[Scheme 13]

<2-d>

<2-d> was synthesized in the same manner, except that 3-bromocarbazole instead of <1-c> used in Scheme 9 and <2-c> instead of <1-h> were used.

Synthetic example 2-5. Synthesis of <2-e>

<2-e> was synthesized by the following scheme 14.

[Scheme 14]

<2-e>

Chlorodiphenyltriazine 20.0g (74.7mmol), 4-bromophenylboronic acid 18.0g (89.7mmol), tetrakis(triphenylphosphine)palladium 1.7g (1.5mmol), potassium carbonate 20.7g (149.4mmol) ), 1,4-dioxane 100 mL, toluene 100 mL, distilled water into 50 mL and stirred at 100 ℃ for 12 hours.

When the reaction is complete, extraction is performed using ethyl acetate and distilled water. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and recrystallized with methylene chloride and acetone to obtain 23.2 g (80%) of the compound represented by 2-e.

Synthetic example 2-6. Synthesis of <Compound 17>

<Compound 17> was synthesized by the following Reaction Scheme 15.

[Scheme 15]

<Compound 17>

<Compound 17> was synthesized by the same method except that <2-e> instead of bromobenzene used in Scheme 6 and <2-d> instead of <1-b> were used.

MS [M] ⁺ 800

Synthetic example 3. Synthesis of Formula 33

Synthetic example 3-1. Synthesis of <3-a>

<3-a> was synthesized by the following Reaction Scheme 16.

[Scheme 16]

<3-a>

In a 2000 mL round bottom flask, 100.0 g (0.318 mol) of tribromobenzene, 89.1 g (0.731 mol) of phenylboronic acid, 18.4 g (0.016 mol) of tetrakistriphenylphosphine palladium (0), 219.5 g of potassium carbonate (1.588 mol) was added, 500 mL of 1,4-dioxane, 500 mL of toluene, and 2000 mL of water were added, followed by stirring at 80°C for 6 hours. Upon completion of the reaction, extraction was performed to dry the organic layer, and 54.3 g (42.9%) of <3-a> was prepared by column chromatography.

Synthetic example 3-2. Synthesis of <3-b>

<3-b> was synthesized by the following scheme 17.

[Scheme 17]

<3-b>

<3-b> was synthesized by the same method, except that <3-a> was used instead of bromobenzene used in Scheme 6.

Synthetic example 3-3. Synthesis of <3-c>

<3-c> was synthesized by the following scheme 18.

[Reaction Scheme 18]

<3-c>

<3-c> was synthesized in the same manner, except that <3-b> was used instead of <1-f> used in Scheme 7.

Synthetic example 3-4. Synthesis of <3-d>

<3-d> was synthesized by the following Reaction Scheme 19.

[Scheme 19]

<3-d>

<3-d> was synthesized by the same method, except that <3-c> was used instead of <1-g> used in Scheme 8.

Synthetic example 3-5. Synthesis of <3-e>

<3-e> was synthesized by the following scheme 20.

[Scheme 20]

<3-e>

<3-e> was synthesized in the same manner, except that 3-bromocarbazole instead of <1-c> used in Scheme 9 and <3-d> instead of <1-g> were used.

Synthetic example 3-6. Synthesis of <3-f>

<3-f> was synthesized by the following Reaction Scheme 21.

[Scheme 21]

<3-f>

<3-f> was synthesized by the same method except that 3-bromophenylboronic acid was used instead of 4-bromophenylboronic acid used in Scheme 14.

Synthetic example 3-7. Synthesis of <Compound 33>

<Compound 33> was synthesized by the following Reaction Scheme 22.

[Scheme 22]

<Compound 33>

<Compound 33> was synthesized by the same method except that <3-f> instead of bromobenzene used in Scheme 6 and <3-e> instead of <1-b> were used.

MS [M] ⁺ 902

Synthetic example 4. Synthesis of Formula 86

Synthetic example 4-1. Synthesis of <4-a>

<4-a> was synthesized by the following scheme 23.

[Scheme 23]

<4-a>

In a 1000 mL round-bottom flask, 25 g (0.128 mol) of 4-bromoindole and 500 mL of acetic acid were added under nitrogen and stirred, and the reaction temperature was cooled to 0 degrees. 24.5 g (0.390 mol) of sodium cyanoborohydride was slowly added. After putting it, it was stirred at room temperature. After the reaction was completed, the resultant product was poured into water, stirred, basified with sodium hydroxide, extracted, and then the organic layer was concentrated under reduced pressure and purified by column chromatography with hexane to obtain 17.2 g (51.9%) of formula <4-a>. .

