Organic light-emitting devices

Abstract

The present specification provides an organic light-emitting device including an organic material layer.

Description

Technical Field

[0001] This specification relates to organic light emitting devices.

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2019-0057177 filed in the Korean Intellectual Property Office on May 15, 2019, the entire contents of which are incorporated herein by reference. Background Art

[0003] Generally, the organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy by using organic materials. An organic light emitting device utilizing the organic light emitting phenomenon generally has a structure including a positive electrode, a negative electrode, and an organic material layer disposed therebetween. Here, in many cases, in order to improve the efficiency and stability of the organic light emitting device, the organic material layer may have a multilayer structure composed of different materials, and may be composed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.

[0004] In order to improve the performance of organic light emitting devices, research on using appropriate materials in appropriate organic material layers in the structure of the organic light emitting devices has been continuously conducted.

[0005] [Prior art document] (Patent document 1) Korean Patent No. 10-1347240 Summary of the invention

[0006] Technical issues

[0007] The present specification is devoted to providing an organic light-emitting material having good performance and an organic light-emitting device including the same by evaluating the reversibility of materials for organic light-emitting devices, namely, electrical stability in (+) radical and (-) radical states, using cyclic voltammetry (CV).

[0008] Technical Solution

[0009] An exemplary embodiment of the present specification provides an organic light emitting device including: a positive electrode; a negative electrode; and an organic material layer disposed between the positive electrode and the negative electrode.

[0010] In an exemplary embodiment, the organic material layer includes a hole transport material (HT), and the HOMO absolute value of the hole transport material (HT) is 4.30 eV to 4.60 eV, and the reversibility value (I ) in the oxidation range at a scan rate of 100 mV / sec when measuring the cyclic voltage current is 0.18 V to 0.22 V. r / I f ) is 0.83 or higher.

[0011] In another exemplary embodiment, the organic material layer includes an electron blocking material (EB), and when the cyclic voltage current is measured, the reversibility value (I ) of the electron blocking material (EB) in the oxidation range at a scan rate of 100 mV / sec is r / I f ) is greater than 0.5.

[0012] In yet another exemplary embodiment, the organic material layer includes a blue light emitting dopant material (BD), and the LUMO absolute value of the blue light emitting dopant material (BD) is 2.40 eV to 2.74 eV, and the reversibility value (I ) in the reduction range at a scan rate of 100 mV / sec when measuring the cyclic voltage current is 2.40 eV to 2.74 eV. r / I f ) is greater than [-23.14+8.458×(LUMO absolute value)].

[0013] In yet another exemplary embodiment, the organic material layer includes an electron transport material (ET), and the LUMO absolute value of the electron transport material (ET) is 2.60 eV to 2.90 eV, and the reversibility value (I ) in the reduction range at a scan rate of 100 mV / sec when measuring the cyclic voltage current is less than 2.60 eV to 2.90 eV. r / I f ) is greater than [4.96-1.535×(LUMO absolute value)].

[0014] In another exemplary embodiment, the organic material layer includes a hole blocking material (HB), and the hole blocking material (HB) has both a forward peak and a reverse peak at a scan rate of 100 mV / sec when measuring a cyclic voltage current in an oxidation range.

[0015] In yet another exemplary embodiment, the organic material layer includes a blue light-emitting host material (BH), and when the cyclic voltage current is measured, the reversibility value (I r / I f ) is [1.34×(dipole moment)-0.293] or more, and the reversibility value (I r / I f ) is 0.95 or higher.

[0016] In yet another exemplary embodiment, the organic material layer includes a light-emitting host material (EML), and when measuring the cyclic voltage current, the reversibility value (I r / I f) is [0.955-0.1786×(reversibility value in the oxidation range (I r / I f ))] or higher.

[0017] In another exemplary embodiment, the organic material layer including the hole transport material (HT) further includes an electron blocking material (EB) and has a [(HT I r / I f )-(EB I r / I f )] value, HT I r / I f is the reversibility value of the hole transport material (HT) in the oxidation range at a scan rate of 100 mV / s, EB I r / I f is the reversibility value of the electron blocking material (EB) in the oxidation range at a scan rate of 100 mV / sec. In this case, the hole transport material (HT) and the electron blocking material (EB) are contained in different organic material layers, respectively.

[0018] In yet another exemplary embodiment, the organic material layer containing the blue light-emitting dopant material (BD) further contains a blue light-emitting host material (BH) and has a [(LUMO absolute value of the blue light-emitting host material (BH))-(LUMO absolute value of the blue light-emitting dopant material (BD))] value of 0.16 eV to 0.75 eV. In this case, the blue light-emitting dopant material (BD) and the blue light-emitting host material (BH) are contained in the same layer.

[0019] In yet another exemplary embodiment, the organic material layer including the electron transport material (ET) further includes a hole blocking material (HB) and has [LUMO absolute value of the electron transport material (ET) - LUMO absolute value of the hole blocking material (HB)] of 0.05 eV to 0.3 eV. In this case, the electron transport material (ET) and the hole blocking material (HB) are respectively included in different organic material layers.

[0020] In another exemplary embodiment, the organic material layer containing the light-emitting host material (EML) further contains an electron transport material (ET) and has a [(LUMO absolute value of the light-emitting host material (EML))-(LUMO absolute value of the electron transport material (ET))] value of 0.15 eV to 0.35 eV. In this case, the light-emitting host material (EML) and the electron transport material (ET) are respectively contained in different layers, or contained in the same layer.

[0021] Beneficial Effects

[0022] An organic light emitting device according to an exemplary embodiment of the present specification includes a material having excellent electrical stability in the (+) and (-) radical states of an organic light emitting material. The organic light emitting device composed of the material may have a long lifespan characteristic. BRIEF DESCRIPTION OF THE DRAWINGS

[0023] Figure 1 An example of an organic light-emitting device is shown.

[0024] [Explanation of Reference Numerals]

[0025] 101: Base

[0026] 102: Positive electrode

[0027] 103: Organic material layer

[0028] 104: Negative electrode DETAILED DESCRIPTION

[0029] The service life characteristics of an organic light-emitting device are affected by the electrical stability of the (+) radical or (-) radical state of the material for the organic light-emitting device. In the related art, as a method for evaluating the electrical stability of the material for an organic light-emitting device, a method of comparing reduction capacitance using cyclic voltammetry is used. However, this method cannot measure the electrical stability of the (+) radical or (-) radical of the material for an organic light-emitting device.

[0030] The present invention establishes a method for comparing the stability of (+) and (-) free radicals of samples by analyzing the graphical profiles of cyclic voltammograms measured by cyclic voltammetry (CV) in the oxidation range and the reduction range, and provides a method for selecting stable materials for organic light-emitting devices to be applied to the organic material layer of the organic light-emitting device.

[0031] Hereinafter, the present specification will be described in detail.

[0032] In this specification, the cyclic voltammogram is measured by the VSP model. Specifically, the cyclic voltammetry (CV) method is used to measure the current generated by changing the voltage. The voltage of the working electrode increases from the initial voltage (E) at a constant rate (v). i ) starts to change (E=E i -vt, t is time) and measures the current. In this case, v is called the scan rate.

[0033] In this specification, a peak refers to a point in a graph where the sign of the slope changes.

[0034] In the present specification, the height of a peak refers to a value obtained by subtracting a current value of a base line from a current value of a corresponding peak in a cyclic voltammogram.

[0035] In this specification, the current value refers to the absolute value of the current in the cyclic voltammogram.

[0036] In this specification, the forward peak refers to the point where the current magnitude is the largest in the forward scan of the cyclic voltammogram. The increasing current decreases from the forward peak.

