Organic light emitting diode and device comprising the same

Abstract

The present invention relates to an organic light-emitting diode, comprising an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron transport layer stacked together; and a display device or lighting device comprising the organic light-emitting diode.

Description

Technical Field

[0001] The present invention relates to an organic light-emitting diode and an apparatus including said organic light-emitting diode. Background Technology

[0002] Organic light-emitting diodes (OLEDs), as self-emissive devices, possess wide viewing angles, excellent contrast ratios, fast response times, high brightness, superior driving voltage characteristics, and excellent color reproduction. A typical OLED comprises an anode, a hole transport layer (HTL), an emissive layer (EML), an electron transport layer (ETL), and a cathode, sequentially stacked on a substrate. In this regard, the HTL, EML, and ETL are thin films formed from organic and / or organometallic compounds.

[0003] When a voltage is applied to the anode and cathode, holes injected from the anode electrode move to the EML via the HTL, and electrons injected from the cathode move to the EML via the ETL. Holes and electrons recombine in the EML to generate excitons. Light emission occurs when the excitons transition from the excited state to the ground state. The injection and flow of holes and electrons should be balanced to ensure excellent efficiency in OLEDs with this structure.

[0004] Organic electronic diodes (OLEDs) incorporating various electron transport materials are well known in the art. However, there remains a need to improve the performance of such devices, particularly multi-emitting-layer OLEDs, especially in terms of efficiency and voltage.

[0005] Therefore, the object of the present invention is to provide an organic light-emitting diode that overcomes the defects of the prior art, particularly a multi-emitting-layer top-emitting OLED with improved performance, improved efficiency and improved voltage. Summary of the Invention

[0006] The objective is achieved by an organic light-emitting diode (OLED), which includes a stacked layer of an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron transport layer; wherein...

[0007] -The first charge generation layer is disposed between the first light-emitting layer and the second light-emitting layer;

[0008] -The first electron transport layer is stacked between the first light-emitting layer and the second light-emitting layer;

[0009] - The first electron transport layer stack includes a first electron transport layer and a second electron transport layer;

[0010] -The first electron transport layer comprises a compound of formula (I).

[0011] (Ar 1 -A c) a -X b (I);

[0012] -a and b are independently 1 or 2;

[0013] -c can be 0 or 1 independently;

[0014] -Ar 1 Independently selected from C6 to C 60 Aryl or C2 to C 42 Mixed aromatics,

[0015] -of which each Ar 1 It can be substituted by one or two independent substituents selected from the following: C6 to C6. 12 Aryl, C3 to C 11 Heteroaryl, and C1 to C6 alkyl, D, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, halogen, CN or PY(R) 10 )2, wherein Y is selected from O, S or Se, preferably O, and R 10 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or perdeuterated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkoxy;

[0016] -Among them, Ar 1 Each C6 to C 12 Aryl substituents and Ar 1 Each C3 to C 11 The heteroaryl substituents can be replaced by C1 to C4 alkyl groups or halogens;

[0017] -A is selected independently from C6 to C 30 Aryl,

[0018] -Each A may be substituted by one or two substituents independently selected from the following: C6 to C6 12 Aryl and C1 to C6 alkyl, D, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, halogen, CN or PY(R)10 )2, wherein Y is selected from O, S or Se, preferably O, and R 10 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or perdeuterated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkoxy;

[0019] -where each C6 to C on A 12 The aryl substituents can be replaced by C1 to C4 alkyl groups or halogens;

[0020] -X is selected independently from C2 to C. 42 heteroaryl and C6 to C 60 Aryl,

[0021] - where each X can be substituted by one or two substituents independently selected from the following: C6 to C6 12 Aryl, C3 to C 11 Heteroaryl, and C1 to C6 alkyl, D, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, halogen, CN or PY(R) 10 )2, wherein Y is selected from O, S or Se, preferably O, and R 10 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or perdeuterated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkoxy;

[0022] -where each C6 to C on X 12 aryl substituents and each C3 to C on X 11 The heteroaryl substituents can be replaced by C1 to C4 alkyl groups or halogens;

[0023] - The molecular dipole moment of the compound of formula (I) is ≥0D and ≤4D;

[0024] - The second electron transport layer comprises a compound of formula (II).

[0025] (Ar 2 ) m -(Z k -G)n (II);

[0026] -m and n are independently 1 or 2;

[0027] -k can be 0, 1, or 2 independently;

[0028] -Ar 2 Independently selected from C2 to C 42 heteroaryl and C6 to C 60 Aryl,

[0029] -of which each Ar 2 It can be substituted by one or two independent substituents selected from the following: C6 to C6. 12 Aryl, C3 to C 11 Heteroaryl, and C1 to C6 alkyl, D, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, halogen, CN or PY(R) 10 )2, wherein Y is selected from O, S or Se, preferably O, and R 10 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or perdeuterated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkoxy;

[0030] -Among them, Ar 2 Each C6 to C 12 Aryl substituents and Ar 2 Each C3 to C 11 The heteroaryl substituents can be replaced by C1 to C4 alkyl groups or halogens;

[0031] -Z is selected independently from C6 to C 30 Aryl,

[0032] - where each Z can be substituted by one or two substituents independently selected from the following: C6 to C6 12 Aryl and C1 to C6 alkyl, D, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, halogen, CN or PY(R) 10)2, wherein Y is selected from O, S or Se, preferably O, and R 10 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or perdeuterated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkoxy;

[0033] -where each C6 to C on Z 12 The aryl substituents can be replaced by C1 to C4 alkyl groups or halogens;

[0034] - Choose G such that the dipole moment of the compound G-phenyl is ≥1D and ≤7D; and

[0035] - The first electron transport layer and the second electron transport layer do not contain electrical dopants.

[0036] The objective is also achieved by means of a device including the organic light-emitting diode of the present invention, wherein the device is a display device or a lighting device.

[0037] In the display device or lighting device, the light may be emitted through a transparent cathode.

[0038] In the display device or lighting device, the light may be emitted through a transparent anode.

[0039] First electron transport layer

[0040] The first electron transport layer comprises a compound of formula (I).

[0041] (Ar 1 -A c ) a -X b (I).

[0042] The first electron transport layer may be composed of a compound of formula (I). Alternatively, the first electron transport layer may be composed of a compound of formula (I) and a mixture of one or more other compounds, provided that none of the other compounds are electrodopersants. The first electron transport layer may contain more than one compound of formula (I). In particular, the first electron transport layer may be composed of a compound of formula (I) and a mixture of other compounds known in the art as electron transport matrix compounds. Exemplary other electron transport matrix compounds that may be included are disclosed below.

[0043] In the compound of formula (I), the group "A" is a linkage (if present, i.e., in the case of c>1) to the group Ar. 1The spacer group of X. If the compound of formula (I) contains more than one group (Ar) 1 -A c If the group can or may not independently contain spacer group A, then the group may contain spacer group A.

[0044] In the compounds of formula (I), a and b are independently 1 or 2. Alternatively, a and b can both be 1.

[0045] In the compounds of formula (I), c is independently 0 or 1.

[0046] Ar 1 Independently selected from C6 to C 60 Aryl or C2 to C 42 heteroaryl, or C6 to C 54 Aryl or C2 to C 39 heteroaryl, or C6 to C 48 Aryl or C2 to C 36 heteroaryl, or C6 to C 42 Aryl or C2 to C 36 heteroaryl, or C6 to C 36 Aryl or C2 to C 30 heteroaryl, or C6 to C 30 Aryl or C2 to C 24 Mixed aromatic compounds.

[0047] Ar 1 It can be C6 to C independently. 54 Aryl, optionally C6 to C 48 Aryl, optionally C6 to C 42 Aryl, optionally C6 to C 36 Aryl, optionally C6 to C 30 Aryl and optionally C6 to C 24 Aryl.

[0048] Ar 1 It can be C2 to C independently 42 heteroaryl, optionally C2 to C 40 heteroaryl, optionally C2 to C 36 heteroaryl, optionally C2 to C 30 heteroaryl and optionally C2 to C 24 Mixed aromatic compounds.

[0049] In one implementation, Ar 1 Unlike X.

[0050] Ar 1 It may contain two or more fused aromatic rings, preferably three or more fused aromatic rings.

[0051] Ar1 It may contain at least one sp 3 Hybridized carbon atoms.

[0052] Ar 1 It may contain at least one carbon-carbon sp that is not integrated into the aromatic ring structure. 2 Olefin bond.

[0053] In one implementation, Ar 1 Independently selected from unsubstituted C2 to C 42 Heteroaryl groups, where heteroatoms are bonded to Ar via single bonds 1 In the molecular structure.

[0054] Ar 1 It can be independently selected from phenyl, naphthyl, anthraceneyl, fluoranthyl, xanthonyl, spiro-xanthonyl, fluorenyl, spiro-fluorenyl, triphenylsilyl, tetraphenylsilyl, dibenzo-furanyl, bi-dibenzofuranyl, pyrimidinyl, pyrazinyl, aryl-alkenyl, or groups having formula (IIa).

[0055]

[0056] in

[0057] - The asterisk "*" indicates the binding position of the group of formula (IIa) with A; and

[0058] -R 1 To R 5 Independently selected from H, C6 to C 12 Aryl and C3 to C 10 Or C4 to C5 heteroaryl groups.

[0059] Ar 1 It can be independently selected from phenyl, anthracene, fluorenyl, or groups of formula (IIa).

[0060]

[0061] Where R 1 To R 5 It is independently selected from H and phenyl.

[0062] Ar 1 It can be a group of formula (IIa),

[0063]

[0064] And R 1 To R 5 At least two of them are not H.

[0065] In the groups of formula (IIa), R 1 To R5 At least two of the elements not equal to H can be adjacent to each other. 1 To R 5 At least one of the groups that is not H can be in the adjacent position of the * position. In this respect, if the two groups are bonded to adjacent carbon atoms of the benzene ring in formula (IIa), the two groups are in the adjacent position to each other.

[0066] Ar 1 It can be independently selected from one of the following groups,

[0067]

[0068] The asterisks "*" indicate the binding positions of the group and A.

[0069] In Ar 1 When substituted, each substituent may be independently selected from phenyl, naphthyl, biphenyl, pyridyl, methylpyridyl, dimethylpyridyl, dibenzofuranyl, dibenzothiophenyl, and benzothiophenyl.

[0070] A can be independently selected from C6 to C6, whether substituted or unsubstituted. 30 Aryl, or C6 to C 24 Aryl, or C6 to C 18 Aryl.

[0071] A can be independently selected from phenylene, naphthylene, biphenylene, and terphenylene, wherein the group can be substituted or unsubstituted.

[0072] A can be independently selected from one or a combination of the following groups.

[0073]

[0074] Among them, with Ar 1 The binding site of X can be freely chosen; preferably,

[0075]

[0076] When A is substituted, each substituent on A can be independently selected from phenyl and C1 to C4 alkyl groups.

[0077] X can be independently selected from C2 to C. 39 heteroaryl and C6 to C 54 Aryl, optionally C2 to C 36 heteroaryl and C6 to C 48 Aryl, optionally C3 to C 30 heteroaryl and C6 to C 42 Aryl, optionally C3 to C 27 heteroaryl and C6 to C36 Aryl, optionally C3 to C 24 heteroaryl and C6 to C 30 Aryl, and optionally C3 to C 21 heteroaryl and C6 to C 24 Aryl group, wherein the corresponding group may be substituted or unsubstituted.

[0078] X can be independently selected from C2 to C. 39 Contains N-heteroaryl, C2 to C 39 Contains O-heteroaryl and C6 to C 54 Aryl, optionally C2 to C 36 Contains N-heteroaryl, C2 to C 36 Contains O-heteroaryl and C6 to C 48 Aryl, optionally C3 to C 30 Contains N-heteroaryl, C3 to C 30 Contains O-heteroaryl and C6 to C 42 Aryl, optionally C3 to C 27 Contains N-heteroaryl, C3 to C 27 Contains O-heteroaryl and C6 to C 36 Aryl, optionally C3 to C 24 Contains N-heteroaryl, C3 to C 24 Contains O-heteroaryl and C6 to C 30 Aryl, and optionally C3 to C 21 Contains N-heteroaryl, C3 to C 21 Contains O-heteroaryl and C6 to C 24 Aryl.

[0079] X can be independently selected from C2 to C. 39 Contains N-heteroaryl and C6 to C 54 Aryl, optionally C2 to C 36 Contains N-heteroaryl and C6 to C 48 Aryl, optionally C3 to C 30 Contains N-heteroaryl and C6 to C 42 Aryl, optionally C3 to C 27 Contains N-heteroaryl and C6 to C 36 Aryl, optionally C3 to C 24 Contains N-heteroaryl and C6 to C 30 Aryl, and optionally C3 to C 21 Contains N-heteroaryl and C6 to C 24 Aryl. In this respect, the corresponding N-containing heteroaryl group may contain one or more N atoms as the only one or more heteroatoms.

[0080] X may be independently selected from triazinyl, 1,2-diazinyl, 1,3-diazinyl, 1,4-diazinyl, quinazolinyl, benzoquinazolinyl, benzimidazolyl, quinolinyl, benzoquinolinyl, benzoacridyl, dibenzoacridyl, fluoranthyl, anthraceneyl, naphthyl, biphenylideneyl, phenanthrolinel, and dinaphthofuranyl, wherein the groups may be substituted or unsubstituted.

[0081] X may be independently selected from triazinyl, 1,2-diazinyl, 1,3-diazinyl, 1,4-diazinyl, quinazolinyl, benzoquinazolinyl, benzoacridyl, dibenzoacridyl, fluoranthyl, anthraceneyl, naphthyl, biphenylideneyl, phenanthrolinel, and dinaphthofuranyl, wherein the groups may be substituted or unsubstituted.

[0082] X may be independently selected from triazinyl, 1,2-diazinyl, 1,3-diazinyl, 1,4-diazinyl, quinazolinyl, benzoquinazolinyl, benzoacridyl, dibenzoacridyl, and fluoranthyl, wherein the groups may be substituted or unsubstituted.

[0083] X can be independently selected from one of the following groups,

[0084]

[0085] The asterisks "*" indicate the binding positions of the group and A.

[0086] When X is substituted, each substituent on X can be independently selected from phenyl, naphthyl, and biphenyl.

[0087] When X is substituted, the corresponding substituted X group can be,

[0088]

[0089]

[0090] The asterisks "*" indicate the binding positions of the group and A.

[0091] The compound of formula (I) may not contain the P=O moiety. The compound of formula (I) may not contain P(=O)aryl 2. The compound of formula (I) may not contain P(=O)alkyl 2. The compound of formula (I) may not contain P(=O)Ph 2. The compound of formula (I) may not contain P(=O)(CH 3) 2. The compound of formula (I) may not contain R'P(=O)R”, where R' and R” are linked together to form a ring, i.e., it does not contain cyclophosphine oxide. The compound of formula (I) may not contain R'P(=O)R”, where R' and R” are linked together to form a 7-membered ring.

[0092] The compound of formula (I) may not contain two P=O moieties. The compound of formula (I) may not contain two P(=O)aryl 2-membered compounds. The compound of formula (I) may not contain two P(=O)alkyl 2-membered compounds. The compound of formula (I) may not contain two P(=O)Ph 2-membered compounds. The compound of formula (I) may not contain two P(=O)(CH3) 2-membered compounds. The compound of formula (I) may not contain CN.