Synthetic example 4-2. Synthesis of <4-b>

<4-b> was synthesized by Reaction Scheme 24 below.

[Scheme 24]

<4-b>

<4-b> was synthesized in the same manner, except that <4-a> instead of <1-b> used in Scheme 6 and 1-iodonaphthalene instead of bromobenzene were used.

Synthetic example 4-3. Synthesis of <4-c>

<4-c> was synthesized by the following Reaction Scheme 25.

[Reaction Scheme 25]

<4-c>

<4-c> was synthesized by the same method, except that <4-b> was used instead of <1-g> used in Scheme 8.

Synthetic example 4-4. Synthesis of <Compound 86>

<Compound 86> was synthesized by the following reaction formula 26.

[Scheme 26]

<Compound 86>

<Compound 86> was prepared by synthesizing in the same manner, except that <4-c> was used instead of <1-h> used in Scheme 9.

MS [M] ⁺ 641

Synthetic example 5. Synthesis of Formula 107

Synthetic example 5-1. Synthesis of <5-a>

<5-a> was synthesized by the following Reaction Scheme 27.

[Scheme 27]

<5-a>

<5-a> was synthesized by the same method except that 1,2,3,4-tetrahydroquinoline was used instead of <1-f> used in Scheme 7.

Synthetic example 5-2. Synthesis of <5-b>

<5-b> was synthesized by the following scheme 28.

[Scheme 28]

<5-b>

<5-b> was synthesized in the same manner, except that <5-a> instead of <1-b> used in Scheme 6 and iodobenzene instead of bromobenzene were used.

Synthetic example 5-3. Synthesis of <5-c>

<5-c> was synthesized by the following scheme 29.

[Scheme 29]

<5-c>

<5-c> was synthesized by the same method, except that <5-b> was used instead of <1-g> used in Scheme 9.

Synthetic example 5-4. Synthesis of <5-d>

<5-d> was synthesized by the following scheme 30.

[Scheme 30]

<5-d>

<5-d> was synthesized by the same method except that 3-bromocarbazole instead of <1-c> used in Scheme 9 and <5-c> instead of <1-h> were used.

Synthetic example 5-5. Synthesis of <Compound 107>

<Compound 107> was synthesized by the following Reaction Scheme 31.

[Scheme 31]

<Compound 107>

<Compound 107> was prepared in the same manner as in <6e> instead of <2-e> and <1-b> instead of bromobenzene used in Scheme 6.

MS [M] ⁺ 681

Synthetic example 6. Synthesis of Formula 115

Synthetic example 6-1. Synthesis of <6-a>

<6-a> was synthesized by the following scheme 32.

[Scheme 32]

<6-a>

<5-a> was prepared in the same manner as in <6-b> used in Scheme 6, except that dihydrobenzozine and bromobenzene instead of iodobenzene were used.

Synthetic example 6-2. Synthesis of <6-b>

<6-b> was synthesized by the following Reaction Scheme 33.

[Reaction Scheme 33]

<6-b>

<6-b> was synthesized by the same method, except that <6-a> was used instead of <1-g> used in Scheme 7.

Synthetic example 6-3. Synthesis of <6-c>

<6-c> was synthesized by the following scheme 34.

[Scheme 34]

<6-c>

<6-c> was synthesized by the same method, except that <6-b> was used instead of <1-g> used in Scheme 8.

Synthetic example 6-4. Synthesis of <Compound 115>

<Compound 115> was synthesized by the following reaction formula 35.

[Scheme 35]

<Compound 115>

<Compound 115> was prepared by synthesizing in the same manner, except that <6-c> was used instead of <1-h> used in Scheme 9.

MS [M] ⁺ 607

Synthetic example 7. Synthesis of Formula 146

Synthetic example 7-1. Synthesis of <7-a>

<7-a> was synthesized by the following scheme 36.

[Scheme 36]

<7-a>

In a 5 L round-bottom flask, 4-bromo-iodinebenzene 200 g (0.707 mol), 1-naphthylboronic acid 121.6 g (0.707 mol), Pd(PPh ₃ ) ₄ 16.4 g (0.014 mol), potassium carbonate 195.4 g (1.414 mol) was added, and 1000 mL of tetrahydrofuran, 1000 mL of toluene, and 400 mL of water were added and refluxed for 12 hours. TLC confirms the completion of the reaction. When the reaction is completed, the organic layer is dried by extraction. It was prepared by column chromatography <7-a> 120.1g (60.0%).