[0037] In this specification, the reverse peak refers to the point where the current magnitude is the largest in the reverse scan of the cyclic voltammogram. The increasing current decreases from the reverse peak.

[0038] In this specification, a point where a peak appears in addition to the forward peak and the reverse peak in the cyclic voltammogram is called an impurity peak. The region where the impurity peak appears is not limited to the forward scan or the reverse scan. That is, the impurity peak may appear in the forward scan, may appear in the reverse scan, or may appear in both the forward scan and the reverse scan. There may be one or more impurity peaks.

[0039] In the present specification, the lowest unoccupied molecular orbital (LUMO) and the highest occupied molecular orbital (HOMO) can be obtained by cyclic voltammetry.

[0040] E(HOMO)=[V 溶剂 -(E 开始氧化 -E 1 / 2(溶剂 )eV

[0041] E(LUMO)=[V 溶剂 -(E 开始还原 -E 1 / 2(溶剂) ]eV

[0042] V 溶剂 is the energy level of the solvent, E 1 / 2 is the half-wave energy level of the solvent, E 开始氧化 is the energy level (potential) at the point where oxidation starts, E 开始还原 is the energy level (potential) at the point where reduction starts.

[0043] In addition to cyclic voltammetry (CV), HOMO and LUMO can also be measured using an AC3 instrument and can also be calculated by simulation programs.

[0044] In the present specification, the HOMO or LUMO value to be measured (or calculated) is a value of the measured oxidation potential or reduction potential calibrated by a calibration material ferrocene.

[0045] HOMO = 4.8 - (oxidation potential of ferrocene - oxidation potential of sample)

[0046] LUMO = 4.8 - (oxidation potential of ferrocene - reduction potential of sample)

[0047] In this specification, when HOMO or LUMO is calculated by a simulation program, a Gaussian program or a Schrödinger program may be used as the simulation program. A time-dependent density functional theory (DFT) tool may be used.

[0048] In this specification, the HOMO or LUMO value measured (or calculated) by AC3 is a value obtained by depositing a material on an ITO film and then placing the deposited ITO film in an AC3 apparatus to measure a work function.

[0049] According to an exemplary embodiment of the present specification, as a method of obtaining a cyclic voltammogram, by preparing a sample in which a target compound is dissolved in dimethylformamide (DMF) at a concentration of 0.003 M and heating the sample under N 2 The cyclic voltammograms were obtained under the conditions of gas and electrolyte (TBAC: tert-butyl acetate). In this case, the cyclic voltammograms were fitted by the EC-lab program and measured by the VSP model.

[0050] In this specification, the oxidation range refers to a voltage range in which oxidation can occur.

[0051] In this specification, the reduction range refers to a voltage range in which reduction can occur.

[0052] In this specification, blue refers to a light emission color having a maximum light emission peak of 380 nm to 500 nm.

[0053] In this specification, the dipole moment (DM) (Debye) is calculated using Gaussian 03, a quantum chemical calculation program manufactured by US Gaussian Corporation, and the density functional theory (DFT) is used. For the structure optimized using B3LYP as the functional and 6-31G* as the basis function, the calculated value of the triplet energy is obtained by time-dependent density functional theory (TD-DFT).

[0054] In this specification, "p to q" means greater than or equal to p and less than or equal to q.

[0055] In this specification, it is presumed that the current magnitude of the peak changes within 3% of the reference value when measuring 2 cycles to 10 cycles.

[0056] According to an exemplary embodiment of the present specification, a material suitable for an organic material layer of an organic light emitting device is provided by measuring and analyzing a cyclic voltage and current of an organic light emitting material.

[0057] In an exemplary embodiment of the present specification, the cyclic voltage and current of the organic light emitting material may be measured in an oxidation range or a reduction range.

[0058] In an exemplary embodiment of the present specification, the cyclic voltage current is measured by dissolving the organic light emitting material in an organic solvent in an oxidation range or a reduction range.

[0059] According to an exemplary embodiment of the present specification, the organic solvent is dimethylformamide (DMF).

[0060] In the present specification, reversibility may be quantified as a value of the following Equation 1. Specifically, reversibility at a reference scan rate is defined by the following Equation 1.

[0061] [Equation 1]

[0062] Reversibility = I r / I f

[0063] In equation 1, I r refers to the height of the reverse peak, I f It refers to the height of the positive peak.

[0064] The reference scan rate is the rate at which the profiles can be compared between materials when all corresponding comparison materials have both forward and reverse peaks.

[0065] The height of a peak refers to a value obtained by subtracting a current value in a baseline from a current value of a corresponding peak. Specifically, the height of a peak can be measured by a program for measuring CV.

[0066] In this specification, the oxidation stability is a reversibility value calculated from a cyclic voltammogram obtained in an oxidation range.

[0067] In this specification, the reduction stability is a reversibility value calculated from a cyclic voltammogram obtained in the reduction range.

[0068] A material having high reversible stability in the reduction range (reduction stability) has a stable anion radical state. Therefore, when a material having high reversible stability in the reduction range is used as a dopant material for a blue light-emitting layer, the service life characteristics of an organic light-emitting device can be improved.

[0069] Materials with high reversible stability (oxidation stability) in the oxidation range have a stable cation radical state. Therefore, when a material with high reversible stability in the oxidation range is used as a main body of a blue light-emitting layer, a hole transport layer, an electron blocking layer, an electron transport layer or a hole blocking layer material, the service life characteristics of an organic light-emitting device can be improved.

[0070] The present specification provides an organic light-emitting device including an organic material layer. Specifically, the present specification provides an organic light-emitting device including: a positive electrode; a negative electrode; and an organic material layer disposed between the positive electrode and the negative electrode.

[0071] In an exemplary embodiment of the present specification, the organic material layer includes a hole transport material (HT), and the HOMO absolute value of the hole transport material (HT) is 4.30 eV to 4.60 eV, and when measuring the cyclic voltage current, the reversibility value (I r / I f ) is 0.83 or higher.

[0072] The HOMO absolute value of the hole transport material (HT) is calculated by a simulation program. In an exemplary embodiment, the HOMO absolute value of the hole transport material (HT) is calculated by time-dependent density functional theory (DFT) of the Gaussian program.

[0073] In an exemplary embodiment of the present specification, when measuring the cyclic voltage current, the reversibility value (I r / I f ) is 1.2 or less, preferably 1.0 or less.

[0074] In an exemplary embodiment of the present specification, the hole transport material (HT) is an arylamine compound, a fluorene compound, a spirobifluorene compound, or a carbazole-based compound.

[0075] In an exemplary embodiment of the present specification, the hole transport material (HT) is a compound represented by Formula 1 or 2 below.

[0076] [Formula 1]

[0077]

[0078] [Formula 2]

[0079]

[0080] In equations 1 and 2,

[0081] X1 and X2 are each hydrogen or deuterium, or are directly single-bonded to each other to form a ring,

[0082] R11 to R14, R21 and R22 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amino group; or a substituted or unsubstituted aryl group, or may each be bonded to an adjacent group to form a substituted or unsubstituted ring,

[0083] L11 and L21 to L23 are the same as or different from each other and are each independently a single bond; or a substituted or unsubstituted arylene group,

[0084] Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; a substituted or unsubstituted silyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0085] r11, r13, r14, r21 and r22 are each an integer from 0 to 4, and r12 is an integer from 0 to 3, and

[0086] When r11 to r14, r21 and r22 are 2 or more, the substituents in the brackets are the same as or different from each other.