[0093] One or more of the following formulas may be excluded from the scope of compounds of formula (I).

[0094]

[0095]

[0096] The compound of formula (I) may contain 6 to 14 aromatic or heteroaromatic rings, optionally 7 to 13 aromatic or heteroaromatic rings, optionally 7 to 12 aromatic or heteroaromatic rings, optionally 9 to 11 aromatic or heteroaromatic rings. In this respect, the aromatic ring or the corresponding heteroaromatic ring is a simple aromatic ring, such as a 6-membered aromatic ring like phenyl, a 6-membered heteroaromatic ring (an example of which will be pyridyl), a 5-membered heteroaromatic ring (an example of which will be pyrroleyl), etc. In fused (hetero)aromatic ring systems, each ring is considered to be a simple ring in this respect. For example, naphthalene contains two aromatic rings.

[0097] Calculated using the TURBOMOLE V6.5 package with hybrid functional B3LYP and Gaussian 6-31G* basis sets, the molecular dipole moment of the compound of formula (I) can be ≥0D and ≤4D; or ≥0D and ≤3.5D; or ≥0D and ≤3.0D; or ≥0D and ≤2.5D; or ≥0D and ≤2.0D. In this respect, the dipole moment of a molecule containing N atoms... It is given by the following formula:

[0098]

[0099]

[0100] Where q i and The partial charge and position of atom i in the molecule. The dipole moment is determined by a semi-empirical molecular orbital method. The geometry of the molecular structure is optimized in the gas phase using a hybrid functional B3LYP with a 6-31G* basis set, as implemented in the package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). If more than one conformation is feasible, the conformation with the lowest total energy is selected to determine the bond lengths of the molecule.

[0101] In one embodiment, using the TURBOMOLE V6.5 package with hybrid functional B3LYP and Gaussian 6-31G* basis sets, the LUMO level of the compound of formula (I) is in the range of -1.90 eV to -1.60 eV, preferably -1.87 eV to -1.65 eV, and preferably -1.85 eV to -1.65 eV at an absolute scale with the vacuum level at zero.

[0102] The compounds of formula (I) may be selected from compounds A-1 to A-29 in Table 1 below.

[0103] Table 1:

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110] In one embodiment, using the TURBOMOLE V6.5 package with hybrid functional B3LYP and Gaussian 6-31G* basis sets, the LUMO level of the compound of formula (I) is calculated in the range of -1.90 eV to -1.60 eV, preferably -1.85 eV to -1.65 eV, at an absolute scale with the vacuum level at zero.

[0111] The first electron transport layer may be disposed between the light-emitting layer and the second electron transport layer. The first electron transport layer may be disposed in direct contact with the light-emitting layer. Alternatively, the first electron transport layer may be disposed in a "contact-sandwich" configuration between the light-emitting layer and the second electron transport layer.

[0112] The first electron transport layer may have a thickness of <50 nm, optionally between 1 and 30 nm, optionally between 1 and 10 nm, or optionally between 1 and 5 nm.

[0113] Second electron transport layer

[0114] The second electron transport layer comprises a compound of formula (II).

[0115] (Ar 2 ) m -(Z k -G) n (II).

[0116] The second electron transport layer may be composed of a compound of formula (II). Alternatively, the second electron transport layer may be composed of a compound of formula (II) and a mixture of one or more other compounds, provided that none of the other compounds are electrodopersants. The first electron transport layer may contain more than one compound of formula (II). The second electron transport layer may be composed of a compound of formula (II) and a mixture of other compounds known in the art as electron transport matrix compounds. Exemplary other electron transport matrix compounds that may be included are disclosed below.

[0117] In the compound of formula (II), the group "Z" is the linker (if present, i.e., in the case of k>1) of the group Ar. 2 and the spacer group of G. If the compound of formula (II) contains more than one group (Z k If -G), then the group may or may not independently contain the spacer group Z.

[0118] In equation (II), m and n are independently 1 or 2. In equation (II), m and n can be 1.

[0119] In equation (II), k is independently 0, 1, or 2. In equation (II), k can be independently 1 or 2.

[0120] Ar 2 Can be independently selected from C2 to C 39 heteroaryl and C6 to C 54 Aryl, optionally C2 to C 36 heteroaryl and C6 to C 48 Aryl, optionally C3 to C 30 heteroaryl and C6 to C 42 Aryl, optionally C3 to C 27 heteroaryl and C6 to C 36 Aryl, optionally C3 to C 24 heteroaryl and C6 to C 30Aryl, and optionally C3 to C 21 heteroaryl and C6 to C 24 Aryl.

[0121] Ar 2 Can be independently selected from C2 to C 39 Contains N-heteroaryl and C6 to C 54 Aryl, optionally C2 to C 36 Contains N-heteroaryl and C6 to C 48 Aryl, optionally C3 to C 30 Contains N-heteroaryl and C6 to C 42 Aryl, optionally C3 to C 27 Contains N-heteroaryl and C6 to C 36 Aryl, optionally C3 to C 24 Contains N-heteroaryl and C6 to C 30 Aryl, and optionally C3 to C 21 Contains N-heteroaryl and C6 to C 24 Aryl. In this respect, the corresponding N-containing heteroaryl group may contain one or more N atoms as the only one or more heteroatoms.

[0122] Ar 2 It may contain at least two fused 5- or 6-membered rings.

[0123] Ar 2 It may be independently selected from pyridyl, triazinyl, 1,2-diazinyl, 1,3-diazinyl, 1,4-diazinyl, quinazolinyl, benzoquinazolinyl, benzimidazolyl, quinolinyl, benzoquinolinyl, benzoacridyl, dibenzoacridyl, fluoranthyl, anthraceneyl, naphthyl, biphenylideneyl, phenanthrolinel, and dinaphthofuranyl, wherein the groups may be substituted or unsubstituted.

[0124] Ar 2 It can be independently selected from dibenzo-acridyl, 1,3-diazinyl, 1,4-diazinyl, anthraceneyl, triazinyl, phenanthrolinel, biphenylideneyl, pyridyl, and dinaphthofuranyl.

[0125] Ar 2 It can be independently selected from one of the following groups,

[0126]

[0127] The asterisk "*" indicates the binding position of the group to Z.

[0128] In Ar 2 In the case of being replaced, Ar 2 Each substituent may be independently selected from: phenyl, naphthyl, optionally β-naphthyl, pyridyl, and biphenyl, and the groups may be substituted or unsubstituted, respectively.

[0129] In Ar 2 In the case of being replaced, Ar 2 Each substituent may be independently selected from phenyl, pyridyl, and biphenyl, optionally biphenyl.

[0130] Z can be independently selected from C6 to C6. 24 Aryl, or C6 to C 18 Aryl, or C6 to C 12 Aryl group, which may be substituted or unsubstituted.

[0131] Z can be selected from phenylene, naphthylene, phenylene-naphthylene, biphenylene, and terphenylene, wherein the groups can be substituted or unsubstituted.

[0132] Z can be independently selected from one of the following groups,

[0133]

[0134] Among them, with Ar 2 The binding position of G can be freely chosen.

[0135] When Z is substituted, each substituent on Z can be independently selected from phenyl and C1 to C4 alkyl groups.

[0136] G was chosen such that, calculated using the hybrid functional B3LYP and Gaussian 6-31G* basis set via the TURBOMOLE V6.5 package, the dipole moment of the G-phenyl is ≥1D and ≤7D. The dipole moment unit “Debye” is abbreviated as “D”. The inventors have found it advantageous if the compound of formula (II) contains a group having a specific polarity, i.e., a specific dipole moment within the range mentioned above or below. It has also been found that if the compound of formula (II) further contains another polar group (a second polar group), it is still advantageous for the compound of formula (II) to contain such a polar group (a first polar group), the second polar group being suitable to balance the dipole moment of the first polar group in a manner that results in a low total dipole moment for the compound of formula (II). For example, if the compound is a symmetrical molecule containing the same first and second polar groups, the dipole moment can be 0 Debye. Therefore, the compound of formula (II) cannot be characterized by its total dipole moment. Therefore, analogous compounds containing the polar group "G" and the nonpolar group "phenyl" are used instead. In this respect, the dipole moment of compounds containing N atoms... It is given by the following formula:

[0137]

[0138]

[0139] Where q i and This represents the partial charge and position of atom i in the molecule. The dipole moment is determined by a semi-empirical molecular orbital method. As implemented in the package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), the geometry of the molecular structure is optimized in the gas phase using the hybrid functional B3LYP with a 6-31G* basis set. If more than one conformation is feasible, the conformation with the lowest total energy is selected to determine the bond lengths of the molecule. In this respect, the entire part G encompasses all possible substituents.

[0140] G can be selected such that the dipole moment of the compound G-phenyl is >1D; optionally ≥2D; optionally ≥2.5D, optionally ≥2.5D, optionally ≥3D, and optionally ≥3.5D. G can also be selected such that the dipole moment of the compound G-phenyl is ≤7D, optionally ≤6.5D, optionally ≤6D, optionally ≤5.5D, and optionally ≤5D. If more than one conformational isomer of the compound G-phenyl is feasible, the average dipole moment of the conformational isomers of G-phenyl is selected to be within this range. Conformational isomerism is a form of stereoisomerism in which isomers can interconvert to each other solely by rotation around a formally single bond.

[0141] By selecting G such that the dipole moment of the compound G-phenyl is within the aforementioned range, electron injection from adjacent different charge generation layers (CGLs) is improved, the voltage of the OLED device is reduced, and the cd / A efficiency of the OLED device is increased.

[0142] Exemplary compounds “G-phenyl” are listed in Table 2 below, wherein the portion of the corresponding compound is described.

[0143]

[0144] Instruction “G- Phenyl The "phenyl" part in "".

[0145] Table 2:

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157] G can be selected from dialkylphosphine oxide, diarylphosphine oxide, alkylarylphosphine oxide, diheteroarylphosphine oxide, arylheteroarylphosphine oxide, cyclic diarylphosphine oxide, phosphine oxide, aryl-containing phosphine oxide, heteroaryl-containing phosphine oxide, cyclic arylheteroarylphosphine, cyclic heteroarylphosphine oxide, nitriles, benzonitrile, nicotinic nitrile, amides, ureas, and C2 to C3. 42 Heteroaryl; wherein G may include one or more substituents connected to the group, wherein the one or more substituents are selected from C6 to C6. 18 Aryl, C1 to C 10 Alkyl, C2 to C 14 Heteroaryl. In this respect, "cyclic" refers to the "P=O" of the phosphine oxide group, which, correspondingly, is part of a ring formed with the other part of the group.

[0158] G can be selected from 2-C1 to C. 10 -alkyloxyphosphine group, di-C6 to C 10 -Aryloxyphosphine group, C 10 -C 42 Dihexaryloxyphosphine, C7-C 42 aryl heteroaryl phosphine, C8-C 42 Phosphorus oxide, containing C8-C 42 Aryl phosphine oxides, C8-C 63 heteroaryl phosphine oxide, C 12 -C 63 Cyclic aryloxyphosphine, C7-C 42 Cyclic aryl heteroaryl phosphine group, containing C7-C 42 Circular heteroaryl phosphine oxides, and C2 to C 39 heteroaryl, optionally C2 to C 35 heteroaryl, optionally C2 to C 32 heteroaryl, optionally C2 to C 29 heteroaryl, optionally C2 to C 25Heteroaryl; G may include one or more substituents connected to the group, wherein the one or more substituents are selected from C6 to C6. 12 Aryl, C1 to C6 alkyl, C2 to C 11 Mixed aromatic compounds.

[0159] G can be selected from di-C1 to C4-alkylphosphine group, di-C6 to C4-alkyloxy ... 10 -Aryloxyphosphine group, C 10 Dihexaryloxyphosphine, C7-C 25 aryl heteroaryl phosphine, C8-C 42 Phosphorus oxide, containing C8-C 42 Aryl phosphine oxides, C8-C 24 heteroaryl phosphine oxide, C 12 -C 42 Cyclic aryloxyphosphine, C7-C 25 Cyclic aryl heteroaryl phosphine group, containing C7-C 25 Circular heteroaryl phosphine oxides and C2 to C 25 Heteroaryl groups; wherein each G may include one or more substituents connected to the group, wherein the one or more substituents are selected from C6 to C6. 10 Aryl, C1 to C4 alkyl, C2 to C5 heteroaryl.

[0160] G is selected from dialkylphosphine oxide, diarylphosphine oxide, alkylarylphosphine oxide, diheteroarylphosphine oxide, arylheteroarylphosphine oxide, cyclic diarylphosphine oxide, phosphine oxide, aryl-containing phosphine oxide, heteroaryl-containing phosphine oxide, cyclic arylheteroarylphosphine oxide, cycline, benzonitrile, nicotinic nitrile, amide group, urea group, and C2 to C3 groups. 17 Heteroaryl; wherein each G may include one or more substituents connected to the group, wherein the one or more substituents are selected from phenyl, methyl, ethyl and pyridyl.

[0161] G can be independently selected from dimethylphosphinyl, diphenylphosphinyl, nitriles, benzonitrile, nicotinic nitrile, dihydro-benzimidazolone, diphenyl-propane, N,N-dimethylacetamide, amide, urea, imidazolyl, phenylbenzimidazolyl, ethylbenzimidazolyl, phenylbenzimidazolyl, phenylbenzimidazolyl, phenylbenzimidazolyl, pyridyl, bipyridyl, methylpyridyl, dimethylpyridyl, pyridinyl, pyrimidinyl, pyrazinyl, triphenyl-pyrazinyl, benzoquinoline, phenanthroline, phenylphenanthroline, quinazolyl, benzo[] Azolyl, benzimidazole, pyridyl-imidazopyridyl;

[0162]

[0163]

[0164]

[0165]

[0166] The asterisk "*" indicates the position of the combination.

[0167] G can be independently selected from dimethylphosphinyl, diphenylphosphinyl, 2-phenyl-1H-benzo[d]imidazolyl, 2-ethyl-1H-benzo[d]imidazolyl, 2-phenylbenzo[h]quinolinyl, pyridyl, 2,2'-bipyridyl, 5-phenylbenzo[4,5]imidazo[1,2-a]quinolinyl, 9-phenyl-1,10-phenanthrolinel, 2-quinazolinyl, 4-quinazolinyl, 4-phenyl-2-quinazolinyl and (pyridin-2-yl)imidazo[1,5-a]pyridyl;

[0168]

[0169]

[0170]

[0171]

[0172]

[0173] The asterisk "*" indicates the position of the combination.

[0174] The compounds of formula (II) may be selected from compounds B-1 to B-25 in Table 3 below.

[0175] Table 3:

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182] In one embodiment, using the TURBOMOLE V6.5 package with hybrid functional B3LYP and Gaussian 6-31G* basis sets, the LUMO level of the compound of formula (II) is calculated in the range of -2.30 eV to -1.20 eV, preferably -2.10 eV to -1.28 eV, at an absolute scale with the vacuum level at zero.

[0183] In one embodiment, the compound of formula (II) contains a polar group "G".