Synthetic example 7-2. Synthesis of <7-b>

<7-b> was synthesized by the following scheme 37.

[Scheme 37]

<7-b>

<7-b> was synthesized in the same manner, except that 3-bromocarbazole instead of <1-e> used in Scheme 6 and <7-a> instead of bromobenzene were used.

Synthetic example 7-3. Synthesis of <7-c>

<7-c> was synthesized by the following scheme 38.

[Scheme 38]

<7-c>

<7-c> was synthesized by the same method, except that <7-b> was used instead of <1-g> used in Scheme 8.

Synthetic example 7-4. Synthesis of <7-d>

<7-d> was synthesized by the following reaction formula 39.

[Scheme 39]

<7-d>

<7-d> was synthesized by the same method except that <1-e> instead of <1-c> and <7-c> instead of <1-h> used in Scheme 9.

Synthetic example 7-5. Synthesis of <Compound 146>

<Compound 146> was synthesized by the following scheme 40.

[Reaction Scheme 40]

<Compound 146>

<Compound 146> was synthesized in the same manner as in <6-d> instead of <3-f> and <1-b> instead of bromobenzene used in Scheme 6.

MS [M] ⁺ 876

Synthetic example 8. Synthesis of Formula 196

Synthetic example 8-1. Synthesis of <8-a>

<8-a> was synthesized by the following scheme 41.

[Scheme 41]

<8-a>

<8-a> was prepared by synthesizing in the same manner, except that D5-bromobenzene was used instead of bromobenzene used in Scheme 6.

Synthetic example 8-2. Synthesis of <8-b>

<8-b> was synthesized by the following scheme 42.

[Reaction Scheme 42]

<8-b>

<8-b> was synthesized by the same method, except that <8-a> was used instead of <1-f> used in Scheme 7.

Synthetic example 8-3. Synthesis of <8-c>

<8-c> was synthesized by the following scheme 43.

[Scheme 43]

<8-c>

<8-c> was prepared by synthesizing in the same manner, except that iodobenzene was used instead of bromobenzene used in Scheme 6.

Synthetic example 8-4. Synthesis of <8-d>

<8-d> was synthesized by the following scheme 44.

[Scheme 44]

<8-d>

<8-d> was synthesized by the same method, except that <8-c> was used instead of <1-g> used in Scheme 8.

Synthetic example 8-5. <Compound 196> Synthesis of

<Compound 196> was synthesized by the following reaction formula 45.

[Scheme 45]

<Compound 196>

<Compound 196> was synthesized by the same method as <8-b> instead of <1-c> and <8-d> instead of <1-h> used in Scheme 9.

MS [M] ⁺ 523

Synthetic example 9. Synthesis of Formula 235

Synthetic example 9-1. Synthesis of <9-a>

<9-a> was synthesized by the following Reaction Scheme 46.

[Scheme 46]

<9-a>

<9-a> was prepared by synthesizing in the same manner, except that bromobinaphthyl was used instead of bromobenzene used in Scheme 6.

Synthetic example 9-2. Synthesis of <9-b>

<9-b> was synthesized by the following Reaction Scheme 47.

[Scheme 47]

<9-b>

<2-b> was synthesized in the same manner, except that <2-a> was used instead of <1-f> used in Scheme 7.

Synthetic example 9-3. Synthesis of <9-c>

<9-c> was synthesized by the following reaction formula 48.

[Scheme 48]

<9-c>

<9-c> was synthesized by the same method except that 2-bromocarbazole was used instead of <1-g> used in Scheme 8.

Synthetic example 9-4. Synthesis of <9-d>

<9-d> was synthesized by the following Reaction Scheme 49.

[Reaction Scheme 49]

<9-d>

<9-d> was synthesized by the same method, except that <9-b> instead of <1-c> used in Scheme 9 and <9-c> instead of <1-h> were used.

Synthetic example 9-5. Synthesis of <Compound 235>

<Compound 235> was synthesized by the following reaction formula 50.

[Reaction Scheme 50]

<Compound 235>

<Compound 235> was synthesized in the same manner as in <6-d> instead of <2-e> and <1-b> instead of bromobenzene used in Scheme 6.

MS [M] ⁺ 826

Example : Preparation of organic light emitting diodes

The ITO glass was patterned to have a light emitting area of 2 mm×2 mm, and then washed. After mounting the substrate in the vacuum chamber, the base pressure was 1 × 10 ^-6 torr, and then the organic material was placed on the ITO DNTPD (700 700), NPD (300 Å), the compound prepared by the present invention + (piq)2Ir (acac) (10%) (300 Å), Alq ₃ (350 Å), LiF (5 Å), Al (1,000 Å) It was deposited in the order of, was measured at 0.4 mA.