[0087] In an exemplary embodiment of the present specification, when X1 and X2 are directly single-bonded to each other to form a ring, the core of Formula 1 includes spirobifluorene.

[0088] In an exemplary embodiment of the present specification, R11 to R14 are the same as or different from each other, and are each independently hydrogen; deuterium; an alkyl group having 1 to 6 carbon atoms; or an aryl group having 6 to 30 carbon atoms.

[0089] In an exemplary embodiment of the present specification, R11 to R14 are the same as or different from each other, and are each independently hydrogen; deuterium; methyl; ethyl; propyl; tert-butyl; phenyl; biphenyl; or naphthyl.

[0090] In an exemplary embodiment of the present specification, L11 is a single bond; or an arylene group having 6 to 30 carbon atoms.

[0091] In an exemplary embodiment of the present specification, L11 is a single bond; a phenylene group; a biphenylene group; or a naphthylene group.

[0092] In an exemplary embodiment of the present specification, Ar11 and Ar12 are the same as or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; or a heteroaryl group having 2 to 30 carbon atoms.

[0093] In an exemplary embodiment of the present specification, Ar11 and Ar12 are each the same as or different from each other, and are each independently a phenyl group which is unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms; a biphenyl group which is unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms; a terphenyl group which is unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms; a naphthyl group which is unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms; a fluorenyl group which is unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms; a dibenzofuranyl group; or a dibenzothiophenyl group.

[0094] In an exemplary embodiment of the present specification, Ar11 and Ar12 are the same as or different from each other, and are each independently a phenyl group; a biphenyl group; a terphenyl group; a naphthyl group; a dibenzofuranyl group; or a dibenzothienyl group.

[0095] In an exemplary embodiment of the present specification, L21 to L23 are the same as or different from each other, and are each independently a single bond; or an arylene group having 6 to 30 carbon atoms.

[0096] In an exemplary embodiment of the present specification, L21 to L23 are the same as or different from each other, and are each independently a single bond; a phenylene group; a biphenylene group; a terphenylene group; or a naphthylene group.

[0097] In an exemplary embodiment of the present specification, L22 and L23 are the same as or different from each other, and are each independently a single bond; a phenylene group; a biphenylene group; a terphenylene group; or a naphthylene group.

[0098] In an exemplary embodiment of the present specification, L21 is a phenylene group; a biphenylene group; a terphenylene group; or a naphthylene group.

[0099] In an exemplary embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a nitro group; an alkylsilyl group having 1 to 30 carbon atoms; an arylsilyl group having 6 to 90 carbon atoms; a cycloalkyl group having 3 to 10 carbon atoms; an aryl group having 6 to 30 carbon atoms; or a heteroaryl group having 2 to 30 carbon atoms.

[0100] In an exemplary embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other and are each independently a cyano group; an alkylsilyl group having 1 to 15 carbon atoms; an arylsilyl group having 6 to 50 carbon atoms; a cycloalkyl group having 3 to 10 carbon atoms; an aryl group having 6 to 30 carbon atoms; or a heteroaryl group having 2 to 30 carbon atoms.

[0101] In an exemplary embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and are each independently a phenyl group; a biphenyl group; a terphenyl group; a naphthyl group; a dibenzofuranyl group; or a dibenzothienyl group.

[0102] In an exemplary embodiment of the present specification, R21 and R22 are the same as or different from each other, and are each independently hydrogen; or deuterium, or may each bond with an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring.

[0103] In an exemplary embodiment of the present specification, R21 and R22 are the same as or different from each other, and are each independently hydrogen; or deuterium, or may each bond with an adjacent group to form a benzene ring.

[0104] In an exemplary embodiment of the present specification, the hole transport material (HT) is selected from the following compounds.

[0105]

[0106] In an exemplary embodiment of the present specification, the organic material layer includes an electron blocking material (EB), and when measuring the cyclic voltage current, the reversibility value (I r / I f ) is greater than 0.5.

[0107] In an exemplary embodiment of the present specification, when measuring the cyclic voltage current, the reversibility value (I r / I f ) is 0.7 or higher, preferably 0.9 or higher.

[0108] In an exemplary embodiment of the present specification, when measuring the cyclic voltage current, the reversibility value (I r / I f ) is 1.2 or less, preferably 1.0 or less.

[0109] In an exemplary embodiment of the present specification, the electron blocking material (EB) has a HOMO absolute value of 5.23 eV to 5.42 eV.

[0110] The HOMO absolute value of the electron blocking material (EB) is calculated by a simulation program. In an exemplary embodiment, the HOMO absolute value of the electron blocking material (EB) is calculated by time-dependent density functional theory (DFT) of a Gaussian program.

[0111] In an exemplary embodiment of the present specification, the electron blocking material (EB) is an arylamine compound or a carbazole-based compound.

[0112] In an exemplary embodiment of the present specification, the electron blocking material (EB) is a compound represented by Formula 1 or 2.

[0113] In an exemplary embodiment of the present specification, Formulae 1 and 2 of the electron blocking material (EB) are the same as those described in Formulae 1 and 2 of the hole transport material (HT).

[0114] In an exemplary embodiment of the present specification, the electron blocking material (EB) is selected from the following compounds.

[0115]

[0116] The present specification provides an organic light-emitting device comprising the above-mentioned hole transport material (HT) and the electron blocking material (EB). Specifically, the organic light-emitting device comprises an organic material layer, and the organic material layer comprises a hole transport layer and an electron blocking layer. The hole transport layer comprises the above-mentioned hole transport material (HT), and the electron blocking layer comprises the above-mentioned electron blocking material (EB). In this case, (HT I r / I f )-(EB I r / I f ) is 0.15 or less, HT I r / I f is the reversibility value of the hole transport material (HT) in the oxidation range at a scan rate of 100 mV / s, EB I r / I f is the reversibility value of the electron blocking material (EB) in the oxidation range at a scan rate of 100 mV / sec. The organic material layer includes a light-emitting layer, the electron blocking layer is adjacent to the light-emitting layer, and the hole transport layer is adjacent to the positive electrode. The electron blocking layer and the hole transport layer may be in direct contact with each other.

[0117] In an exemplary embodiment of the present specification, (HT I r / I f )-(EB I r / I f ) has a value of -0.17 or higher. In another exemplary embodiment, (HT I r / I f )-(EB I r / I f ) has a value of -0.12 or higher. In yet another exemplary embodiment, (HT I r / I f )-(EB I r / I f ) has a value of -0.10 or higher. In yet another exemplary embodiment, (HT I r / I f )-(EB I r / I f ) has a value of 0 or higher.

[0118] In an exemplary embodiment of the present specification, (HT I r / I f )-(EB I r / I f ) has a value of 0.1 or less. In another exemplary embodiment, (HT I r / I f )-(EB I r / I f ) has a value of 0.1 or less. In yet another exemplary embodiment, (HT I r / I f )-(EB I r / I f ) is 0.06 or less.

[0119] In an exemplary embodiment of the present specification, the organic material layer includes a blue light-emitting dopant material (BD), and the LUMO absolute value of the blue light-emitting dopant material (BD) is 2.40 eV to 2.74 eV, and when measuring the cyclic voltage current, the reversibility value (I r / I f ) is greater than [-23.14+8.458×(LUMO absolute value)].

[0120] The LUMO absolute value of the blue light emitting dopant material (BD) is measured by AC3. In an exemplary embodiment, the LUMO absolute value of the blue light emitting dopant material (BD) is a work function value measured by an AC3 device.