[0184] The compound of formula (II) may not contain the P=O moiety. The compound of formula (II) may not contain P(=O)aryl 2. The compound of formula (II) may not contain P(=O)alkyl 2. The compound of formula (II) may not contain P(=O)Ph 2. The compound of formula (II) may not contain P(=O)(CH 3) 2. The compound of formula (II) may not contain R'P(=O)R”, where R' and R” are linked together to form a ring, i.e., it does not contain cyclophosphine oxide. The compound of formula (II) may not contain R'P(=O)R”, where R' and R” are linked together to form a 7-membered ring.

[0185] The compound of formula (II) may not contain two P=O moieties. The compound of formula (II) may not contain two P(=O)aryl 2-membered compounds. The compound of formula (II) may not contain two P(=O)alkyl 2-membered compounds. The compound of formula (II) may not contain two P(=O)Ph 2-membered compounds. The compound of formula (II) may not contain two P(=O)(CH3) 2-membered compounds. The compound of formula (II) may not contain CN.

[0186] One or more of the following formulas may be excluded from the scope of compounds of formula (II).

[0187]

[0188]

[0189] If the second electron transport layer comprises compounds of formula (II) and compound (III), then specified amounts of the following combinations of compounds may be excluded (refer to Tables 3 and 4):

[0190] B-23:C-3 30:70v:v;

[0191] C-3:B-10 30:70v:v;

[0192] B-23:C-5 30:70v:v;

[0193] B-10:C-5 30:70v:v;

[0194] B-23:C-6 30:70v:v;

[0195] B-10:C-6 30:70v:v.

[0196] The following organic light-emitting diodes (OLEDs) containing the following compounds (a) and (b) can be excluded:

[0197] a) A tandem OLED in which the electron transport layer is arranged adjacent to and in direct contact with an n-type doped charge generation layer made of compound E and metallic lithium in a weight ratio of E:Li of 98:2.

[0198]

[0199] The composition of the electron transport layer is selected from B-23:C-3, B-10:C-3, B-23:C-5, B-10:C-5, B-23:C-6, and B-10:C-6; and the weight ratio of the first component and the second component in each of these compositions is 30:70.

[0200] b) Top-emitting blue OLED with the following structure

[0201]

[0202] in

[0203] HT-3 is

[0204]

[0205] F2 is

[0206]

[0207] C-1 is

[0208]

[0209] D-1 is

[0210]

[0211] H09 is the main body of a commercial blue luminescent material, and BD200 is the main body of a commercial blue luminescent material; both are supplied by SFC of South Korea.

[0212] The second electron transport layer may further comprise compound (III), wherein compound (III) comprises 8 to 13 aromatic or heteroaromatic rings, optionally 8 to 11 aromatic or heteroaromatic rings, optionally 9 to 11 aromatic or heteroaromatic rings, and optionally 9 aromatic or heteroaromatic rings, wherein one or more of the aromatic or heteroaromatic rings may be substituted with C1 to C4 alkyl groups. In this respect, the aromatic or heteroaromatic rings are simple aromatic rings, such as 6-membered aromatic rings like phenyl, 6-membered heteroaromatic rings like pyridyl, 5-membered heteroaromatic rings like pyrrole, etc. In fused (hetero)aromatic ring systems, each ring is considered a simple ring in this respect. For example, naphthalene comprises two aromatic rings.

[0213] The compound (III) may contain at least one heteroaromatic ring, optionally 1 to 5 heteroaromatic rings, optionally 1 to 4 heteroaromatic rings, optionally 1 to 3 heteroaromatic rings, and optionally 1 or 2 heteroaromatic rings.

[0214] The aromatic or heteroaromatic ring of compound (III) may be a 6-membered ring.

[0215] The heteroaromatic ring of the compound (III) may be an N-containing heteroaromatic ring, optionally all heteroaromatic rings are N-containing heteroaromatic rings, optionally all heteroaromatic rings contain N as the only type of heteroatom.

[0216] The compound (III) may comprise at least one 6-membered heteroaromatic ring containing one to three N atoms in each heteroaromatic ring, optionally one to three 6-membered heteroaromatic rings each containing one to three N atoms in each heteroaromatic ring.

[0217] The at least one 6-membered heteroaromatic ring contained in compound (III) may be an azazine. The at least one 6-membered heteroaromatic ring contained in compound (III) may be a triazine, a diazine, or a pyrazine.

[0218] If compound (III) contains two or more heteroaromatic rings, the heteroaromatic rings may be separated from each other by at least one aromatic ring that does not contain heteroatoms.

[0219] In one embodiment, the heteroatom in the heteroaromatic ring of compound (III) is bonded to the molecular structure of compound (III) via at least one double bond.

[0220] The molecular dipole moment of compound (III) can be calculated using the hybrid functional B3LYP and Gaussian 6-31G* basis set with the TURBOMOLE V6.5 package. It can be ≥0D and ≤4D; or ≥0.1D and ≤3.9D; or ≥0.2D and ≤3.7D; or ≥0.3D and ≤3.5D.

[0221] By selecting compound (III) according to these embodiments, the mobility of the second electron transport layer is further improved, the voltage of the OLED device is reduced, and the cd / A efficiency of the OLED device is increased.

[0222] In one embodiment, compound (III) is not a compound of formula (II). The compound of formula (III) may be selected from compounds C-1 to C-6 in Table 4 below.

[0223] Table 4:

[0224]

[0225]

[0226] When the second electron transport layer contains both a compound of formula (II) and a compound of formula (III), the weight ratio of formula (II) to compound (III) can be 1:99 to 99:1, or 10:90 to 60:40, or 20:80 to 50:50, or 25:75 to 40:60, or about 30:70.

[0227] In one embodiment, using the TURBOMOLE V6.5 package with hybrid functional B3LYP and Gaussian 6-31G* basis sets, the LUMO level of the compound of formula (III) is calculated in the range of -2.00 eV to -1.70 eV, preferably -1.95 eV to -1.80 eV, at an absolute scale with the vacuum level at zero.

[0228] In one embodiment, the compound (III) comprises a nitrogen-containing six-membered ring.

[0229] In another embodiment, the compound (III) comprises two nitrogen-containing six-membered rings.

[0230] In one embodiment, the compound of formula (I) is not a compound of formula (II). In another embodiment, the compound of formula (II) is not compound (III). In yet another embodiment, the compound of formula (I) is not compound (III). In another embodiment of the invention, all three compounds, namely the compound of formula (I), the compound of formula (II), and compound (III), differ from each other in that they have different molecular structures.

[0231] The second electron transport layer may be disposed between the first electron transport layer and the electron injection layer. The second electron transport layer may be arranged to be in direct contact with the first electron transport layer.

[0232] The second electron transport layer can be arranged to be "contact-clamped" between the first electron transport layer and the electron injection layer.

[0233] The second electron transport layer may be disposed between the first electron transport layer and the charge generation layer. The second electron transport layer may be disposed in direct contact with the charge generation layer. The second electron transport layer may be disposed in direct contact with the n-type CGL.

[0234] The second electron transport layer can be arranged to be "contact-pinched" between the first electron transport layer and the n-type CGL.

[0235] The thickness of the second electron transport layer can be <100nm, optionally between 10 and 90nm, optionally between 10 and 60nm, or optionally between 10 and 50nm.

[0236] Other feasible characteristics of OLED

[0237] The organic light-emitting diode (OLED) according to the present invention includes at least two light-emitting layers, namely a first light-emitting layer and a second light-emitting layer. Furthermore, the OLED may include additional light-emitting layers (a third light-emitting layer, a fourth light-emitting layer, etc.). When the OLED includes more than two light-emitting layers, only one electron transport layer stack may be provided between the two light-emitting layers. Alternatively, more than one electron transport layer stack may be present. For example, when the OLED includes a first light-emitting layer, a second light-emitting layer, and a third light-emitting layer, the first electron transport layer stack may be disposed between the first light-emitting layer and the second light-emitting layer, and the second electron transport layer stack may be disposed between the second light-emitting layer and the third light-emitting layer.

[0238] When an organic light-emitting diode (OLED) includes more than two light-emitting layers, there may be more than one charge-generating layer. For example, when an OLED includes a first light-emitting layer, a second light-emitting layer, and a third light-emitting layer, the first charge-generating layer may be disposed between the first light-emitting layer and the second light-emitting layer, and the second charge-generating layer may be disposed between the second light-emitting layer and the third light-emitting layer.

[0239] For the purposes of this disclosure, a stacked layer is an arrangement of two or more distinct layers. Each layer of the stacked layer can be distinguished from one another by the chemical properties of the materials included in the respective layers, i.e., they can be made of different compounds. The electron transport stacked layer according to this disclosure comprises at least two distinct layers, each made of an electron transport material.

[0240] The compounds of formula (I) and the compounds of formula (II) may be different from each other. That is, the compounds of formula (I) and the compounds of formula (II) may differ from each other in at least one structural aspect, particularly by at least one atom and / or group.

[0241] The first and second electron transport layers are free of electrodops. In this respect, "free" means that the corresponding compound (electrodopant) is contained only in the corresponding layer, which cannot be avoided during the preparation of the corresponding layer through standard purification methods and commonly used techniques. In this respect, the electrodopant is particularly, but not limited to, n-type electrodops. The n-type electrodopant can be selected from metals, or alkali metals, metal salts or alkaline earth metal salts and / or rare earth metal salts, or organoalkali metal complexes, or alkali metal complexes, or LiF, LiCl, LiBr, LiI, LiQ, metal borates, or mixtures thereof. Specifically, the first and second electron transport layers may be free of n-type electrodops. The n-type electrodopant can be a metal salt comprising at least one metal cation and at least one anion. The metal cation of the metal salt can be selected from alkali metals, alkaline earth metals, and rare earth metals, or selected from Li, Na, K, Rb, Cs, Mg, Ca, Sr, and Ba; or selected from Li, Mg, Ca, and Sr. The anion of the metal salt can be selected from quinolinol anion, phosphonophenol oxide anion, and borate anion.

[0242] In this regard, n-type electro-doped agents are, in particular but not limited to, elemental metals, or positively charged metals selected from alkali metals, alkaline earth metals, rare earth metals, and transition metals; transition metals; metal salts, or alkali metal salts, alkaline earth metal salts, and / or rare earth metal salts, or metal complexes, or alkali metal complexes, alkaline earth metal complexes, transition metal complexes, and / or rare earth metal complexes. Examples of n-type doped metal salts can be LiF, LiCl, LiBr, LiI, metal borates, metal quinoline alcohols, or mixtures thereof. Other examples of n-type electro-doped agents are strong chemical reducing agents. A general characteristic of such "redox" n-type doped agents can be that the energy level of the highest occupied molecular orbital (HOMO) is equivalent to the energy level of the lowest unoccupied molecular orbital of the corresponding electron transport matrix, which is below approximately -3.0 eV in typical OLED transport materials. It should be understood that the term "below approximately -3.0 eV" refers to negative values ​​less than -3.0 eV, such as -2.8 eV, -2.5 eV, -2.3 eV, -2.1 eV, or values ​​negatively less than -2.0 eV.

[0243] n-type electro-dopersive agents can be organic compounds such as those disclosed in EP1837926A1, WO07107306A1 or WO07107356A1.

[0244] The electrodoped agent is essentially non-luminescent.

[0245] The first electron transport layer and the second electron transport layer can be in direct contact with each other.

[0246] The electron transport layer stack can be composed of a first electron transport layer and a second electron transport layer.

[0247] The second electron transport layer can be in direct contact with the electron injection layer.

[0248] The electron injection layer can be composed of multiple individual electron injection sublayers.

[0249] The electron injection layer may contain a metal, or an alkali metal, a metal salt or an alkaline earth metal salt and / or a rare earth metal salt, or an organic alkali metal complex, or an alkali metal complex, or LiF, LiCl, LiBr, LiI, LiQ, a metal borate, or a mixture thereof.

[0250] The electron injection layer may be composed of the following substances: metal, or alkali metal, metal salt or alkaline earth metal salt and / or rare earth metal salt, or organic alkali metal complex, or alkali metal complex, or LiF, LiCl, LiBr, LiI, LiQ, metal borate, or mixtures thereof.

[0251] The compound of formula (II) may not be included in the electron-injected layer. The compound of formula (I) may not be included in the electron-injected layer. Compound (III) may not be included in the electron-injected layer.

[0252] The compound of formula (I), the compound of formula (II), and the compound of formula (III) may be different from each other and / or may not be included in the electron-injected layer, respectively.

[0253] The first electron transport layer stack can be disposed between the first light-emitting layer and the first charge-generating layer. The second electron transport layer of the first electron transport layer stack can be in direct contact with the first charge-generating layer.

[0254] The first electron transport layer and the second electron transport layer can be in direct contact with each other.

[0255] The electron transport layer stack can be composed of a first electron transport layer and a second electron transport layer.

[0256] The charge generation layer may include a p-type sublayer and an n-type sublayer, and the second electron transport layer may be in direct contact with the n-type sublayer.

[0257] The first charge-generating layer may contain a metal, or an alkali metal, a metal salt or an alkaline earth metal salt and / or a rare earth metal salt, or an organic alkali metal complex, or an alkali metal complex, or LiF, LiCl, LiBr, LiI, LiQ, a metal borate, or a mixture thereof.

[0258] The charge-generating layer may contain metals, or alkali metals, metal salts, or alkaline earth metal salts and / or rare earth metal salts, or organic alkali metal complexes, or alkali metal complexes, or LiF, LiCl, LiBr, LiI, LiQ, metal borates, or mixtures thereof in its n-type sublayer.

[0259] The first charge-generating layer may be composed of a metal, or an alkali metal, a metal salt or an alkaline earth metal salt and / or a rare earth metal salt, or an organic alkali metal complex, or an alkali metal complex, or LiF, LiCl, LiBr, LiI, LiQ, a metal borate, or a mixture thereof.

[0260] The n-type sublayer of the first charge generation layer may be composed of a metal, or an alkali metal, a metal salt or an alkaline earth metal salt and / or a rare earth metal salt, or an organic alkali metal complex, or an alkali metal complex, or LiF, LiCl, LiBr, LiI, LiQ, a metal borate, or a mixture thereof.

[0261] The organic light-emitting diode may further include an electron injection layer and a second electron transport layer stack, wherein the second electron transport layer stack is in direct contact with the electron injection layer. The second electron transport layer stack may contain the same compounds (I), (II), and (III) as the first layer stack, i.e., as defined in this disclosure, wherein the respective compounds may be selected independently.

[0262] The compound of formula (II) may not be included in the first charge-generating layer. The compound of formula (I) may not be included in the first charge-generating layer. Compound (III) may not be included in the first charge-generating layer.

[0263] The compound of formula (I), the compound of formula (II), and the compound of formula (III) may be different from each other and / or may not be included in the first charge-generating layer.

[0264] In the case where an organic light-emitting device includes more than one electron transport layer stack (i.e., other electron transport layer stacks besides the first electron transport layer stack), all the above-described features of the first electron transport layer stack can be applied independently to each electron transport layer stack.

[0265] In the case where an organic light-emitting device includes more than one charge-generating layer (i.e., other charge-generating layers besides the first charge-generating layer), all the above-described features of the first charge-generating layer can be applied independently to each charge-generating layer.

[0266] Organic light-emitting diodes may also include a substrate, which may be transparent or opaque.

[0267] Exemplary Implementation

[0268] According to one embodiment, an organic light-emitting diode (OLED) is provided, comprising a stacked layer of an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron transport layer; wherein...