Comparative example

The organic light emitting diode device for the comparative example was manufactured in the same manner except that CBP, which is generally used as a phosphorescent host material, was used instead of the compound prepared by the invention in the device structure of the above embodiment, and the structure of the CBP is as follows.

<CBP>

division Host Dopant Doping concentration% V Cd/㎡ CIEx CIEy Comparative Example 1 CBP (piq)2Ir(acac) 10 7.50 1000 0.671 0.329 Example 1 3 (piq)2Ir(acac) 10 4.00 1611 0.673 0.327 Example 2 15 (piq)2Ir(acac) 10 3.06 1562 0.671 0.328 Example 3 17 (piq)2Ir(acac) 10 3.57 1594 0.672 0.327 Example 4 27 (piq)2Ir(acac) 10 3.24 1579 0.670 0.329 Example 5 33 (piq)2Ir(acac) 10 3.37 1678 0.672 0.326 Example 6 54 (piq)2Ir(acac) 10 4.02 1478 0.671 0.327 Example 7 68 (piq)2Ir(acac) 10 3.84 1542 0.673 0.327 Example 8 83 (piq)2Ir(acac) 10 3.98 1524 0.671 0.326 Example 9 86 (piq)2Ir(acac) 10 3.47 1631 0.671 0.326 Example 10 99 (piq)2Ir(acac) 10 4.13 1597 0.672 0.325 Example 11 106 (piq)2Ir(acac) 10 3.71 1538 0.673 0.326 Example 12 107 (piq)2Ir(acac) 10 3.86 1473 0.672 0.326 Example 13 115 (piq)2Ir(acac) 10 3.46 1582 0.672 0.325 Example 14 122 (piq)2Ir(acac) 10 3.99 1486 0.673 0.325 Example 15 127 (piq)2Ir(acac) 10 3.06 1543 0.672 0.326 Example 16 141 (piq)2Ir(acac) 10 3.91 1527 0.673 0.326 Example 17 146 (piq)2Ir(acac) 10 4.03 1671 0.671 0.327 Example 18 176 (piq)2Ir(acac) 10 3.87 1472 0.672 0.326 Example 19 190 (piq)2Ir(acac) 10 4.16 1549 0.672 0.327 Example 20 196 (piq)2Ir(acac) 10 3.94 1574 0.673 0.327 Example 21 228 (piq)2Ir(acac) 10 3.74 1592 0.673 0.326 Example 22 231 (piq)2Ir(acac) 10 3.54 1608 0.673 0.326

In addition, even if the compounds included in the scope of the present invention or a combination thereof, some compounds may cause problems in which emission uniformity at high temperatures may not be secured, the compounds of Formulas 3 to 245 above are very Not only can excellent luminous uniformity be secured, but also the luminous uniformity on the basis of area and time does not deteriorate even after an electric field is applied for a long time (for example, over 100 hours). And it was confirmed that it shows a specific effect that the uniformity of light emission based on the area and time is secured even after a long operation of 100 hours or more.

In addition, even if the combination of the compounds included in the scope of the present invention (for example, formula VW), it was impossible to express a viscosity of 7 cP or higher without using a separate thickener, and thus film formation by the solution coating method was mostly impossible. Formula 1, 15, 17, 27, 33, 54, 68, 83, 86, 99, 106, 107, 115, 122, 127, 141, 146, 176, 190, 196, 228 selected from the above, or When using these mixtures, it was confirmed that an effect of forming a film by a solution coating method was possible because a viscosity of 7 cP or more could be expressed without using a separate thickener.

Claims (11)

An organic electroluminescent compound represented by the following [Formula 1] or [Formula 2]:
[Formula 1] [Formula 2]

[Structural Formula 1]