[0121] In an exemplary embodiment of the present specification, the LUMO absolute value of the blue light-emitting dopant material (BD) is 2.40 eV to 2.74 eV when measured by AC3. In an exemplary embodiment, the reversibility value (I r / I f ) is greater than [-23.14+8.458×(AC3 LUMO absolute value)]. In this case, the stability of the blue light-emitting dopant material (BD) is enhanced. Therefore, the lifespan characteristics of the organic light-emitting device are improved.

[0122] In an exemplary embodiment of the present specification, the blue light-emitting dopant material (BD) is an arylamine compound, a pyrene compound, a fluorene compound, or a boron polycyclic compound.

[0123] In an exemplary embodiment of the present specification, the blue light-emitting dopant material (BD) is a compound represented by any one of the following Formulae 3 to 6.

[0124] [Formula 3]

[0125]

[0126] [Formula 4]

[0127]

[0128] [Formula 5]

[0129]

[0130] [Formula 6]

[0131]

[0132] In equations 3 to 6,

[0133] R31 and R32 are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted silyl; or substituted or unsubstituted aryl,

[0134] X3 and X4 are each hydrogen or deuterium, or are directly single-bonded to each other to form a ring,

[0135] R41 and R42 are the same as or different from each other and are each independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group,

[0136] R43 to R46 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or adjacent substituents are bonded to each other to form a substituted or unsubstituted ring,

[0137] Ar31 to Ar34 and Ar41 to Ar44 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0138] A1 to A6 are the same as or different from each other, and are each independently a monocyclic to polycyclic aromatic hydrocarbon ring; or a monocyclic to polycyclic aromatic heterocyclic ring,

[0139] R51 to R53 and R61 to R63 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amino group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or bond with an adjacent substituent to form a substituted or unsubstituted aromatic ring; or a substituted or unsubstituted aliphatic ring,

[0140] Y1 is B or N,

[0141] Y2 is O, S or N(Ar63)(Ar64),

[0142] Y3 is O, S or N(Ar65)(Ar66),

[0143] Y4 is C or Si,

[0144] Ar51, Ar52, and Ar61 to Ar66 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or are bonded with an adjacent substituent to form a substituted or unsubstituted aromatic ring; or a substituted or unsubstituted aliphatic ring, and

[0145] R41, R42, R51 to R53 and R61 to R63 are each an integer of 0 to 4, and when R41, R42, R51 to R53 and R61 to R63 are 2 or more, the substituents in brackets are the same as or different from each other.

[0146] In an exemplary embodiment of the present specification, R31 and R32 are the same as or different from each other and are each independently hydrogen; deuterium; an alkyl group having 1 to 6 carbon atoms; an alkylsilyl group having 1 to 10 carbon atoms; an arylsilyl group having 6 to 50 carbon atoms; or an aryl group having 6 to 30 carbon atoms.

[0147] In an exemplary embodiment of the present specification, R31 and R32 are the same as or different from each other, and are each independently hydrogen; deuterium; methyl; ethyl; propyl; isopropyl; tert-butyl; trimethylsilyl; triphenylsilyl; phenyl; biphenyl; or naphthyl.

[0148] In an exemplary embodiment of the present specification, Ar31 to Ar34 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0149] In an exemplary embodiment of the present specification, Ar31 to Ar34 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; a naphthyl group; a dibenzofuranyl group; or a dibenzothienyl group.

[0150] In an exemplary embodiment of the present specification, when X3 and X4 are directly single-bonded to each other to form a ring, the core of Formula 4 includes spirobifluorene.

[0151] In an exemplary embodiment of the present specification, R41 and R42 are the same as or different from each other, and are each independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

[0152] In an exemplary embodiment of the present specification, R43 to R46 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or adjacent substituents are bonded to each other to form a pentagonal heterocyclic ring in which a substituted or unsubstituted aromatic ring is fused.

[0153] In an exemplary embodiment of the present specification, R43 to R46 are the same as or different from each other and are each independently hydrogen; or one or more substituents selected from the group consisting of deuterium, alkyl groups having 1 to 6 carbon atoms, and aryl groups having 6 to 30 carbon atoms, or substituents in which two or more substituents selected from the group are connected.

[0154] In an exemplary embodiment of the present specification, R43 and R44 are bonded to each other to form a substituted or unsubstituted benzofuran ring or a substituted or unsubstituted benzothiophene ring.

[0155] In an exemplary embodiment of the present specification, R45 and R46 are bonded to each other to form a substituted or unsubstituted benzofuran ring or a substituted or unsubstituted benzothiophene ring.

[0156] In an exemplary embodiment of the present specification, Ar41 to Ar44 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0157] In an exemplary embodiment of the present specification, Ar41 to Ar44 are the same as or different from each other, and are each independently an unsubstituted or tert-butyl-substituted phenyl group; a naphthyl group; a dibenzofuranyl group; or a dibenzothienyl group.

[0158] In an exemplary embodiment of the present specification, A1 to A6 are the same as or different from each other, and are each independently a monocyclic to polycyclic aromatic hydrocarbon ring; or a monocyclic to polycyclic aromatic heterocyclic ring.

[0159] In an exemplary embodiment of the present specification, A1 to A6 are the same as or different from each other, and are each independently a monocyclic to bicyclic aromatic hydrocarbon ring; or a monocyclic to bicyclic aromatic heterocyclic ring containing O or S.

[0160] In an exemplary embodiment of the present specification, A1 to A6 are the same as or different from each other, and are each independently a benzene ring; or a thiophene ring.

[0161] In an exemplary embodiment of the present specification, A1 to A6 are each a benzene ring.

[0162] In an exemplary embodiment of the present specification, R51 to R53 and R61 to R63 are the same as or different from each other and are each independently hydrogen; or one or more substituents selected from the group consisting of deuterium, an alkyl group having 1 to 6 carbon atoms, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 50 carbon atoms, an alkylamine group having 1 to 30 carbon atoms, an alkylarylamine group having 1 to 50 carbon atoms, an arylamine group having 6 to 50 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heteroaryl group having 2 to 30 carbon atoms, or a substituent in which two or more substituents selected from the group are connected, or adjacent substituents are bonded to each other to form an unsubstituted or substituent-substituted aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

[0163] In an exemplary embodiment of the present specification, R53 and R63 are the same as or different from each other, and are each independently a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms; a substituted or unsubstituted alkylarylamine group having 1 to 50 carbon atoms; or a substituted or unsubstituted arylamine group having 6 to 50 carbon atoms.

[0164] In an exemplary embodiment of the present specification, Ar51, Ar52 and Ar61 to Ar66 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0165] In an exemplary embodiment of the present specification, Ar51, Ar52 and Ar61 to Ar66 are the same as or different from each other, and are each independently an unsubstituted or aryl-substituted alkyl group having 1 to 10 carbon atoms; an unsubstituted or aryl-substituted aryl group having 6 to 30 carbon atoms; or a heteroaryl group having 2 to 30 carbon atoms.

[0166] In an exemplary embodiment of the present specification, Ar51, Ar52, and Ar61 to Ar66 are the same as or different from each other, and are each independently a phenyl group; a biphenyl group; a naphthyl group; a dimethylfluorenyl group; a diphenylfluorenyl group; a dibenzofuranyl group; or a dibenzothiophenyl group.

[0167] In an exemplary embodiment of the present specification, R51 and Ar51 are bonded to each other to form a substituted or unsubstituted aromatic ring; or a substituted or unsubstituted aliphatic ring.

[0168] In an exemplary embodiment of the present specification, R52 and Ar52 are bonded to each other to form a substituted or unsubstituted aromatic ring; or a substituted or unsubstituted aliphatic ring.