[0269] -The first charge generation layer is disposed between the first light-emitting layer and the second light-emitting layer;

[0270] -The first electron transport layer is stacked between the first light-emitting layer and the second light-emitting layer;

[0271] - The first electron transport layer stack includes a first electron transport layer and a second electron transport layer;

[0272] -The first electron transport layer comprises a compound of formula (I).

[0273] (Ar 1 -A c ) a -X b (I);

[0274] -a and b are independently 1 or 2;

[0275] -c can be 0 or 1 independently;

[0276] -Ar 1 Independently selected from C6 to C 30 Aryl or C2 to C 24 Mixed aromatics,

[0277] -of which each Ar 1 It can be substituted by one or two independent substituents selected from the following: C6 to C6. 12 Aryl, C3 to C 11 Heteroaryl, and C1 to C6 alkyl, D, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, halogen, CN or PY(R) 10)2, wherein Y is selected from O, S or Se, preferably O, and R 10 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or perdeuterated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkoxy;

[0278] -Among them, Ar 1 Each C6 to C 12 Aryl substituents and Ar 1 Each C3 to C 11 The heteroaryl substituents can be replaced by C1 to C4 alkyl groups or halogens;

[0279] -A is selected independently from C6 to C 18 Aryl,

[0280] -Each A may be substituted by one or two substituents independently selected from the following: C6 to C6 12 Aryl and C1 to C6 alkyl, D, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, halogen, CN or PY(R) 10 )2, wherein Y is selected from O, S or Se, preferably O, and R 10 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or perdeuterated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkoxy;

[0281] -where each C6 to C on A 12 The aryl substituents can be replaced by C1 to C4 alkyl groups or halogens;

[0282] -X is selected independently from C3 to C 21 heteroaryl and C6 to C 24 Aryl,

[0283] - where each X can be substituted by one or two substituents independently selected from the following: C6 to C6 12 Aryl, C3 to C 11Heteroaryl, and C1 to C6 alkyl, D, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, halogen, CN or PY(R) 10 )2, wherein Y is selected from O, S or Se, preferably O, and R 10 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or perdeuterated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkoxy;

[0284] -where each C6 to C on X 12 aryl substituents and each C3 to C on X 11 The heteroaryl substituents can be replaced by C1 to C4 alkyl groups or halogens;

[0285] - The molecular dipole moment of the compound of formula (I) is ≥0D and ≤3.5D;

[0286] - The second electron transport layer comprises a compound of formula (II).

[0287] (Ar 2 ) m -(Z k -G) n (II);

[0288] -m and n are independently 1 or 2;

[0289] -k can be 0, 1, or 2 independently;

[0290] -Ar 2 Independently selected from C3 to C 30 heteroaryl and C6 to C 42 Aryl,

[0291] -of which each Ar 2 It can be substituted by one or two independent substituents selected from the following: C6 to C6. 12 Aryl, C3 to C 11Heteroaryl, and C1 to C6 alkyl, D, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, halogen, CN or PY(R) 10 )2, wherein Y is selected from O, S or Se, preferably O, and R 10 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or perdeuterated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkoxy;

[0292] -Among them, Ar 2 Each C6 to C 12 Aryl substituents and Ar 2 Each C3 to C 11 The heteroaryl substituents can be replaced by C1 to C4 alkyl groups or halogens;

[0293] -Z is selected independently from C6 to C 18 Aryl,

[0294] - where each Z can be substituted by one or two substituents independently selected from the following: C6 to C6 12 Aryl and C1 to C6 alkyl, D, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, halogen, CN or PY(R) 10 )2, wherein Y is selected from O, S or Se, preferably O, and R 10 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or perdeuterated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkoxy;

[0295] -where each C6 to C on Z 12 The aryl substituents can be replaced by C1 to C4 alkyl groups or halogens;

[0296] - Choose G such that the dipole moment of the compound G-phenyl is ≥2D and ≤6D; and

[0297] - The first electron transport layer and the second electron transport layer do not contain electrical dopants.

[0298] According to one embodiment, an organic light-emitting diode (OLED) is provided, comprising a stacked layer of an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron transport layer; wherein...

[0299] -The first charge generation layer is disposed between the first light-emitting layer and the second light-emitting layer;

[0300] -The first electron transport layer is stacked between the first light-emitting layer and the second light-emitting layer;

[0301] - The first electron transport layer stack includes a first electron transport layer and a second electron transport layer;

[0302] -The first electron transport layer comprises a compound of formula (I).

[0303] (Ar 1 -A c ) a -X b (I);

[0304] -a and b are independently 1 or 2;

[0305] -c can be 0 or 1 independently;

[0306] -Ar 1 Independently selected from C6 to C 30 Aryl,

[0307] -of which each Ar 1 It can be substituted by one or two independent substituents selected from the following: phenyl, naphthyl, biphenyl, pyridyl, methylpyridyl, dimethylpyridyl, dibenzofuranyl, dibenzothiophenyl and benzothiophenyl;

[0308] -A is selected independently from C6 to C 18 Aryl,

[0309] -Each A may be substituted by one or two independent substituents selected from phenyl and C1 to C4 alkyl groups;

[0310] -X is selected independently from C3 to C 21 Contains N-heteroaryl, C3 to C 21 Contains O-heteroaryl and C6 to C 24 Aryl,

[0311] -Each X may be substituted by one or two independent substituents selected from phenyl, naphthyl and biphenyl;

[0312] - The molecular dipole moment of the compound of formula (I) is ≥0D and ≤3.0D;

[0313] - The second electron transport layer comprises a compound of formula (II).

[0314] (Ar 2 ) m -(Z k -G) n (II);

[0315] -m and n are independently 1 or 2;

[0316] -k can be 0, 1, or 2 independently;

[0317] -Ar 2 Independently selected from C3 to C 21 heteroaryl and C6 to C 24 Aryl,

[0318] -of which each Ar 2 It may be substituted by one or two independent substituents selected from the following: phenyl, pyridyl and biphenyl, optionally p-biphenyl;

[0319] -Z is selected independently from C6 to C 18 Aryl,

[0320] -Each Z may be substituted by one or two independent substituents selected from phenyl and C1 to C4 alkyl groups;

[0321] -G is selected from dialkylphosphine oxide, diarylphosphine oxide, alkylarylphosphine oxide, nitriles, benzonitrile, nicotinic nitrile, amides, ureas, and C2 to C3 groups. 42 Heteroaryl; wherein G may include one or more substituents connected to the group, wherein the one or more substituents are selected from C6 to C6. 18 Aryl, C1 to C 10 Alkyl, C2 to C 14 heteroaryl; and

[0322] - The first electron transport layer and the second electron transport layer do not contain electrical dopants.

[0323] According to one embodiment, an organic light-emitting diode (OLED) is provided, comprising a stacked layer of an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron transport layer; wherein...

[0324] -The first charge generation layer is disposed between the first light-emitting layer and the second light-emitting layer;

[0325] -The first electron transport layer is stacked between the first light-emitting layer and the second light-emitting layer;

[0326] - The first electron transport layer stack includes a first electron transport layer and a second electron transport layer;

[0327] -The first electron transport layer comprises a compound of formula (I).

[0328] (Ar 1 -A c ) a -X b (I);

[0329] -a and b are independently 1 or 2;

[0330] -c can be 0 or 1 independently;

[0331] -Ar 1 The group is independently selected from phenyl, naphthyl, anthraceneyl, fluoranthyl, xanthonyl, spiro-xanthonyl, fluorenyl, spiro-fluorenyl, triphenylsilyl, tetraphenylsilyl, or a group having formula (IIa).

[0332]

[0333] in

[0334] - The asterisk "*" indicates the binding position of the group of formula (IIa) with A; and

[0335] -R 1 To R 5 Independently selected from H, C6 to C 12 Aryl and C3 to C 10 Heteroaryl or C4 to C5 heteroaryl

[0336] -of which each Ar 1 It can be substituted by one or two independent substituents selected from the following: phenyl, naphthyl, biphenyl, pyridyl, methylpyridyl, dimethylpyridyl, dibenzofuranyl, dibenzothiophenyl and benzothiophenyl;

[0337] -A is independently selected from phenylene, naphthylene, biphenylene, and terphenylene.

[0338] -Each A may be substituted by one or two independent substituents selected from phenyl and C1 to C4 alkyl groups;

[0339] -X is selected independently from C3 to C 21 Contains N-heteroaryl and C6 to C 24 Aryl,

[0340] -Each X may be substituted by one or two independent substituents selected from phenyl, naphthyl and biphenyl;

[0341] - The molecular dipole moment of the compound of formula (I) is ≥0D and ≤2.5D;

[0342] - The second electron transport layer comprises a compound of formula (II).

[0343] (Ar 2 ) m -(Z k -G) n (II);

[0344] -m and n are independently 1 or 2;

[0345] -k is independently 1 or 2;

[0346] -Ar 2 Independently selected from C3 to C 21 Contains N-heteroaryl and C6 to C 24 Aryl,

[0347] -of which each Ar 2 It may be substituted by one or two independent substituents selected from the following: phenyl, pyridyl and biphenyl, optionally p-biphenyl;

[0348] -Z is independently selected from phenylene, naphthylene, phenylene-naphthylene, biphenylene, and terphenylene.

[0349] -Each Z may be substituted by one or two independent substituents selected from phenyl and C1 to C4 alkyl groups;

[0350] -G is selected from C2 to C 25 Heteroaryl; G may include one or more substituents connected to the group, wherein the one or more substituents are selected from C6 to C6. 12 Aryl, C1 to C6 alkyl, C2 to C 11 heteroaryl; and

[0351] - The first electron transport layer and the second electron transport layer do not contain electrical dopants.

[0352] According to one embodiment, an organic light-emitting diode (OLED) is provided, comprising a stacked layer of an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron transport layer; wherein...

[0353] -The first charge generation layer is disposed between the first light-emitting layer and the second light-emitting layer;

[0354] -The first electron transport layer is stacked between the first light-emitting layer and the second light-emitting layer;

[0355] - The first electron transport layer stack includes a first electron transport layer and a second electron transport layer;

[0356] -The first electron transport layer comprises a compound of formula (I).

[0357] (Ar 1 -A c ) a -X b (I);

[0358] -a and b are independently 1 or 2;

[0359] -c can be 0 or 1 independently;

[0360] -Ar 1 Independently selected from phenyl, anthracene, fluorenyl, or groups of formula (IIa),

[0361]

[0362] Where R 1 To R 5 Independently selected from H and phenyl,

[0363] -of which each Ar 1 It can be substituted by one or two independent substituents selected from the following: phenyl, naphthyl, biphenyl, pyridyl, methylpyridyl, dimethylpyridyl, dibenzofuranyl, dibenzothiophenyl and benzothiophenyl;

[0364] -A is independently selected from phenylene, naphthylene, biphenylene, and terphenylene.

[0365] -Each A may be substituted by one or two independent substituents selected from phenyl and C1 to C4 alkyl groups;

[0366] -X is independently selected from triazinyl, 1,2-diazinyl, 1,3-diazinyl, 1,4-diazinyl, quinazolinyl, benzoquinazolinyl, benzimidazolyl, quinolinyl, benzoquinolinyl, benzoacridyl, dibenzoacridyl, fluoranthyl, anthraceneyl, naphthyl, biterpenoidyl, phenanthrolinel, and dinaphthofuranyl.

[0367] -Each X may be substituted by one or two independent substituents selected from phenyl, naphthyl and biphenyl;

[0368] - The molecular dipole moment of the compound of formula (I) is ≥0D and ≤2.0D;

[0369] - The second electron transport layer comprises a compound of formula (II).

[0370] (Ar 2 ) m -(Z k -G) n (II);

[0371] -m and n are independently 1 or 2;

[0372] -k is independently 1 or 2;

[0373] -Ar 2 Independently selected from pyridyl, triazinyl, 1,2-diazinyl, 1,3-diazinyl, 1,4-diazinyl, quinazolinyl, benzoquinazolinyl, benzimidazolyl, quinolinyl, benzoquinolinyl, benzoacridyl, dibenzoacridyl, fluoranthyl, anthraceneyl, naphthyl, biterpenoidyl, phenanthrolinel, and dinaphthofuranyl.

[0374] -of which each Ar 2 It may be substituted by one or two independent substituents selected from the following: phenyl, pyridyl and biphenyl, optionally p-biphenyl;

[0375] -Z is independently selected from phenylene, naphthylene, phenylene-naphthylene, biphenylene, and terphenylene.

[0376] -Each Z may be substituted by one or two independent substituents selected from phenyl and C1 to C4 alkyl groups;

[0377] -G is selected from di-C1 to C4-alkylphosphine groups, di-C6 to C4-alkyloxyphosphine groups, and di-C6 to C4-alkyloxyphosphine groups. 10 -Aryloxyphosphine group and C2 to C 25 Heteroaryl groups; wherein the corresponding G may include one or more substituents connected to the group, wherein the one or more substituents are selected from C6 to C6. 10 aryl, C1 to C4 alkyl, C2 to C5 heteroaryl; and

[0378] - The first electron transport layer and the second electron transport layer do not contain electrical dopants.

[0379] According to one embodiment, an organic light-emitting diode (OLED) is provided, comprising a stacked layer of an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron transport layer; wherein...

[0380] -The first charge generation layer is disposed between the first light-emitting layer and the second light-emitting layer;

[0381] -The first electron transport layer is stacked between the first light-emitting layer and the second light-emitting layer;

[0382] - The first electron transport layer stack includes a first electron transport layer and a second electron transport layer;

[0383] -The first electron transport layer comprises a compound of formula (I).

[0384] (Ar 1-A c ) a -X b (I);

[0385] -a and b are independently 1 or 2;

[0386] -c can be 0 or 1 independently;

[0387] -Ar 1 It is a group of formula (IIa).

[0388]

[0389] And R 1 To R 5 At least two of them are not H;

[0390] -of which each Ar 1 It can be substituted by one or two independent substituents selected from the following: phenyl, naphthyl, biphenyl, pyridyl, methylpyridyl, dimethylpyridyl, dibenzofuranyl, dibenzothiophenyl and benzothiophenyl;

[0391] -A is independently selected from phenylene and biphenylene;

[0392] -Each A may be substituted by one or two independent substituents selected from phenyl and C1 to C4 alkyl groups;

[0393] -X is independently selected from triazinyl, 1,2-diazinyl, 1,3-diazinyl, 1,4-diazinyl, quinazolinyl, benzoquinazolinyl, benzoacridyl, dibenzoacridyl, fluoranthyl, anthraceneyl, naphthyl, biphenylideneyl, phenanthrolinel, and dinaphthofuranyl.

[0394] -Each X may be substituted by one or two independent substituents selected from phenyl, naphthyl and biphenyl;

[0395] - The molecular dipole moment of the compound of formula (I) is ≥0D and ≤2.0D;

[0396] - The second electron transport layer comprises a compound of formula (II).

[0397] (Ar 2 ) m -(Z k -G) n (II);

[0398] -m and n are independently 1 or 2;

[0399] -k is independently 1 or 2;

[0400] -Ar 2Independently selected from dibenzo-acridyl, 1,3-diazinyl, 1,4-diazinyl, anthraceneyl, triazinyl, phenanthrolinel, biterpenoidyl, pyridyl, and dinaphthofuranyl.