In the above [Formula 1] to [Formula 2],
X ₁ and X ₂ are each CRR, X ₃ and X ₄ are each CR,
Y is a single bond, or selected from CRR, O and S (wherein R is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms),
L ₁ and L ₂ are each independently a single bond or a divalent linking group selected from substituted or unsubstituted arylene having 6 to 50 carbon atoms and substituted or unsubstituted heteroarylene having 3 to 50 carbon atoms, m and n. Is an integer of 0 to 4, and when m or n is 2 or more, a plurality of L ₁ and L ₂ may be the same or different, respectively,
R ₁ to R ₂ are the same or different from each other, and each is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, substituted or unsubstituted aryl group having 6 to 60 carbon atoms and substituted or unsubstituted It is selected from the group consisting of a heteroaryl group having 3 to 60 carbon atoms, R ₃ to R ₆ are each hydrogen,
Any one of R ₁ and R ₃ to R ₆ is connected to [Structural Formula 1] (connected in'*' of Structural Formula 1). According to claim 1,
R ₁ to R ₂ , L ₁ and L ₂ are each independently hydrogen, deuterium, halogen group, cyano group, alkyl group having 1 to 60 carbon atoms, aryl group having 6 to 60 carbon atoms, heteroaryl group having 2 to 60 carbon atoms, and An organic electroluminescent compound, characterized in that it is further substituted with one or more substituents selected from alkylsilyl groups having 1 to 10 carbon atoms. delete delete delete According to claim 1,
The organic electroluminescent compound represented by [Chemical Formula 1] or [Chemical Formula 2] is any one selected from the following [Chemical Formula 3] to [Chemical Formula 245]:

[Formula 3] [Formula 4] [Formula 5] [Formula 6]

[Formula 7] [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] [Formula 117] [Formula 118]

[Formula 119] [Formula 120] [Formula 121] [Formula 122]

[Formula 123] [Formula 124] [Formula 125] [Formula 126]

[Chemical Formula 127] [Chemical Formula 128] [Chemical Formula 129] [Chemical Formula 130]

[Chemical Formula 131] [Chemical Formula 132] [Chemical Formula 133] [Chemical Formula 134]

[Formula 135] [Formula 136] [Formula 137] [Formula 138]

[Formula 139] [Formula 140] [Formula 141] [Formula 142]

[Formula 143] [Formula 144] [Formula 145] [Formula 146]

[Formula 147] [Formula 148] [Formula 149] [Formula 150]

[Chemical Formula 151] [Chemical Formula 152] [Chemical Formula 153] [Chemical Formula 154]

[Formula 155] [Formula 156] [Formula 157] [Formula 158]

[Formula 159] [Formula 160] [Formula 161] [Formula 162]

[Formula 163] [Formula 164] [Formula 165] [Formula 166]

[Chemical Formula 167] [Chemical Formula 168] [Chemical Formula 169] [Chemical Formula 170]

[Formula 171] [Formula 172] [Formula 173] [Formula 174]

[Formula 175] [Formula 176] [Formula 177] [Formula 178]

[Formula 179] [Formula 180] [Formula 181] [Formula 182]

[Formula 183] [Formula 184] [Formula 185] [Formula 186]

[Formula 187] [Formula 188] [Formula 189] [Formula 190]

[Formula 191] [Formula 192] [Formula 193] [Formula 194]

[Formula 195] [Formula 196] [Formula 197] [Formula 198]

[Formula 199] [Formula 200] [Formula 201] [Formula 202]

[Formula 203] [Formula 204] [Formula 205] [Formula 206]

[Formula 207] [Formula 208] [Formula 209] [Formula 210]

[Formula 211] [Formula 212] [Formula 213] [Formula 214]

[Formula 215] [Formula 216] [Formula 217] [Formula 218]

[Formula 219] [Formula 220] [Formula 221] [Formula 222]

[Formula 223] [Formula 224] [Formula 225] [Formula 226]

[Formula 227] [Formula 228] [Formula 229] [Formula 230]

[Formula 231] [Formula 232] [Formula 233] [Formula 234]

[Formula 235] [Formula 236] [Formula 237] [Formula 238]

[Formula 239] [Formula 240] [Formula 240] [Formula 241]

[Formula 243] [Formula 244] [Formula 245] An organic thin film layer for an organic light emitting device, comprising at least one compound according to claim 1. The method of claim 7,
The organic thin film layer is an organic thin film layer, characterized in that the organic light emitting compound represented by the [formula 1] or [formula 2] as a host, and further comprises at least one dopant compound. A first electrode; A second electrode; And an organic thin film layer according to claim 7 interposed between the first electrode and the second electrode. The method of claim 9,
The organic light emitting device further includes at least one layer selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron blocking layer between the first electrode and the second electrode. ,
An organic electroluminescent device characterized in that one of the light emitting layer, hole injection layer, hole transport layer, hole blocking layer, electron transport layer, electron injection layer and electron blocking layer is the organic thin film layer according to claim 7. The method of claim 9,
The organic electroluminescent device comprises at least one organic light emitting layer that emits blue, red or green light, and emits white light.