[0169] In an exemplary embodiment of the present specification, R51 and Ar51 are bonded to each other to form a substituted or unsubstituted monocyclic to polycyclic aromatic hydrocarbon ring; or a substituted or unsubstituted monocyclic to polycyclic aliphatic hydrocarbon ring.

[0170] In an exemplary embodiment of the present specification, R52 and Ar52 are bonded to each other to form a substituted or unsubstituted monocyclic to polycyclic aromatic hydrocarbon ring; or a substituted or unsubstituted monocyclic to polycyclic aliphatic hydrocarbon ring.

[0171] In an exemplary embodiment of the present specification, R51 and Ar51 are bonded to each other to form a substituted or unsubstituted benzene ring; a substituted or unsubstituted cyclohexane ring; or a substituted or unsubstituted cyclopentane ring.

[0172] In an exemplary embodiment of the present specification, R52 and Ar52 are bonded to each other to form a substituted or unsubstituted benzene ring; a substituted or unsubstituted cyclohexane ring; or a substituted or unsubstituted cyclopentane ring.

[0173] In an exemplary embodiment of the present specification, the blue light-emitting dopant material (BD) is selected from the following compounds.

[0174]

[0175] In an exemplary embodiment of the present specification, the organic material layer includes a blue light-emitting host material (BH), and when measuring the cyclic voltage current, the reversibility value (I r / I f ) is [1.34×(dipole moment)-0.293] or more, and the reversibility value (I r / I f ) is 0.95 or higher.

[0176] In an exemplary embodiment of the present specification, when measuring the cyclic voltage current, the reversibility value (I r / I f ) is 0.95 or higher, preferably 0.96 or higher, and more preferably 0.97 or higher.

[0177] In an exemplary embodiment of the present specification, when measuring the cyclic voltage current, the reversibility value (I r / I f ) is 1.2 or less, preferably 1.1 or less.

[0178] In an exemplary embodiment of the present specification, the blue light-emitting host material (BH) is a compound represented by the following formula H. Specifically, the blue light-emitting host material (BH) and the blue light-emitting dopant material are used in the same organic material layer.

[0179] [Formula H]

[0180]

[0181] In formula H,

[0182] L101 to L103 are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0183] R101 to R107 are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted silyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl,

[0184] Ar101 to Ar103 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0185] a is 0 or 1.

[0186] In an exemplary embodiment of the present specification, when a is 0, hydrogen or deuterium is linked to the position of -L103-Ar103.

[0187] In an exemplary embodiment of the present specification, L101 to L103 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms and containing N, O or S.

[0188] In an exemplary embodiment of the present specification, L101 to L103 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted divalent dibenzofuranyl group; or a substituted or unsubstituted divalent dibenzothienyl group.

[0189] In an exemplary embodiment of the present specification, L101 to L103 are the same as or different from each other, and are each independently a direct bond; a phenylene group; a biphenylene group; a naphthylene group; or a phenanthrylene group.

[0190] In an exemplary embodiment of the present specification, Ar101 to Ar103 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0191] In an exemplary embodiment of the present specification, Ar101 to Ar103 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted terphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted anthracenyl; a substituted or unsubstituted phenanthrenyl; a substituted or unsubstituted phenanthrenyl; a substituted or unsubstituted fluorenyl; a substituted or unsubstituted benzofluorenyl; a substituted or unsubstituted furanyl; a substituted or unsubstituted thienyl; a substituted or unsubstituted dibenzofuranyl; a substituted or unsubstituted naphthobenzofuranyl; a substituted or unsubstituted dibenzothienyl; or a substituted or unsubstituted naphthobenzothienyl.

[0192] In an exemplary embodiment of the present specification, Ar101 to Ar103 are the same as or different from each other, and are each independently a phenyl group; a biphenyl group; a naphthyl group; a phenanthrenyl group; a dibenzofuranyl group; or a dibenzothienyl group.

[0193] In an exemplary embodiment of the present specification, R101 to R107 are hydrogen or deuterium.

[0194] In an exemplary embodiment of the present specification, Formula H is any one selected from the following compounds.

[0195]

[0196] In an exemplary embodiment of the present specification, the organic material layer containing a blue light-emitting dopant material (BD) also contains a blue light-emitting host material (BH) and has a [(LUMO absolute value of the blue light-emitting host material (BH))-(LUMO absolute value of the blue light-emitting dopant material (BD))] value of 0.16eV to 0.75eV.

[0197] The LUMO absolute value of the blue light emitting host material (BH) is measured by AC3. In an exemplary embodiment, the LUMO absolute value of the blue light emitting host material (BH) is a work function value measured by an AC3 device.

[0198] In an exemplary embodiment of the present specification, [LUMO absolute value of the blue light-emitting host material (BH)] - [LUMO absolute value of the blue light-emitting dopant material (BD)] is 0.18 eV or higher, preferably 0.20 eV or higher.

[0199] In an exemplary embodiment of the present specification, [LUMO absolute value of the blue light-emitting host material (BH)] - [LUMO absolute value of the blue light-emitting dopant material (BD)] is 0.65 eV or less, preferably 0.60 eV or less.

[0200] The organic material layer according to an exemplary embodiment of the present specification includes a blue light emitting layer including a compound represented by any one of Formulae 3 to 6 as a dopant of the light emitting layer and a compound represented by Formula H as a host of the light emitting layer.

[0201] In an exemplary embodiment of the present specification, the content of the compound represented by any one of Formulae 3 to 6 is 0.01 to 30 parts by weight; 0.1 to 20 parts by weight; or 0.5 to 10 parts by weight, based on 100 parts by weight of the compound represented by Formula H.

[0202] In an exemplary embodiment of the present specification, the organic material layer includes an electron transport material (ET), and the LUMO absolute value of the electron transport material (ET) is 2.60 eV to 2.90 eV, and when measuring the cyclic voltage current, the reversibility value (I r / If ) is greater than [4.96-1.535×(LUMO absolute value)].

[0203] The LUMO absolute value of the electron transport material (ET) is measured by AC3. In an exemplary embodiment, the LUMO absolute value of the electron transport material (ET) is a work function value measured by an AC3 device.

[0204] In an exemplary embodiment of the present specification, the electron transport material (ET) is a triazine-based or pyrimidine-based compound.

[0205] In an exemplary embodiment of the present specification, the electron transport material (ET) is represented by Formula 8 below.

[0206] [Formula 8]

[0207]

[0208] In formula 8,

[0209] At least one of Z1 to Z3 is N, and the rest are CH,

[0210] L81 to L83 are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0211] Ar81 and Ar82 are the same as or different from each other and are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0212] G1 is a monovalent substituent represented by any one of the following formulae 801 to 804,

[0213]

[0214]

[0215] [Formula 804]

[0216]

[0217] In equations 801 to 804,

[0218] Any carbon is connected to L83 of Formula 8,

[0219] Y5 is O or S,

[0220] L84 is a substituted or unsubstituted arylene group, and

[0221] R81 to R83 are the same as or different from each other, and are each independently hydrogen; deuterium; cyano; aryl; or aryl substituted with cyano.

[0222] In an exemplary embodiment of the present specification, the electron transport material (ET) is represented by Formula 12 below.

[0223] [Formula 12]

[0224]

[0225] In formula 12,

[0226] Het is a substituted or unsubstituted N-containing heteroaryl group,

[0227] Ar112 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted aryl group, and

[0228] L121 is a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group.

[0229] In an exemplary embodiment of the present specification, Z1 to Z3 are all N.