[0401] -of which each Ar 2 It may be substituted by one or two independent substituents selected from the following: phenyl, pyridyl and biphenyl, optionally p-biphenyl;

[0402] -Z is independently selected from phenylene, naphthylene, phenylene-naphthylene, biphenylene, and terphenylene.

[0403] -Each Z may be substituted by one or two independent substituents selected from phenyl and C1 to C4 alkyl groups;

[0404] -G is selected from dimethylphosphono, diphenylphosphono, nitriles, benzonitrile, nicotinic nitrile, dihydro-benzimidazolone, diphenyl-propane, N,N-dimethylacetamide, amide, urea, imidazolyl, phenylbenzimidazol, ethylbenzimidazol, phenylbenzoquinolinyl, phenylbenzimidazoloquinolinyl, pyridyl, bipyridyl, methylpyridyl, dimethylpyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triphenyl-pyrazinyl, benzoquinolinyl, phenanthrolinel, phenylphenanthrolinel, and pyridyl-imidazopyridyl; and

[0405] - The first electron transport layer and the second electron transport layer do not contain electrical dopants.

[0406] According to one embodiment, an organic light-emitting diode (OLED) is provided, comprising a stacked layer of an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron transport layer; wherein...

[0407] -The first charge generation layer is disposed between the first light-emitting layer and the second light-emitting layer;

[0408] -The first electron transport layer is stacked between the first light-emitting layer and the second light-emitting layer;

[0409] - The first electron transport layer stack includes a first electron transport layer and a second electron transport layer;

[0410] -The first electron transport layer comprises a compound of formula (I).

[0411] (Ar 1 -A c ) a -X b (I);

[0412] -a and b are independently 1 or 2;

[0413] -c can be 0 or 1 independently;

[0414] -Ar 1 It is a group of formula (IIa).

[0415]

[0416] And R 1 To R 5 At least two of them are not H, where R 1 To R 5 At least two of the elements not being H are adjacent to each other and / or R. 1 To R 5 At least one of the elements that is not H is located in the adjacent position of the * position;

[0417] -of which each Ar 1 It can be substituted by one or two independent substituents selected from the following: phenyl, naphthyl, biphenyl, pyridyl, methylpyridyl, dimethylpyridyl, dibenzofuranyl, dibenzothiophenyl and benzothiophenyl;

[0418] -A is independently selected from phenylene and biphenylene;

[0419] -Each A may be substituted by one or two independent substituents selected from phenyl and C1 to C4 alkyl groups;

[0420] -X is independently selected from triazinyl, 1,2-diazinyl, 1,3-diazinyl, 1,4-diazinyl, quinazolinyl, benzoquinazolinyl, benzoacridyl, dibenzoacridyl, and fluoranthyl.

[0421] -Each X may be substituted by one or two independent substituents selected from phenyl, naphthyl and biphenyl;

[0422] - The molecular dipole moment of the compound of formula (I) is ≥0D and ≤2.0D;

[0423] - The second electron transport layer comprises a compound of formula (II).

[0424] (Ar 2 ) m -(Z k -G) n (II);

[0425] -m and n are independently 1 or 2;

[0426] -k is independently 1 or 2;

[0427] -Ar 2 Independently selected from dibenzo-acridyl, 1,3-diazinyl, 1,4-diazinyl, anthraceneyl, triazinyl, phenanthrolinel, biterpenoidyl, pyridyl, and dinaphthofuranyl.

[0428] -of which each Ar 2 It may be substituted by one or two independent substituents selected from the following: phenyl, pyridyl and biphenyl, optionally p-biphenyl;

[0429] -Z is independently selected from phenylene, naphthylene, phenylene-naphthylene, biphenylene, and terphenylene.

[0430] -Each Z may be substituted by one or two independent substituents selected from phenyl and C1 to C4 alkyl groups;

[0431] -G is selected from dimethylphosphono, diphenylphosphono, 2-phenyl-1H-benzo[d]imidazolyl, 2-ethyl-1H-benzo[d]imidazolyl, 2-phenylbenzo[h]quinolinyl, pyridyl, 2,2'-bipyridyl, 5-phenylbenzo[4,5]imidazo[1,2-a]quinolinyl, 9-phenyl-1,10-phenanthrolinel, and (pyridin-2-yl)imidazo[1,5-a]pyridyl; and

[0432] - The first electron transport layer and the second electron transport layer do not contain electrical dopants.

[0433] According to one embodiment, an organic light-emitting diode (OLED) is provided, comprising a stacked layer of an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron transport layer; wherein...

[0434] -The first charge generation layer is disposed between the first light-emitting layer and the second light-emitting layer;

[0435] -The first electron transport layer is stacked between the first light-emitting layer and the second light-emitting layer;

[0436] - The first electron transport layer stack includes a first electron transport layer and a second electron transport layer;

[0437] - The first electron transport layer comprises compounds selected from compounds A-1 to A-8 shown in Table 1;

[0438] - The second electron transport layer comprises a compound selected from compounds B-1 to B-25 shown in Table 3; and

[0439] - The first electron transport layer and the second electron transport layer do not contain electrical dopants.

[0440] According to one embodiment, an organic light-emitting diode (OLED) is provided, comprising a stacked layer of an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron transport layer; wherein...

[0441] -The first charge generation layer is disposed between the first light-emitting layer and the second light-emitting layer;

[0442] -The first electron transport layer is stacked between the first light-emitting layer and the second light-emitting layer;

[0443] - The first electron transport layer stack includes a first electron transport layer and a second electron transport layer;

[0444] -The first electron transport layer comprises a compound of formula (I).

[0445] (Ar 1 -A c ) a -X b (I);

[0446] -a and b are independently 1 or 2;

[0447] -c can be 0 or 1 independently;

[0448] -Ar 1 Independently selected from C6 to C 30 Aryl or C2 to C 24 Mixed aromatics,

[0449] -of which each Ar 1 It can be substituted by one or two independent substituents selected from the following: C6 to C6. 12 Aryl, C3 to C 11 Heteroaryl, and C1 to C6 alkyl, D, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, halogen, CN or PY(R) 10 )2, wherein Y is selected from O, S or Se, preferably O, and R 10 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or perdeuterated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkoxy;

[0450] -Among them, Ar 1 Each C6 to C 12 Aryl substituents and Ar 1 Each C3 to C 11 The heteroaryl substituents can be replaced by C1 to C4 alkyl groups or halogens;

[0451] -A is selected independently from C6 to C 18 Aryl,

[0452] -Each A may be substituted by one or two substituents independently selected from the following: C6 to C6 12 Aryl and C1 to C6 alkyl, D, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, halogen, CN or PY(R) 10 )2, wherein Y is selected from O, S or Se, preferably O, and R 10 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or perdeuterated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkoxy;

[0453] -where each C6 to C on A 12 The aryl substituents can be replaced by C1 to C4 alkyl groups or halogens;

[0454] -X is selected independently from C3 to C 21 heteroaryl and C6 to C 24 Aryl,

[0455] - where each X can be substituted by one or two substituents independently selected from the following: C6 to C6 12 Aryl, C3 to C 11 Heteroaryl, and C1 to C6 alkyl, D, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, halogen, CN or PY(R) 10 )2, wherein Y is selected from O, S or Se, preferably O, and R 10 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or perdeuterated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkoxy;

[0456] -where each C6 to C on X 12 aryl substituents and each C3 to C on X11 The heteroaryl substituents can be replaced by C1 to C4 alkyl groups or halogens;

[0457] - The molecular dipole moment of the compound of formula (I) is ≥0D and ≤3.5D;

[0458] - The second electron transport layer comprises a compound of formula (II).

[0459] (Ar 2 ) m -(Z k -G) n (II);

[0460] -m and n are independently 1 or 2;

[0461] -k can be 0, 1, or 2 independently;

[0462] -Ar 2 Independently selected from C3 to C 30 heteroaryl and C6 to C 42 Aryl,

[0463] -of which each Ar 2 It can be substituted by one or two independent substituents selected from the following: C6 to C6. 12 Aryl, C3 to C 11 Heteroaryl, and C1 to C6 alkyl, D, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, halogen, CN or PY(R) 10 )2, wherein Y is selected from O, S or Se, preferably O, and R 10 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or perdeuterated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkoxy;

[0464] -Among them, Ar 2 Each C6 to C 12 Aryl substituents and Ar 2 Each C3 to C 11 The heteroaryl substituents can be replaced by C1 to C4 alkyl groups or halogens;

[0465] -Z is selected independently from C6 to C 18 Aryl,

[0466] - where each Z can be substituted by one or two substituents independently selected from the following: C6 to C6 12 Aryl and C1 to C6 alkyl, D, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, halogen, CN or PY(R) 10 )2, wherein Y is selected from O, S or Se, preferably O, and R 10 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or perdeuterated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkoxy;

[0467] -where each C6 to C on Z 12 The aryl substituents can be replaced by C1 to C4 alkyl groups or halogens;

[0468] - Choose G such that the dipole moment of the compound G-phenyl is ≥2D and ≤6D;

[0469] - The second electron transport layer may further comprise compound (III), wherein compound (III) comprises 8 to 13 aromatic or heteroaromatic rings; and

[0470] - The first electron transport layer and the second electron transport layer do not contain electrical dopants.

[0471] According to one embodiment, an organic light-emitting diode (OLED) is provided, comprising a stacked layer of an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron transport layer; wherein...

[0472] -The first charge generation layer is disposed between the first light-emitting layer and the second light-emitting layer;

[0473] -The first electron transport layer is stacked between the first light-emitting layer and the second light-emitting layer;

[0474] - The first electron transport layer stack includes a first electron transport layer and a second electron transport layer;

[0475] -The first electron transport layer comprises a compound of formula (I).

[0476] (Ar 1 -A c ) a -Xb (I);

[0477] -a and b are independently 1 or 2;

[0478] -c can be 0 or 1 independently;

[0479] -Ar 1 Independently selected from C6 to C 30 Aryl,

[0480] -of which each Ar 1 It can be substituted by one or two independent substituents selected from the following: phenyl, naphthyl, biphenyl, pyridyl, methylpyridyl, dimethylpyridyl, dibenzofuranyl, dibenzothiophenyl and benzothiophenyl;

[0481] -A is selected independently from C6 to C 18 Aryl,

[0482] -Each A may be substituted by one or two independent substituents selected from phenyl and C1 to C4 alkyl groups;

[0483] -X is selected independently from C3 to C 21 Contains N-heteroaryl, C3 to C 21 Contains O-heteroaryl and C6 to C 24 Aryl,

[0484] -Each X may be substituted by one or two independent substituents selected from phenyl, naphthyl and biphenyl;

[0485] - The molecular dipole moment of the compound of formula (I) is ≥0D and ≤3.0D;

[0486] - The second electron transport layer comprises a compound of formula (II).

[0487] (Ar 2 ) m -(Z k -G) n (II);

[0488] -m and n are independently 1 or 2;

[0489] -k can be 0, 1, or 2 independently;

[0490] -Ar 2 Independently selected from C3 to C 21 heteroaryl and C6 to C 24 Aryl,

[0491] -of which each Ar 2 It may be substituted by one or two independent substituents selected from the following: phenyl, pyridyl and biphenyl, optionally p-biphenyl;

[0492] -Z is selected independently from C6 to C 18 Aryl,

[0493] -Each Z may be substituted by one or two independent substituents selected from phenyl and C1 to C4 alkyl groups;

[0494] -G is selected from dialkylphosphine oxide, diarylphosphine oxide, alkylarylphosphine oxide, nitriles, benzonitrile, nicotinic nitrile, amides, ureas, and C2 to C3 groups. 42 Heteroaryl; wherein G may include one or more substituents connected to the group, wherein the one or more substituents are selected from C6 to C6. 18 Aryl, C1 to C 10 Alkyl, C2 to C 14 Mixed aromatics;

[0495] - The second electron transport layer may further comprise compound (III), wherein compound (III) comprises 8 to 13 aromatic or heteroaromatic rings;

[0496] - Compound (III) contains at least one heteroaromatic ring; and

[0497] - The first electron transport layer and the second electron transport layer do not contain electrical dopants.

[0498] According to one embodiment, an organic light-emitting diode (OLED) is provided, comprising a stacked layer of an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron transport layer; wherein...

[0499] -The first charge generation layer is disposed between the first light-emitting layer and the second light-emitting layer;

[0500] -The first electron transport layer is stacked between the first light-emitting layer and the second light-emitting layer;

[0501] - The first electron transport layer stack includes a first electron transport layer and a second electron transport layer;

[0502] -The first electron transport layer comprises a compound of formula (I).

[0503] (Ar 1 -A c ) a -X b (I);

[0504] -a and b are independently 1 or 2;

[0505] -c can be 0 or 1 independently;

[0506] -Ar 1The group is independently selected from phenyl, naphthyl, anthraceneyl, fluoranthyl, xanthonyl, spiro-xanthonyl, fluorenyl, spiro-fluorenyl, triphenylsilyl, tetraphenylsilyl, or a group having formula (IIa).

[0507]

[0508] in

[0509] - The asterisk "*" indicates the binding position of the group of formula (IIa) with A; and

[0510] -R 1 To R 5 Independently selected from H, C6 to C 12 Aryl and C3 to C 10 Or C4 to C5 heteroaryl groups

[0511] -of which each Ar 1 It can be substituted by one or two independent substituents selected from the following: phenyl, naphthyl, biphenyl, pyridyl, methylpyridyl, dimethylpyridyl, dibenzofuranyl, dibenzothiophenyl and benzothiophenyl;

[0512] -A is independently selected from phenylene, naphthylene, biphenylene, and terphenylene.

[0513] -Each A may be substituted by one or two independent substituents selected from phenyl and C1 to C4 alkyl groups;

[0514] -X is selected independently from C3 to C 21 Contains N-heteroaryl and C6 to C 24 Aryl,

[0515] -Each X may be substituted by one or two independent substituents selected from phenyl, naphthyl and biphenyl;

[0516] - The molecular dipole moment of the compound of formula (I) is ≥0D and ≤2.5D;

[0517] - The second electron transport layer comprises a compound of formula (II).

[0518] (Ar 2 ) m -(Z k -G) n (II);

[0519] -m and n are independently 1 or 2;

[0520] -k is independently 1 or 2;

[0521] -Ar 2 Independently selected from C3 to C 21Contains N-heteroaryl and C6 to C 24 Aryl,

[0522] -of which each Ar 2 It may be substituted by one or two independent substituents selected from the following: phenyl, pyridyl and biphenyl, optionally p-biphenyl;

[0523] -Z is independently selected from phenylene, naphthylene, phenylene-naphthylene, biphenylene, and terphenylene.

[0524] -Each Z may be substituted by one or two independent substituents selected from phenyl and C1 to C4 alkyl groups;

[0525] -G is selected from C2 to C 25 Heteroaryl; G may include one or more substituents connected to the group, wherein the one or more substituents are selected from C6 to C6. 12 Aryl, C1 to C6 alkyl, C2 to C 11 Mixed aromatics;

[0526] - The second electron transport layer may further comprise compound (III), wherein compound (III) comprises 8 to 13 aromatic or heteroaromatic rings;

[0527] - Compound (III) contains at least one heteroaromatic ring;

[0528] - The aromatic or heteroaromatic ring of compound (III) is a 6-membered ring; and

[0529] - The first electron transport layer and the second electron transport layer do not contain electrical dopants.

[0530] According to one embodiment, an organic light-emitting diode (OLED) is provided, comprising a stacked layer of an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron transport layer; wherein...

[0531] -The first charge generation layer is disposed between the first light-emitting layer and the second light-emitting layer;

[0532] -The first electron transport layer is stacked between the first light-emitting layer and the second light-emitting layer;

[0533] - The first electron transport layer stack includes a first electron transport layer and a second electron transport layer;

[0534] -The first electron transport layer comprises a compound of formula (I).

[0535] (Ar 1 -A c ) a -X b (I);

[0536] -a and b are independently 1 or 2;

[0537] -c can be 0 or 1 independently;

[0538] -Ar 1 Independently selected from phenyl, anthracene, fluorenyl, or groups of formula (IIa),

[0539]

[0540] Where R 1 To R 5 Independently selected from H and phenyl,

[0541] -of which each Ar 1 It can be substituted by one or two independent substituents selected from the following: phenyl, naphthyl, biphenyl, pyridyl, methylpyridyl, dimethylpyridyl, dibenzofuranyl, dibenzothiophenyl and benzothiophenyl;

[0542] -A is independently selected from phenylene, naphthylene, biphenylene, and terphenylene.

[0543] -Each A may be substituted by one or two independent substituents selected from phenyl and C1 to C4 alkyl groups;

[0544] -X is independently selected from triazinyl, 1,2-diazinyl, 1,3-diazinyl, 1,4-diazinyl, quinazolinyl, benzoquinazolinyl, benzimidazolyl, quinolinyl, benzoquinolinyl, benzoacridyl, dibenzoacridyl, fluoranthyl, anthraceneyl, naphthyl, biterpenoidyl, phenanthrolinel, and dinaphthofuranyl.

[0545] -Each X may be substituted by one or two independent substituents selected from phenyl, naphthyl and biphenyl;

[0546] - The molecular dipole moment of the compound of formula (I) is ≥0D and ≤2.0D;

[0547] - The second electron transport layer comprises a compound of formula (II).

[0548] (Ar 2 ) m -(Z k -G) n (II);

[0549] -m and n are independently 1 or 2;

[0550] -k is independently 1 or 2;

[0551] -Ar 2Independently selected from pyridyl, triazinyl, 1,2-diazinyl, 1,3-diazinyl, 1,4-diazinyl, quinazolinyl, benzoquinazolinyl, benzimidazolyl, quinolinyl, benzoquinolinyl, benzoacridyl, dibenzoacridyl, fluoranthyl, anthraceneyl, naphthyl, biterpenoidyl, phenanthrolinel, and dinaphthofuranyl.

[0552] -of which each Ar 2 It may be substituted by one or two independent substituents selected from the following: phenyl, pyridyl and biphenyl, optionally p-biphenyl;

[0553] -Z is independently selected from phenylene, naphthylene, phenylene-naphthylene, biphenylene, and terphenylene.

[0554] -Each Z may be substituted by one or two independent substituents selected from phenyl and C1 to C4 alkyl groups;

[0555] -G is selected from di-C1 to C4-alkylphosphine groups, di-C6 to C4-alkyloxyphosphine groups, and di-C6 to C4-alkyloxyphosphine groups. 10 -Aryloxyphosphine group and C2 to C 25 Heteroaryl groups; wherein the corresponding G may include one or more substituents connected to the group, wherein the one or more substituents are selected from C6 to C6. 10 Aryl, C1 to C4 alkyl, C2 to C5 heteroaryl;

[0556] - The second electron transport layer may further comprise compound (III), wherein compound (III) comprises 8 to 13 aromatic or heteroaromatic rings;

[0557] - Compound (III) contains at least one heteroaromatic ring;

[0558] -The aromatic or heteroaromatic ring of the compound (III) is a 6-membered ring;

[0559] - The heteroaromatic ring of compound (III) is an N-containing heteroaromatic ring; and

[0560] - The first electron transport layer and the second electron transport layer do not contain electrical dopants.

[0561] According to one embodiment, an organic light-emitting diode (OLED) is provided, comprising a stacked layer of an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron transport layer; wherein...

[0562] -The first charge generation layer is disposed between the first light-emitting layer and the second light-emitting layer;

[0563] -The first electron transport layer is stacked between the first light-emitting layer and the second light-emitting layer;

[0564] - The first electron transport layer stack includes a first electron transport layer and a second electron transport layer;

[0565] -The first electron transport layer comprises a compound of formula (I).

[0566] (Ar 1 -A c ) a -X b (I);

[0567] -a and b are independently 1 or 2;

[0568] -c can be 0 or 1 independently;

[0569] -Ar 1 It is a group of formula (IIa).

[0570]

[0571] And R 1 To R 5 At least two of them are not H;

[0572] -of which each Ar 1 It can be substituted by one or two independent substituents selected from the following: phenyl, naphthyl, biphenyl, pyridyl, methylpyridyl, dimethylpyridyl, dibenzofuranyl, dibenzothiophenyl and benzothiophenyl;

[0573] -A is independently selected from phenylene and biphenylene;

[0574] -Each A may be substituted by one or two independent substituents selected from phenyl and C1 to C4 alkyl groups;

[0575] -X is independently selected from triazinyl, 1,2-diazinyl, 1,3-diazinyl, 1,4-diazinyl, quinazolinyl, benzoquinazolinyl, benzoacridyl, dibenzoacridyl, fluoranthyl, anthraceneyl, naphthyl, biphenylideneyl, phenanthrolinel, and dinaphthofuranyl.

[0576] -Each X may be substituted by one or two independent substituents selected from phenyl, naphthyl and biphenyl;

[0577] - The molecular dipole moment of the compound of formula (I) is ≥0D and ≤2.0D;

[0578] - The second electron transport layer comprises a compound of formula (II).

[0579] (Ar 2 ) m -(Z k -G) n (II);

[0580] -m and n are independently 1 or 2;

[0581] -k is independently 1 or 2;

[0582] -Ar 2 Independently selected from dibenzo-acridyl, 1,3-diazinyl, 1,4-diazinyl, anthraceneyl, triazinyl, phenanthrolinel, biterpenoidyl, pyridyl, and dinaphthofuranyl.

[0583] -of which each Ar 2 It may be substituted by one or two independent substituents selected from the following: phenyl, pyridyl and biphenyl, optionally p-biphenyl;

[0584] -Z is independently selected from phenylene, naphthylene, phenylene-naphthylene, biphenylene, and terphenylene.

[0585] -Each Z may be substituted by one or two independent substituents selected from phenyl and C1 to C4 alkyl groups;

[0586] -G is selected from dimethylphosphono, diphenylphosphono, nitriles, benzonitrile, nicotinic nitrile, dihydro-benzimidazolone, diphenyl-propane, N,N-dimethylacetamide, amide, urea, imidazolyl, phenylbenzimidazol, ethylbenzimidazol, phenylbenzimidazolyl, phenylbenzimidazolyl, phenylbenzimidazolyl, pyridyl, bipyridyl, methylpyridyl, dimethylpyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triphenyl-pyrazinyl, benzoquinolinyl, phenanthrolinel, phenylphenanthrolinel, and pyridyl-imidazopyridyl.

[0587] - The second electron transport layer may further comprise compound (III), wherein compound (III) comprises 8 to 13 aromatic or heteroaromatic rings;

[0588] - Compound (III) contains at least one heteroaromatic ring;

[0589] -The aromatic or heteroaromatic ring of the compound (III) is a 6-membered ring;

[0590] - The heteroaromatic ring of compound (III) is an N-containing heteroaromatic ring;

[0591] - The compound (III) may comprise at least one six-membered heteroaromatic ring containing one to three N atoms in each heteroaromatic ring; and

[0592] - The first electron transport layer and the second electron transport layer do not contain electrical dopants.

[0593] According to one embodiment, an organic light-emitting diode (OLED) is provided, comprising a stacked layer of an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron transport layer; wherein...

[0594] -The first charge generation layer is disposed between the first light-emitting layer and the second light-emitting layer;

[0595] -The first electron transport layer is stacked between the first light-emitting layer and the second light-emitting layer;

[0596] - The first electron transport layer stack includes a first electron transport layer and a second electron transport layer;

[0597] -The first electron transport layer comprises a compound of formula (I).

[0598] (Ar 1 -A c ) a -X b (I);

[0599] -a and b are independently 1 or 2;

[0600] -c can be 0 or 1 independently;

[0601] -Ar 1 It is a group of formula (IIa).

[0602]

[0603] And R 1 To R 5 At least two of them are not H, where R 1 To R 5 At least two of the elements not being H are adjacent to each other and / or R. 1 To R 5 At least one of the elements that is not H is located in the adjacent position of the * position;

[0604] -of which each Ar 1 It can be substituted by one or two independent substituents selected from the following: phenyl, naphthyl, biphenyl, pyridyl, methylpyridyl, dimethylpyridyl, dibenzofuranyl, dibenzothiophenyl and benzothiophenyl;

[0605] -A is independently selected from phenylene and biphenylene;

[0606] -Each A may be substituted by one or two independent substituents selected from phenyl and C1 to C4 alkyl groups;

[0607] -X is independently selected from triazinyl, 1,2-diazinyl, 1,3-diazinyl, 1,4-diazinyl, quinazolinyl, benzoquinazolinyl, benzoacridyl, dibenzoacridyl, and fluoranthyl.

[0608] -Each X may be substituted by one or two independent substituents selected from phenyl, naphthyl and biphenyl;

[0609] - The molecular dipole moment of the compound of formula (I) is ≥0D and ≤2.0D;

[0610] - The second electron transport layer comprises a compound of formula (II).

[0611] (Ar 2 ) m -(Z k -G) n (II);

[0612] -m and n are independently 1 or 2;

[0613] -k is independently 1 or 2;

[0614] -Ar 2 Independently selected from dibenzo-acridyl, 1,3-diazinyl, 1,4-diazinyl, anthraceneyl, triazinyl, phenanthrolinel, biterpenoidyl, pyridyl, and dinaphthofuranyl.

[0615] -of which each Ar 2 It may be substituted by one or two independent substituents selected from the following: phenyl, pyridyl and biphenyl, optionally p-biphenyl;

[0616] -Z is independently selected from phenylene, naphthylene, phenylene-naphthylene, biphenylene, and terphenylene.

[0617] -Each Z may be substituted by one or two independent substituents selected from phenyl and C1 to C4 alkyl groups;

[0618] -G is selected from dimethylphosphono, diphenylphosphono, 2-phenyl-1H-benzo[d]imidazolyl, 2-ethyl-1H-benzo[d]imidazolyl, 2-phenylbenzo[h]quinolinyl, pyridyl, 2,2'-bipyridyl, 5-phenylbenzo[4,5]imidazo[1,2-a]quinolinyl, 9-phenyl-1,10-phenanthrolinel and (pyridin-2-yl)imidazo[1,5-a]pyridyl;

[0619] - The second electron transport layer may further comprise compound (III), wherein compound (III) comprises 8 to 13 aromatic or heteroaromatic rings;

[0620] - Compound (III) contains at least one heteroaromatic ring;

[0621] -The aromatic or heteroaromatic ring of the compound (III) is a 6-membered ring;

[0622] - The heteroaromatic ring of compound (III) is an N-containing heteroaromatic ring;

[0623] - The compound (III) may contain at least one 6-membered heteroaromatic ring having one to three N atoms in each heteroaromatic ring;

[0624] - The compound (III) comprises two or more heteroaromatic rings; and

[0625] - The first electron transport layer and the second electron transport layer do not contain electrical dopants.

[0626] According to one embodiment, an organic light-emitting diode (OLED) is provided, comprising a stacked layer of an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron transport layer; wherein...

[0627] -The first charge generation layer is disposed between the first light-emitting layer and the second light-emitting layer;

[0628] -The first electron transport layer is stacked between the first light-emitting layer and the second light-emitting layer;

[0629] -The first electron transport layer is stacked between the first light-emitting layer and the first charge-generating layer;

[0630] - The first electron transport layer stack includes a first electron transport layer and a second electron transport layer;

[0631] - The first electron transport layer comprises compounds selected from compounds A-1 to A-8 shown in Table 1;

[0632] - The second electron transport layer comprises compounds selected from compounds B-1 to B-25 shown in Table 3;

[0633] -And the second electron transport layer also comprises compounds selected from compounds C-1 to C-6 shown in Table 4; and

[0634] - The first electron transport layer and the second electron transport layer do not contain electrical dopants.

[0635] Other layers

[0636] According to the present invention, in addition to the layers already mentioned above, the organic electronic device may include other layers. Exemplary embodiments of the various layers are described below:

[0637] base

[0638] The substrate can be any substrate commonly used in the manufacture of electronic devices, such as organic light-emitting diodes (OLEDs). If light is to be emitted through the substrate, it should be a transparent or translucent material, such as a glass substrate or a transparent plastic substrate. If light is to be emitted through the top surface, the substrate can be a transparent or non-transparent material, such as a glass substrate, a plastic substrate, a metal substrate, or a silicon substrate.

[0639] Anode electrode

[0640] Either the first electrode or the second electrode included in the organic electronic device of the present invention can be an anode electrode. The anode electrode can be formed by deposition or sputtering of a material used to form the anode electrode. The material used to form the anode electrode can be a high work function material to facilitate hole injection. The anode material can also be selected from low work function materials (i.e., aluminum). The anode electrode can be a transparent or reflective electrode. Transparent conductive oxides, such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), aluminum zinc oxide (AlZO), and zinc oxide (ZnO), can be used to form the anode electrode. Metals, typically silver (Ag), gold (Au), or metal alloys, can also be used to form the anode electrode. A transparent or translucent anode can promote luminescence through the anode.

[0641] Hole injection layer

[0642] Hole injection layers (HILs) can be formed on the anode electrode using methods such as vacuum deposition, spin coating, printing, casting, slot die coating, and Langmuir-Blodgett (LB) deposition. When vacuum deposition is used to form the HIL, the deposition conditions can vary depending on the compound used to form the HIL and the desired structure and thermal properties of the HIL. However, generally, vacuum deposition conditions can include deposition temperatures from 100°C to 500°C and pressures of 10... -8 Up to 10 -3 Torr (1 Torr equals 133.322 Pa) and deposition rates of 0.1 to 10 nm / s.

[0643] When spin coating or printing is used to form the HIL, the coating conditions can vary depending on the compound used to form the HIL and the desired structure and thermal properties of the HIL. For example, coating conditions may include a coating speed of about 2000 rpm to about 5000 rpm and a heat treatment temperature of about 80°C to about 200°C. The solvent is removed by heat treatment after coating.

[0644] The HIL can be formed from any compound commonly used to form HIL. Examples of compounds that can be used to form HIL include: phthalocyanine compounds, such as copper phthalocyanine (CuPc), 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), TDATA, 2T-NATA, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethidedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), and polyaniline / poly(4-styrenesulfonate) (PANI / PSS).