[0230] In an exemplary embodiment of the present specification, Z1 and Z2 are N, and Z3 is CH.

[0231] In an exemplary embodiment of the present specification, L81 to L84 and L121 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms and containing N, O or S.

[0232] In an exemplary embodiment of the present specification, L81 to L84 and L121 are the same as or different from each other, and are each independently a direct bond; a phenylene group; or a naphthylene group.

[0233] In an exemplary embodiment of the present specification, L81 to L83 and L121 are the same as or different from each other, and are each independently a direct bond; or a phenylene group.

[0234] In an exemplary embodiment of the present specification, L84 is a direct bond; a phenylene group; or a naphthylene group.

[0235] In an exemplary embodiment of the present specification, Ar81 and Ar82 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0236] In an exemplary embodiment of the present specification, Ar81 and Ar82 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted triazine group; or a substituted or unsubstituted pyridyl group.

[0237] In an exemplary embodiment of the present specification, G1 is any one selected from the following structures.

[0238]

[0239] In the structure, the definitions of L84 and R81 to R83 are the same as those described above.

[0240] In an exemplary embodiment of the present specification, R81 to R83 are the same as or different from each other, and are each independently hydrogen; deuterium; a cyano group; an aryl group having 6 to 30 carbon atoms; an aryl group having 6 to 30 carbon atoms substituted with a cyano group.

[0241] In an exemplary embodiment of the present specification, R81 to R83 are the same as or different from each other, and are each independently hydrogen; deuterium; cyano; phenyl; or phenyl substituted with cyano.

[0242] In an exemplary embodiment of the present specification, Het is a substituted or unsubstituted N-containing heteroaryl group having 2 to 20 carbon atoms.

[0243] In an exemplary embodiment of the present specification, Het is an N-containing heteroaryl group having 2 to 20 carbon atoms that is unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms.

[0244] In an exemplary embodiment of the present specification, Het is an unsubstituted or ethyl-substituted benzimidazolyl group.

[0245] In an exemplary embodiment of the present specification, the electron transport material (ET) is selected from the following compounds.

[0246]

[0247] In an exemplary embodiment of the present specification, the organic material layer includes a hole blocking material (HB), and when a cyclic voltage current is measured in an oxidation range, the hole blocking material (HB) has both a forward peak and a reverse peak at a scan rate of 100 mV / sec.

[0248] In an exemplary embodiment of the present specification, the hole blocking material (HB) is a triazine-based or pyrimidine-based compound.

[0249] In an exemplary embodiment of the present specification, the hole blocking material (HB) is represented by Formula 9 below.

[0250] [Formula 9]

[0251]

[0252] In formula 9,

[0253] At least one of Z4 to Z6 is N, and the rest are CH,

[0254] L85 to L87 are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0255] Ar83 and Ar84 are the same as or different from each other and are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0256] G2 is a monovalent substituent represented by the following formula 901,

[0257] [Formula 901]

[0258]

[0259] In formula 901,

[0260] Any carbon is connected to L87 of Formula 9,

[0261] Y6 is O or S, and

[0262] R84 is hydrogen; deuterium; cyano; aryl; or aryl substituted with cyano.

[0263] In an exemplary embodiment of the present specification, Z4 to Z6 are all N.

[0264] In an exemplary embodiment of the present specification, Z4 and Z5 are N, and Z6 is CH.

[0265] In an exemplary embodiment of the present specification, L85 to L87 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms and containing N, O or S.

[0266] In an exemplary embodiment of the present specification, L85 to L87 are the same as or different from each other, and are each independently a direct bond; a phenylene group; or a biphenylene group.

[0267] In an exemplary embodiment of the present specification, Ar83 and Ar84 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0268] In an exemplary embodiment of the present specification, Ar83 and Ar84 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted pyridyl group.

[0269] In an exemplary embodiment of the present specification, Ar83 and Ar84 are the same as or different from each other, and are each independently a phenyl group; a biphenyl group; a terphenyl group; or a naphthyl group.

[0270] In an exemplary embodiment of the present specification, G2 is any one selected from the following structures.

[0271]

[0272] In the structure described above, the definition of R84 is the same as that described above.

[0273] In an exemplary embodiment of the present specification, R84 is hydrogen; deuterium; a cyano group; an aryl group having 6 to 30 carbon atoms; or an aryl group having 6 to 30 carbon atoms substituted with a cyano group.

[0274] In an exemplary embodiment of the present specification, R84 are the same as or different from each other, and are each independently hydrogen; deuterium; cyano; phenyl; or phenyl substituted with cyano.

[0275] In an exemplary embodiment of the present specification, the hole blocking material (HB) is represented by Formula 12.

[0276] In an exemplary embodiment of the present specification, the hole blocking material (HB) is represented by the following Formula 11.

[0277] [Formula 11]

[0278]

[0279] In formula 11,

[0280] Ar111 is substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl, and

[0281] Ar112 is a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group.

[0282] In an exemplary embodiment of the present specification, Ar111 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0283] In an exemplary embodiment of the present specification, Ar111 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0284] In an exemplary embodiment of the present specification, Ar111 is a phenyl group.

[0285] In an exemplary embodiment of the present specification, Ar112 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0286] In an exemplary embodiment of the present specification, Ar112 is an arylene group having 6 to 20 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms.

[0287] In an exemplary embodiment of the present specification, Ar112 is a dimethylfluorenylene group.

[0288] In an exemplary embodiment of the present specification, the hole blocking material (HB) is selected from the following compounds.

[0289]

[0290] This specification provides an organic light-emitting device comprising the above-mentioned electron transport material (ET) and hole blocking material (HB). Specifically, the organic light-emitting device includes an organic material layer, and the organic material layer includes an electron transport layer and a hole blocking layer. The electron transport layer includes the above-mentioned electron transport material (ET), and the hole blocking layer includes the above-mentioned hole blocking material (HB). In this case, [LUMO absolute value of electron transport material (ET) -LUMO absolute value of hole blocking material (HB)] is 0.05eV to 0.3eV. The organic material layer includes a light-emitting layer, the hole blocking layer is adjacent to the light-emitting layer, and the electron transport layer is adjacent to the negative electrode. The hole blocking layer and the electron transport layer may be in direct contact with each other.

[0291] The LUMO absolute value of the electron transport material (ET) and the LUMO absolute value of the hole blocking material (HB) are values ​​measured by AC3. Specifically, the LUMO absolute value of the electron transport material (ET) and the LUMO absolute value of the hole blocking material (HB) are work function values ​​measured by AC3 equipment.

[0292] In an exemplary embodiment of the present specification, the organic material layer includes a light-emitting host material (EML), and when measuring the cyclic voltage current, the reversibility value (I r / If ) is [0.955-0.1786×(reversibility value in oxidation range (I r / I f ))] or higher.

[0293] In an exemplary embodiment of the present specification, the light-emitting host material (EML) is a compound including triazine and indolocarbazole.

[0294] In an exemplary embodiment of the present specification, the light-emitting host material (EML) is represented by Formula 10 below.

[0295] [Formula 10]

[0296]

[0297] In formula 10,

[0298] At least one of X91 to X93 is N, and the rest are CH,

[0299] L91 and L92 are the same as or different from each other and are each independently a direct bond; or a substituted or unsubstituted arylene group, and

[0300] Ar91 to Ar93 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0301] In an exemplary embodiment of the present specification, X91 to X93 are all N.

[0302] In an exemplary embodiment of the present specification, X91 and X92 are N, and X93 is CH.

[0303] In an exemplary embodiment of the present specification, L91 and L92 are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms and containing N, O or S.