[0645] The HIL may contain or be composed of p-type dopants, wherein the p-type dopants may be selected from, but are not limited to, tetrafluoro-tetracyanoquinone dimethyl ether (F4TCNQ), 2,2'-(perfluoronaphthalene-2,6-diylidene)-diammonium, 4,4',4”-((1E,1'E,1”E)-cyclopropane-1,2,3-trimethylenetris(cyanomethylmethylene))tris(2,3,5,6-tetrafluorobenzyl ether), or 2,2',2”-(cyclopropane-1,2,3-trimethylenetris(2-(p-cyanotetrafluorophenyl)acetonitrile). The HIL may be selected from hole transport matrix compounds doped with p-type dopants. Known doped hole transport... Typical examples of materials are: copper phthalocyanine (CuPc) with a HOMO level of approximately -5.2 eV; tetrafluoro-tetracyanoquinone dimethane (F4TCNQ) doped with a LUMO level of approximately -5.2 eV; zinc phthalocyanine (ZnPc) doped with F4TCNQ (HOMO = -5.2 eV); α-NPD (N,N'-bis(naphthyl-1-yl)-N,N'-bis(phenyl)-benzidine) doped with F4TCNQ; and α-NPD doped with 2,2'-(perfluoronaphthyl-2,6-diethylenediamine)dimalonitrile. The concentration of the p-type dopant can be selected from 1 wt% to 20 wt%, more preferably 3 wt% to 10 wt%.

[0646] The thickness of a hole-injection battery (HIL) can range from approximately 1 nm to approximately 100 nm, for example, from approximately 1 nm to approximately 25 nm. When the thickness of the HIL is within this range, the HIL can exhibit excellent hole injection characteristics without substantial loss of driving voltage.

[0647] Hole transport layer

[0648] Hole transport layers (HTLs) can be formed on hollow ink layers (HILs) via vacuum deposition, spin coating, slot die coating, printing, casting, Langmuir-Blodgett (LB) deposition, etc. When the HTL is formed by vacuum deposition or spin coating, the deposition and coating conditions can be similar to those for forming the HIL. However, the conditions for vacuum or solution deposition can vary depending on the compound used to form the HTL.

[0649] The HTL can be formed from any compound commonly used to form HTLs. Suitable compounds are disclosed, for example, in Yasuhiko Shirota and Hiroshi Kageyama, Chem. Rev. 2007, 107, 953-1010, and are incorporated herein by reference. Examples of compounds that can be used to form HTLs are: carbazole derivatives, such as N-phenylcarbazole or polyvinylcarbazole; benzidine derivatives, such as N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD), or N,N'-di(naphthyl-1-yl)-N,N'-diphenylbenzidine (α-NPD); and triphenylamine-based compounds, such as 4,4',4”-tris(N-carbazolyl)triphenylamine (TCTA). In these compounds, TCTA can transport holes and suppress exciton diffusion into the EML.

[0650] The thickness of the HTL can be in the range of about 5 nm to about 250 nm, preferably about 10 nm to about 200 nm, even more preferably about 20 nm to about 190 nm, even more preferably about 40 nm to about 180 nm, even more preferably about 60 nm to about 170 nm, even more preferably about 80 nm to about 160 nm, even more preferably about 100 nm to about 160 nm, and even more preferably about 120 nm to about 140 nm. A preferred thickness of the HTL can be from 170 nm to 200 nm.

[0651] When the thickness of the HTL is within this range, the HTL can have excellent hole transport characteristics without substantial loss of driving voltage.

[0652] Electron blocking layer

[0653] The function of the electron blocking layer (EBL) is to prevent electrons from transferring from the light-emitting layer to the hole transport layer, thereby confining electrons within the light-emitting layer. This improves efficiency, operating voltage, and / or lifetime. Typically, the electron blocking layer comprises a triarylamine compound. The LUMO level of the triarylamine compound can be closer to the vacuum level than the LUMO level of the hole transport layer. Compared to the HOMO level of the hole transport layer, the electron blocking layer can have a HOMO level further away from the vacuum level. The thickness of the electron blocking layer can be selected between 2 and 20 nm.

[0654] If the electron blocking layer has a high triplet energy level, it can also be called a triplet control layer.

[0655] If a phosphorescent green or blue emitting layer is used, the function of the triplet control layer is to reduce triplet quenching. Therefore, higher luminous efficiency from the phosphorescent emitting layer can be achieved. The triplet control layer is selected from triarylamine compounds whose triplet energy level is higher than that of the phosphorescent emitter in the adjacent emitting layer. Compounds suitable for the triplet control layer, particularly triarylamine compounds, are described in EP 2 722 908A1.

[0656] Emissive Layer (EML)

[0657] The EML can be formed on HTL by vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, etc. When the EML is formed using vacuum deposition or spin coating, the deposition and coating conditions can be similar to those for HTL formation. However, the deposition and coating conditions can vary depending on the compound used to form the EML.

[0658] The light-emitting layer may not contain compounds of formulas (I) and (II) and / or compound (III).

[0659] The light-emitting layer (EML) can be formed by a combination of a host and a light-emitting dopant. Examples of the host are Alq3,4,4'-N,N'-dicarbazole-biphenyl (CBP), poly(n-vinylcarbazole) (PVK), 9,10-bis(naphthyl-2-yl)anthracene (ADN), 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBI), 3-tert-butyl-9,10-bis-2-naphthylanthracene (TBADN), stilbeneylarylene (DSA), and bis(2-(2-hydroxyphenyl)benzothiazole)zinc (Zn(BTZ)2).

[0660] The luminescent dopant can be a phosphorescent or fluorescent luminescent material. Phosphorescent luminescent materials and luminescent materials that emit light via thermally activated delayed fluorescence (TADF) are preferred due to their higher efficiency. The luminescent material can be a small molecule or a polymer.

[0661] Examples of red-emitting dopants include PtOEP, Ir(piq)3, and Btp2lr(acac), but are not limited to these. These compounds are phosphorescent, but fluorescent red-emitting dopants can also be used.

[0662] Examples of phosphorescent green luminescent dopants are Ir(ppy)3 (ppy = phenylpyridine), Ir(ppy)2 (acac), and Ir(mpyp)3.

[0663] Examples of phosphorescent blue emitting electron dopants are F₂Irpic, (F₂ppy)₂Ir(tmd), and Ir(dfppz)₃, as well as terfluorene. Examples of fluorescent blue emitting electron dopants are 4,4'-bis(4-diphenylaminostyryl)biphenyl (DPAVBi) and 2,5,8,11-tetratert-butylperylene (TBPe).

[0664] Based on 100 parts by weight of the substrate, the amount of the luminescent dopant can range from about 0.01 to about 50 parts by weight. Alternatively, the luminescent layer can be composed of a luminescent polymer. The thickness of the EML can be from about 10 nm to about 100 nm, for example from about 20 nm to about 60 nm. When the thickness of the EML is within this range, the EML can exhibit excellent luminescence without substantial loss of driving voltage.

[0665] Hole blocking layer (HBL)

[0666] Hole blocking layers (HBLs) can be formed on the EML using methods such as vacuum deposition, spin coating, slot die coating, printing, casting, and LB deposition to prevent holes from diffusing into the ETL. When the EML contains phosphorescent dopants, the HBL can also have triplet exciton blocking functionality.

[0667] When forming the HBL using vacuum deposition or spin coating, the deposition and coating conditions can be similar to those used to form the HIL. However, the deposition and coating conditions can vary depending on the compound used to form the HBL. Generally, any compound used to form an HBL can be used. Examples of compounds used to form an HBL include... Diazole derivatives, triazole derivatives, and phenanthroline derivatives.

[0668] The thickness of the HBL can be in the range of about 5 nm to about 100 nm, for example, about 10 nm to about 30 nm. When the thickness of the HBL is within this range, the HBL can have excellent hole blocking performance without substantial loss of driving voltage.

[0669] Electron Transport Layer (ETL)

[0670] The OLED according to the present invention includes at least two electron transport layers (ETLs). At least two of the electron transport layers are a first electron transport layer and a second electron transport layer as defined herein. Furthermore, the OLED may include other ETLs, which may or may not be as defined above. If an additional ETL is not as defined above, its characteristics may be as follows.

[0671] According to various embodiments, the OLED may include an electron transport layer stack comprising at least one first electron transport layer (ETL-1) comprising a compound of formula (I) and at least one second electron transport layer (ETL-2) comprising a compound of formula (II).

[0672] By appropriately adjusting the energy levels of a specific ETL layer, electron injection and transport can be controlled, and holes can be effectively blocked. Therefore, the OLED can have a long lifetime, improved performance, and stability.

[0673] Electron Injection Layer (EIL)

[0674] An electron transport layer (EIL) can be formed on the second electron transport layer stack. The EIL can facilitate the optional injection of electrons from the cathode into the second electron transport layer stack. The EIL is preferably formed directly on the second electron transport layer of the second electron transport layer stack, preferably in direct contact with the second electron transport layer of the second electron transport layer stack. Examples of materials used to form or contain in the EIL include lithium 8-hydroxyquinoline (LiQ), LiF, NaCl, CsF, Li₂O, BaO, Ca, Ba, Yb, and Mg, known in the art. Although the deposition and coating conditions for forming the EIL are similar to those for forming the HIL, the deposition and coating conditions can vary depending on the material used to form the EIL. The EIL may comprise an organic matrix material doped with an n-type dopant. The matrix material can be selected from materials conventionally used as matrix materials for electron transport layers.

[0675] The EIL can be composed of multiple individual EIL sublayers. In the case where the EIL is composed of multiple individual EIL sublayers, the number of sublayers is preferably two. Each individual EIL sublayer can contain different materials used to form the EIL.

[0676] The thickness of the EIL can be in the range of about 0.1 nm to about 10 nm, for example, in the range of about 0.5 nm to about 9 nm. When the thickness of the EIL is within this range, the EIL can have satisfactory electron injection characteristics without substantial loss of driving voltage.

[0677] The electron transport stack of the present invention is not part of the electron injection layer.

[0678] cathode electrode

[0679] If an electron transport layer (EIL) is present, a cathode electrode is preferably formed on, or more preferably in direct contact with, the EIL. In the context of this invention, the cathode and the EIL can be considered as a functional component capable of injecting electrons into an electron transport layer stack. The cathode electrode can be formed of a metal, alloy, conductive compound, or a mixture thereof. The cathode electrode can have a low work function. For example, the cathode electrode can be formed of lithium (Li), magnesium (Mg), aluminum (Al), aluminum (Al)-lithium (Li), calcium (Ca), barium (Ba), ytterbium (Yb), magnesium (Mg)-indium (In), magnesium (Mg)-silver (Ag), etc. Alternatively, the cathode electrode can be formed of a transparent conductive oxide such as ITO or IZO.

[0680] The thickness of the cathode electrode can be in the range of about 5 nm to about 1000 nm, for example, in the range of about 10 nm to about 100 nm. When the thickness of the cathode electrode is in the range of about 5 nm to about 50 nm, the cathode electrode can be transparent or translucent even if it is formed of metal or metal alloy. The transparent or translucent cathode can promote light emission through the cathode.

[0681] It should be understood that the cathode electrode and the electron injection layer are not part of the second electron transport layer or any other part of the electron transport layer stack.

[0682] Charge generation layer

[0683] The charge generating layer (CGL), i.e., the first CGL and any other CGL included in the OLED of the present invention, may include p-type CGL and n-type CGL. An intermediate layer may be disposed between the p-type layer and the n-type layer.

[0684] Typically, the charge generation layer GCL is a pn junction connecting an n-type charge generation layer (electron generation layer, n-type CGL) and an a-type charge generation layer (hole generation layer, p-type CGL). Electrons are generated on the n-side of the pn junction and injected into the layer adjacent to the anode direction. Similarly, holes are generated on the p-side of the pn junction and injected into the layer adjacent to the cathode direction.

[0685] A charge-generating layer is used in a series OLED (e.g., the OLED of this disclosure), which includes two or more light-emitting layers between a cathode and an anode. In a series OLED including two light-emitting layers, an n-type charge-generating layer provides electrons to a first light-emitting layer disposed near the anode, while a hole-generating layer provides holes to a second light-emitting layer disposed between the first light-emitting layer and the cathode.

[0686] The matrix material suitable for the hole generation layer can be any material conventionally used as a matrix material for hole injection and / or hole transport. Furthermore, the p-type dopant used for the hole generation layer can be a conventional material. For example, the p-type dopant can be selected from tetrafluoro-7,7,8,8-tetracyanoquinone dimethylane (F4-TCNQ), derivatives of tetracyanoquinone dimethylane, axialene derivatives, iodine, FeCl3, FeF3, and SbCl5. Additionally, the host material can be selected from N,N'-di(naphthyl-1-yl)-N,N-diphenyl-benzidine (NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1-biphenyl-4,4'-diamine (TPD), and N,N',N'-tetranaphthyl-benzidine (TNB). The p-type charge generation layer can be composed of CNHAT.

[0687] The n-type charge generation layer can be a layer of pure n-type dopant, such as a positively charged metal, or it can be composed of an organic matrix material doped with said n-type dopant. In one embodiment, the n-type dopant can be an alkali metal, an alkali metal compound, an alkaline earth metal, an alkaline earth metal compound, a transition metal, a transition metal compound, or a rare earth metal. In another embodiment, the metal can be selected from Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, La, Ce, Sm, Eu, Tb, Dy, and Yb. More specifically, the n-type dopant can be selected from Cs, K, Rb, Mg, Na, Ca, Sr, Eu, and Yb. The matrix material suitable for the n-type charge generation layer can be a material conventionally used as a matrix material for electron injection or electron transport layers. The matrix material may be, for example, selected from N-containing heterocyclic compounds such as triazine compounds or phenanthroline compounds such as compound E or bipyridine or terpyridine compounds, hydroxyquinoline derivatives such as tris(8-hydroxyquinoline)aluminum, benzo[a]azole derivatives and siliconecyclopentane derivatives.

[0688] The hole-generating layer can be arranged to be in direct contact with the n-type charge-generating layer.

[0689] The electron transport stack of the present invention is not part of the charge generation layer.

[0690] Organic light-emitting diode (OLED)

[0691] According to various embodiments of the present invention, OLED layers can be provided disposed between the aforementioned layers, on a substrate, or on a top electrode.

[0692] According to one aspect of the present invention, an organic light-emitting diode is provided, comprising: a substrate, an anode, a first hole injection layer, a first hole transport layer, a first electron blocking layer, a first light-emitting layer, a first optional hole blocking layer, a stack of first electron transport layers, an n-type charge generating layer, a hole generating layer, a second hole transport layer, a second electron blocking layer, a second light-emitting layer, a second optional hole blocking layer, a stack of second electron transport layers, a second electron injection layer, and a cathode.

[0693] According to one aspect of the present invention, an organic light-emitting diode (OLED) is provided, comprising: a substrate, an anode, a hole injection layer, a first hole transport layer, a first electron blocking layer, a first light-emitting layer, a first electron transport layer stack including a first electron transport layer and a second electron transport layer, a first charge generation layer, a second hole transport layer, a second electron blocking layer, a second light-emitting layer, a second electron transport layer stack including a third electron transport layer (= the first electron transport layer of the second stack) and a fourth electron transport layer (= the second electron transport layer of the second stack), a second charge generation layer, a third hole transport layer, a third electron blocking layer, a third light-emitting layer, a third electron transport layer stack including a fifth electron transport layer (= the first electron transport layer of the third stack) and a sixth electron transport layer (= the second electron transport layer of the third stack), an electron injection layer, and a cathode.