[0304] In an exemplary embodiment of the present specification, L91 and L92 are the same as or different from each other, and are each independently a direct bond; or an unsubstituted or cyano-substituted arylene group having 6 to 30 carbon atoms.

[0305] In an exemplary embodiment of the present specification, L91 and L92 are the same as or different from each other, and are each independently a direct bond; an unsubstituted or cyano-substituted phenylene group; or an unsubstituted or cyano-substituted naphthylene group.

[0306] In an exemplary embodiment of the present specification, Ar91 to Ar93 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0307] In an exemplary embodiment of the present specification, Ar91 to Ar93 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothienyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted triazine group; or a substituted or unsubstituted pyridyl group.

[0308] In an exemplary embodiment of the present specification, Ar91 to Ar93 are the same as or different from each other, and are each independently a phenyl group; a biphenyl group; a terphenyl group; a naphthyl group; a dibenzofuranyl group; or a dibenzothienyl group, and are unsubstituted or deuterium-substituted.

[0309] In an exemplary embodiment of the present specification, Formula 10 is represented by any one of the following Formulae 10-1 to 10-7.

[0310]

[0311]

[0312]

[0313] In Formulae 10-1 to 10-7, definitions of X91 to X93, Ar91 to Ar93, L91 and L92 are the same as those defined in Formula 10, and X99 is O or S.

[0314] In an exemplary embodiment of the present specification, the light-emitting host material (EML) is selected from the following compounds.

[0315]

[0316] In an exemplary embodiment of the present specification, the organic material layer including the light-emitting host material (EML) is the light-emitting layer. The light-emitting region of the light-emitting layer is green. That is, the light-emitting layer including the light-emitting host material (EML) has a maximum light-emitting peak of 495nm to 570nm.

[0317] In another exemplary embodiment, the organic material layer including the hole transport material (HT) further includes an electron blocking material (EB) and has a [(HT I r / I f )-(EB Ir / I f )] value, HT I r / I f is the reversibility value of the hole transport material (HT) in the oxidation range at a scan rate of 100 mV / s, EB I r / I f is the reversibility value of the electron blocking material (EB) in the oxidation range at a scan rate of 100 mV / sec. In this case, the hole transport material (HT) and the electron blocking material (EB) are each contained in a different organic material layer, the organic material layer containing the electron blocking material (EB) is adjacent to the light emitting layer, and the organic material layer containing the hole transport material (HT) is adjacent to the positive electrode. In an exemplary embodiment, the organic material layer containing the electron blocking material (EB) and the organic material layer containing the hole transport material (HT) are in direct contact with each other.

[0318] In yet another exemplary embodiment, the organic material layer containing the blue light-emitting dopant material (BD) further contains a blue light-emitting host material (BH) and has a [(LUMO absolute value of the blue light-emitting host material (BH))-(LUMO absolute value of the blue light-emitting dopant material (BD))] value of 0.16 eV to 0.75 eV. In this case, the blue light-emitting dopant material (BD) and the blue light-emitting host material (BH) are contained in the same layer.

[0319] In yet another exemplary embodiment, the organic material layer containing the electron transport material (ET) further contains a hole blocking material (HB) and has a [LUMO absolute value of the electron transport material (ET) - LUMO absolute value of the hole blocking material (HB)] of 0.05 eV to 0.3 eV. In this case, the electron transport material (ET) and the hole blocking material (HB) are each contained in a different organic material layer, the organic material layer containing the hole blocking material (HB) is adjacent to the light emitting layer, and the organic material layer containing the electron transport material (ET) is adjacent to the negative electrode. In an exemplary embodiment, the organic material layer containing the hole blocking material (HB) and the organic material layer containing the electron transport material (ET) are in direct contact with each other.

[0320] In another exemplary embodiment, the organic material layer containing the light-emitting host material (EML) further contains an electron transport material (ET) and has a [(LUMO absolute value of the light-emitting host material (EML))-(LUMO absolute value of the electron transport material (ET))] value of 0.15eV to 0.35eV. In this case, the light-emitting host material (EML) and the electron transport material (ET) are each contained in a different organic material layer, the organic material layer containing the light-emitting host material (EML) is the light-emitting layer, and the organic material layer containing the electron transport material (ET) is disposed between the light-emitting layer and the negative electrode. In an exemplary embodiment, the light-emitting layer and the organic material layer containing the electron transport material (ET) are in direct contact with each other.

[0321] The organic material layer of the organic light-emitting device of the present specification may be composed of a single-layer structure, but may also be composed of a multilayer structure in which an organic material layer having two or more layers is stacked. In addition, the organic light-emitting device of the present application may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. as an organic material layer. However, the structure of the organic light-emitting device is not limited thereto, and may include a greater or lesser number of organic layers.

[0322] In an exemplary embodiment of the present specification, the organic light emitting device further includes one layer or two or more layers selected from a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0323] In an exemplary embodiment of the present specification, the hole transport layer includes a hole transport material (HT), and is disposed between the positive electrode and the light emitting layer.

[0324] In an exemplary embodiment of the present specification, the electron blocking layer includes an electron blocking material (EB), and is disposed between the positive electrode and the light emitting layer.

[0325] In an exemplary embodiment of the present specification, the blue light-emitting layer includes a blue light-emitting dopant material (BD) and a blue light-emitting host material (BH).

[0326] In an exemplary embodiment of the present specification, the green light emitting layer includes a light emitting host material (EML). In this case, the light emitting layer may further include a dopant, and the dopant is a phosphorescent dopant or a fluorescent dopant.

[0327] In an exemplary embodiment of the present specification, the hole blocking layer includes a hole blocking material (HB), and is disposed between the negative electrode and the light emitting layer.

[0328] In an exemplary embodiment of the present specification, the electron transport layer includes an electron transport material (ET), and is disposed between the negative electrode and the light emitting layer.

[0329] In an exemplary embodiment of the present specification, the hole transport layer is a single layer of a hole transport material (HT), or other organic compounds are mixed and used.

[0330] In an exemplary embodiment of the present specification, the electron blocking layer is a single layer of an electron blocking material (EB), or other organic compounds are mixed and used.

[0331] In an exemplary embodiment of the present specification, the light emitting layer includes only the blue light emitting dopant material (BD) and the compound represented by Formula H, or other organic compounds are mixed and used.

[0332] In an exemplary embodiment of the present specification, the blue light emitting layer includes only a blue light emitting dopant material (BD) and a blue light emitting host material (BH), or other organic compounds are mixed and used.

[0333] In an exemplary embodiment of the present specification, the green light emitting layer includes only a light emitting host material (EML) and a dopant, or other organic compounds are mixed and used.

[0334] In an exemplary embodiment of the present specification, the hole blocking layer is a single layer of a hole blocking material (HB), or other organic compounds are mixed and used.

[0335] In an exemplary embodiment of the present specification, the electron transport layer is a single layer of an electron transport material (ET), or other organic compounds are mixed and used.

[0336] Figure 1 The structure of the organic light emitting device according to the present invention is illustrated in that a substrate 101, a positive electrode 102, an organic material layer 103, and a negative electrode 104 are sequentially stacked.

[0337] Embodiments of the invention

[0338] Hereinafter, this specification will be described in detail with reference to the embodiments for specifically describing this specification. However, the embodiments according to this specification can be modified into various forms, and should not be interpreted as the scope of the present application being limited to the embodiments described in detail below. The embodiments of the present application are provided to more completely illustrate this specification to those of ordinary skill in the art.

[0339] -Reversibility (I r / I f )

[0340] Samples in which the compounds were each dissolved in dimethylformamide (DMF) were prepared to obtain cyclic voltammograms at 1 to 3 scan rates selected from 10 mV / sec, 50 mV / sec, 100 mV / sec, 300 mV / sec, and 500 mV / sec in the oxidation range or the reduction range. Electrolyte tert-butyl acetate (TBAC) was used as the electrolyte, the EC-lab program was used, and the VSP model was used for measurement.

[0341] The values ​​of the forward peak and the reverse peak are values ​​obtained by setting the peak in the program and calculating the height from the baseline. The measured oxidation potential or reduction potential is calibrated by the calibration material ferrocene to obtain the HOMO or LUMO value.

[0342] HOMO = 4.8 - (oxidation potential of ferrocene - oxidation potential of sample)

[0343] LUMO = 4.8 - (oxidation potential of ferrocene - reduction potential of sample)

[0344] The reversibility of the following Equation 1 was calculated by measuring the forward peak and the reverse peak of the following compound in the oxidation range or the reduction range and is shown in the following Table 1.

[0345] [Equation 1]

[0346] Reversibility = I r / I f

[0347] In equation 1, I r refers to the height of the reverse peak, I f It refers to the height of the positive peak.

[0348] In the following Tables 1 to 11, calculated LUMO or calculated HOMO is the absolute value of LUMO or HOMO calculated by time-dependent density functional theory (DFT) of Gaussian program. AC3LUMO or AC3HOMO is the HOMO or LUMO value measured by AC3.

[0349] The following compounds HTL1 to HTL5 were evaluated as hole transport materials (HT) and are shown in Table 1 below.

[0350]

[0351] The service life shown in the following Tables 1 to 11 refers to the service life (%) of the device, the device structure is as follows, and in each example, only the applied layer material is changed.

[0352] Positive electrode (ITO) / hole injection layer ( The weight ratio of compound HTL1 and P1 is 97:3) / hole transport layer ( Compound HTL1) / Electron blocking layer ( Compound HTL2) / Emitting layer( The weight ratio of compound BH and BD1 is 97:3) / hole blocking layer ( Compound xETL) / Electron Transport Layer( The weight ratio of compound ETL and LiQ is 50:50) / electron injection layer ( LiQ) / negative electrode( The weight ratio of magnesium to silver is 10:1) / covering layer ( Compound CPL)

[0353]

[0354] [Table 1]

[0355]

[0356] The following compounds EB1 to EB25 were evaluated as electron blocking materials (EB) and are shown in Table 2 below.

[0357]

[0358]

[0359] [Table 2]

[0360]

[0361] The service life of each device including both a hole transport material (HT) and an electron blocking material (EB) was measured and shown in the following Table 3. The "difference" in the following Table 3 refers to the value of (oxidation stability of hole transport material (HT) - oxidation stability of electron blocking material (EB)).

[0362] [Table 3]

[0363]

[0364]

[0365] The following compounds were evaluated as light-emitting dopant materials (BD) and are shown in the following Table 4. The compounds are blue light-emitting dopants, and the stability of (-) radicals is a factor affecting the service life.

[0366]

[0367]

[0368] [Table 4]

[0369]

[0370] The following compounds as blue light-emitting host materials (BH) were evaluated and shown in Table 5 below. The dipole moment (DM) (Debye) was calculated using the quantum chemical calculation program Gaussian 03 manufactured by US Gaussian Corporation, and the density functional theory (DFT) was used to obtain the calculated value of the triplet energy by time-dependent density functional theory (TD-DFT) for the structure optimized using B3LYP as functional and 6-31G* as basis function. Q1 in Table 5 below is the value of [1.34×(dipole moment)-0.293].

[0371]

[0372] [Table 5]

[0373]

[0374] The service life of each device including both a blue light-emitting dopant material (BD) and a blue light-emitting host material (BH) was measured and shown in the following Table 6. The "LUMO difference" in the following Table 6 refers to the value of (LUMO of the blue light-emitting host material (BH) - LUMO of the blue light-emitting dopant material (BD)). In the following Table 6, DM means dipole moment.

[0375] [Table 6]

[0376]

[0377]

[0378] The following compounds were evaluated as electron transport materials (ET) and are shown in Table 7 below.

[0379]

[0380] [Table 7]

[0381]

[0382] The following compounds HB1 to HB7 were evaluated as hole blocking materials (HB) and are shown in Table 8 below.

[0383]

[0384] [Table 8]

[0385]

[0386] The lifespan of each device including both an electron transport material (ET) and a hole blocking material (HB) was measured and shown in the following Table 9. The "LUMO difference" in the following Table 9 refers to the value of (LUMO of electron transport material (ET) - LUMO of hole blocking material (HB)).

[0387] [Table 9]

[0388]

[0389] The following compounds were evaluated as light-emitting host materials (EML) and are shown in Table 10 below. Q2 in Table 10 below is [0.955-0.1786×(reversibility value in oxidation range (I r / I f )] value.

[0390]

[0391] [Table 10]

[0392]

[0393] The lifespan of each device including both an emitting host material (EML) and an electron transport material (ET) was measured and shown in the following Table 11. The "LUMO difference" in the following Table 11 refers to the value of (LUMO of emitting host material (EML) - LUMO of electron transport material (ET)).

[0394] [Table 11]

[0395]

[0396] Through the examples, it can be seen that the organic light emitting device including the compound having CV characteristics according to the present invention has a long lifespan characteristic.

Claims

1. An organic light-emitting device, comprising: Positive electrode; Negative electrode; as well as An organic material layer is provided between the positive electrode and the negative electrode, The organic material layer comprises a hole transport material HT and an electron blocking material EB, The hole transport material HT has a HOMO absolute value of 4.30 eV to 4.60 eV, and a reversibility value I in the oxidation range at a scan rate of 100 mV / sec when measuring the cyclic voltage current. r / I f is 0.83 or higher, and When measuring the cyclic voltage current, the reversibility value I of the electron blocking material EB in the oxidation range at a scan rate of 100 mV / s is r / I f Greater than 0.5, The hole transport material HT and the electron blocking material EB are each independently a compound represented by the following formula 1 or 2: [Formula 1] [Formula 2] In equations 1 and 2, X1 and X2 are each hydrogen or deuterium, or are directly single-bonded to each other to form a ring, R11 to R14 are the same as or different from each other and are each independently hydrogen; deuterium; an alkyl group having 1 to 6 carbon atoms; or an aryl group having 6 to 30 carbon atoms, R21 and R22 are the same as or different from each other and are each independently hydrogen; deuterium; or optionally bonded to an adjacent group to form a benzene ring, L11 and L21 to L23 are the same as or different from each other and are each independently a single bond; or an arylene group having 6 to 30 carbon atoms, Ar11 and Ar12 are the same as or different from each other and are each independently an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, Ar21 and Ar22 are the same as or different from each other and are each independently an aryl group having 6 to 30 carbon atoms; a dibenzofuranyl group; or a dibenzothiophenyl group, r11, r13, r14, r21 and r22 are each an integer from 0 to 4, and r12 is an integer from 0 to 3, and When r11 to r14, r21 and r22 are 2 or more, the substituents in the brackets are the same as or different from each other.

2. The organic light emitting device according to claim 1, wherein: (HT I r / I f )-(EB I r / I f ) is 0.15 or less, The HT I r / I f is the reversibility value of the hole transport material HT in the oxidation range at a scan rate of 100 mV / s, and The EB I r / I f is the reversibility value of the electron blocking material EB in the oxidation range at a scan rate of 100 mV / s.

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