[0694] According to one aspect, the OLED may include the following layer structure: a substrate disposed adjacent to an anode electrode, the anode electrode disposed adjacent to a first hole injection layer, the first hole injection layer disposed adjacent to a first hole transport layer, the first hole transport layer disposed adjacent to a first electron blocking layer, the first electron blocking layer disposed adjacent to a first light-emitting layer, the first light-emitting layer disposed adjacent to a first electron transport layer stack including a first electron transport layer and a second electron transport layer, the first electron transport layer stack disposed adjacent to an electron injection layer, and the electron injection layer disposed adjacent to a cathode electrode.

[0695] For example, according to Figure 1 The OLED can be formed by the following method, wherein on a substrate 110, an anode 120, a first hole injection layer 130, a first hole transport layer 140, a first electron blocking layer 145, a first light-emitting layer 150, a first electron transport layer stack 160, an n-type charge generation layer 185, a hole generation layer 135, a second hole transport layer 141, a second electron blocking layer 146, a second light-emitting layer 151, a second electron transport layer stack 165, a second electron injection layer 181, and a cathode 190 are subsequently formed in the order described.

[0696] For example, according to Figure 2The OLED can be formed by the following method, wherein on the anode 120, a hole injection layer 130, a first hole transport layer 140, a first electron blocking layer 145, a first light-emitting layer 150, a first electron transport layer stack 160 including a first electron transport layer 161 and a second electron transport layer 162, a first charge generation layer 184 including an n-type CGL sublayer 184a and a p-type CGL sublayer 184b, a second hole transport layer 141, a second electron blocking layer 146, a second light-emitting layer 151, and a third electron transport layer (= the first electron transport layer of the second stack) are subsequently formed in the following order. The second electron transport layer stack 165 includes an electron transport layer 166 and a fourth electron transport layer (= the second electron transport layer of the second stack) 167, a second charge generation layer 186 including an n-type CGL sublayer 186a and a p-type CGL sublayer 186b, a third hole transport layer 142, a third electron blocking layer 147, a third light emitting layer 152, a third electron transport layer stack 168 including a fifth electron transport layer (= the first electron transport layer of the third stack) 163 and a sixth electron transport layer (= the second electron transport layer of the third stack) 164, an electron injection layer 181, and a cathode 190.

[0697] According to another aspect of the present invention, a method for manufacturing an organic electronic device is provided, the method using:

[0698] - At least one sedimentation source, preferably two sedimentation sources and more preferably at least three sedimentation sources.

[0699] Applicable deposition methods include:

[0700] -Deposited via vacuum thermal evaporation;

[0701] - Deposition via solution processing, preferably the processing being selected from spin coating, printing, casting; and / or

[0702] - Slit-type die coating.

[0703] In the case where one or more of the second electron transport layers contain compounds of formula (III) and (II), the two compounds can be deposited from two separate deposition sources by co-deposition or as a premix for a single source.

[0704] According to various embodiments of the present invention, the method may further include forming a light-emitting layer on the anode electrode and forming at least one layer selected from the following between the anode electrode and the first electron transport layer: forming a hole injection layer, forming a hole transport layer, or forming an electron-hole blocking layer.

[0705] According to various embodiments of the present invention, the method may further include the step of forming an organic light-emitting diode (OLED), wherein

[0706] - Form the first anode electrode on the substrate.

[0707] - A light-emitting layer is formed on the first anode electrode.

[0708] - An electron transport layer stack is formed on the light-emitting layer, and a charge generation layer is formed on the electron transport layer stack.

[0709] -and finally form the cathode electrode.

[0710] Optionally, a hole injection layer and a hole transport layer are formed between the first anode electrode and the light-emitting layer in the aforementioned order.

[0711] - A charge generation layer is formed between the electron transport layer stack and the cathode electrode.

[0712] According to one embodiment, the OLED may have the following layer structure, wherein the layers have the following order:

[0713] An anode, hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, optional hole blocking layer, electron transport layer stack, n-type CGL, p-type CGL, hole transport layer, electron blocking layer, light-emitting layer, optional hole blocking layer, electron transport layer stack, n-type CGL, p-type CGL, hole transport layer, electron blocking layer, light-emitting layer, optional hole blocking layer, electron transport layer stack, electron injection layer, and cathode.

[0714] According to another aspect of the present invention, an electronic device is provided, comprising at least one organic light-emitting device according to any embodiment described throughout this application. Preferably, the electronic device comprises an organic light-emitting diode (OLED) of one of the embodiments described throughout this application. More preferably, the electronic device is a display device or a lighting device.

[0715] In one embodiment, the organic electronic device according to the invention may further include a layer comprising an axial ene compound and / or a quinone dimethane compound.

[0716] In one embodiment, the axial ene compound and / or the quinone dimethane compound may be substituted with one or more halogen atoms and / or with one or more electron-withdrawing groups. Electron-withdrawing groups may be selected from nitrile groups, haloalkyl groups, perhaloalkyl groups, or perfluorinated alkyl groups. Other examples of electron-withdrawing groups may be acyl groups, sulfonyl groups, or phosphoryl groups.

[0717] Alternatively, the acyl group, sulfonyl group, and / or phosphoryl group may comprise a halogenated and / or a perhalogenated hydrocarbon group. In one embodiment, the perhalogenated hydrocarbon group may be a perfluorinated hydrocarbon group. Examples of perfluorinated hydrocarbon groups may be perfluoromethyl, perfluoroethyl, perfluoropropyl, perfluoroisopropyl, perfluorobutyl, perfluorophenyl, and perfluorotolyl; examples of sulfonyl groups comprising halogenated hydrocarbon groups may be trifluoromethylsulfonyl, pentafluoroethylsulfonyl, pentafluorophenylsulfonyl, heptafluoropropylsulfonyl, nonafluorobutylsulfonyl, etc.

[0718] In one embodiment, the axialene and / or the quinone dimethane compound may be included in a hole injection, hole transport, and / or hole generation layer.

[0719] In one embodiment, the axial ene compound may have formula (XX) and / or the quinone dimethane compound may have formula (XXIa) or (XXIb):

[0720]

[0721] Where R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 11 R 12 R 15 R 16 R 20 R 21 Independently selected from the above electron-withdrawing groups and R 9 R 10 R 13 R 14 R 17 R 18 R 19 R 22 R 23 and R 24 It is independently selected from H, halogens and the above-mentioned electron-withdrawing groups.

[0722] In the following description, implementation methods will be illustrated with reference to embodiments. However, this disclosure is not limited to the following embodiments. Exemplary aspects will now be referred to in detail.

[0723] General definition

[0724] In this specification, unless otherwise defined, "alkyl group" may refer to an aliphatic hydrocarbon group. An alkyl group may refer to a "saturated alkyl group" without any double or triple bonds. As used herein, the term "alkyl" should encompass straight-chain as well as branched and cyclic alkyl groups. For example, C3-alkyl may be selected from n-propyl and isopropyl. Similarly, C4-alkyl encompasses n-butyl, sec-butyl, and tert-butyl. Likewise, C6-alkyl encompasses n-hexyl and cyclohexyl.

[0725] Unless otherwise explicitly stated, as indicated by the asterisk "*" used in this article, it represents the location where the corresponding marked part is bonded to another part.

[0726] C n The subscript number n in the formula is related to the total number of carbon atoms in the corresponding alkyl, aryl, heteroaryl, or aryl group.

[0727] As used herein, the terms “aryl” or “arylene” should encompass phenyl (C6-aryl), fused aromatic hydrocarbons such as naphthalene, anthracene, phenanthrene, and tetraphenyl. It also encompasses biphenyl and oligomeric or polyphenyl groups, such as terphenyl, phenyl-substituted biphenyl, phenyl-substituted terphenyl (e.g., tetraphenylphenyl group), etc. “Arylene” or “heteroarylene” refers to a group that connects two additional parts. In this specification, the terms “aryl group” or “arylene group” can refer to a group containing at least one aromatic hydrocarbon moiety, and all elements of the aromatic hydrocarbon moiety can have conjugated p orbitals, such as phenyl groups, naphthyl groups, anthraceneyl groups, phenanthryl groups, pyrene groups, fluorene groups, etc. It also encompasses spirocyclic compounds in which two aromatic moieties are connected to each other via spiro atoms, such as 9,9'-spirobis[9H-fluorene]yl. Aryl or arylene groups can include monocyclic or fused-ring polycyclic (i.e., connections sharing adjacent carbon atom pairs) functional groups.

[0728] As used herein, the term "heteroaryl" refers to an aryl group in which at least one carbon atom is substituted by a heteroatom. The term "heteroaryl" can refer to an aromatic heterocycle having at least one heteroatom, and all elements of the heteroaromatic hydrocarbon moiety can have conjugated p orbitals. The heteroatom can be selected from N, O, S, B, Si, P, Se, preferably N, O, and S. The heteroaryl ring may contain at least 1 to 3 heteroatoms. Preferably, the heteroaryl ring may contain at least 1 to 3 heteroatoms individually selected from N, S, and / or O. As in the case of "aryl" / "heteroaryl", the term "heteroaryl" includes, for example, spirocyclic compounds in which two aromatic moieties are linked to each other, such as spiro[fluorene-9,9'-xanthine]. Other exemplary heteroaryl groups are diazine, triazine, dibenzofuran, dibenzothiofuran, acridine, benzoacridine, dibenzoacridine, etc.

[0729] As used in this article, the term "alkenyl" refers to a group containing a carbon-carbon double bond -CR 1=CR 2 R 3 .

[0730] As used in this article, “fully halogenated” refers to a hydrocarbon group in which all hydrogen atoms of the hydrocarbon group are replaced by halogen (F, Cl, Br, I) atoms.

[0731] As used herein, the term "alkoxy" refers to a structural segment of the formula -OR, where R is a hydrocarbon group, preferably an alkyl or cycloalkyl group.

[0732] As used herein, the term "thioalkyl" refers to a structural segment of formula -SR, where R is a hydrocarbon group, preferably an alkyl or cycloalkyl group.

[0733] C n - The subscript 'n' in heteroaryl refers only to the number of carbon atoms, excluding the number of heteroatoms. In this paper, it is clear that C3 heteroaryl groups are aromatic compounds containing three carbon atoms, such as pyrazoles, imidazoles, etc. Zyrazole, thiazole, etc.

[0734] As used herein, the term "heteroaryl" should encompass pyridine, quinoline, benzoquinoline, quinazoline, benzoquinazoline, pyrimidine, pyrazine, triazine, benzimidazole, benzothiazole, benzo[4,5]thieno[3,2-d]pyrimidine, carbazole, xanthanil, phenanthanil Azides, benzo[acridine], dibenzo[acridine], etc.

[0735] In this specification, the term single bond refers to a direct bond.

[0736] As used herein, the term "fluorinated" refers to a hydrocarbon group in which at least one hydrogen atom is replaced by a fluorine atom. A fluorinated group in which all hydrogen atoms are replaced by fluorine atoms is called a perfluorinated group and is specifically indicated by the term "fluorinated".

[0737] For the purposes of this invention, if one of the hydrogen atoms contained in a group is replaced by another group, then the group is "replaced" by another group, wherein the other group is a substituent.

[0738] For the purposes of this invention, the expression "between" regarding a layer between two other layers does not exclude the presence of an additional layer disposed between one of the two other layers. For the purposes of this invention, the expression "directly in contact" regarding two layers in direct contact with each other means that no other layer is disposed between the two layers. A layer deposited on top of another layer is considered to be in direct contact with that layer.

[0739] The term "contact sandwich" refers to a three-layer arrangement in which the middle layer is in direct contact with the two adjacent layers.

[0740] Regarding the electron transport layer stack of the present invention, the compound mentioned in the experimental section is the most preferred.

[0741] Lighting devices can be any device used for illumination, irradiation, signal transmission, or projection. They are correspondingly classified as lighting, irradiation, signal transmission, and projection devices. A lighting device typically consists of a light radiation source, a device that transmits the radiant flux into space in the desired direction, and a housing that connects the components into a single device and protects the radiation source and light transmission system from damage and the influence of the surrounding environment.

[0742] According to another aspect, the organic electroluminescent device according to the invention comprises two, three, or more light-emitting layers. OLEDs comprising more than one light-emitting layer are also described as tandem OLEDs or stacked OLEDs.

[0743] The organic light-emitting device (OLED) can be a bottom-emitting or top-emitting device. The organic light-emitting device (OLED) can emit light through a transparent anode or through a transparent cathode.

[0744] On the other hand, it relates to a device that includes at least one organic light-emitting device (OLED).

[0745] Devices that include organic light-emitting diodes include, for example, displays or lighting panels.

[0746] In this invention, unless otherwise defined in the claims or elsewhere in this specification, the terms defined below shall apply.

[0747] In the context of this specification, the terms “different” or “different from” in relation to matrix materials refer to matrix materials with different structural formulas.

[0748] The terms "OLED" and "organic light-emitting diode" are used together and have the same meaning. As used herein, the term "organic electroluminescent device" can include both organic light-emitting diodes and organic light-emitting transistors (OLETs).

[0749] As used herein, “weight percentage,” “weight %,” “percentage by weight,” “weight %,” and variations thereof refer to the value obtained by dividing the weight of the composition, component, substance, or reagent as the corresponding electron transport layer by the total weight of the corresponding electron transport layer and multiplying by 100. It should be understood that the total weight percentage of all components, substances, and reagents in the corresponding electron transport layer and electron injection layer is selected so as not to exceed 100% by weight.

[0750] As used herein, “volume percentage,” “volume %,” “percentage by volume,” “volume %,” and variations thereof refer to the value obtained by dividing the volume of the composition, component, substance, or reagent that serves as the corresponding electron transport layer by the total volume of the corresponding electron transport layer and multiplying by 100. It should be understood that the total volume percentage of all components, substances, and reagents in the cathode layer is selected such that it does not exceed 100% by volume.

[0751] Whether explicitly stated or not, this document assumes that all numerical values ​​are modified by the term "about". As used herein, the term "about" refers to possible variations in quantity. Whether or not modified by the term "about", the claims include equivalents of the quantity.

[0752] It should be noted that, as used in this specification and the appended claims, the singular forms “a,” “an,” and “the” include a plurality of indicators, unless otherwise expressly stated.

[0753] The terms "does not contain," "does not contain," and "does not include" do not exclude impurities. Impurities have no technical effect on the objective of this invention.

[0754] In the context of this specification, the terms "substantially non-luminescent" or "non-luminescent" mean that the contribution of the compound or layer to the visible emission spectrum from the device is less than 10%, preferably less than 5%, relative to the visible emission spectrum. The visible emission spectrum is an emission spectrum with wavelengths from about ≥380 nm to about ≤780 nm.

[0755] Preferably, the organic semiconductor layer comprising the compound of formula (I) is substantially non-luminescent or non-luminescent.

[0756] Operating voltage (also known as U) is 10 mA / cm². 2 Measurements are taken in volts (V).

[0757] The candela / ampere efficiency (also known as the cd / A efficiency) is at 10 mA / cm². 2 The following measurements are in units of candela / ampere.

[0758] External quantum efficiency (also known as EQE) is measured as a percentage (%).

[0759] Color spaces are described by coordinates CIE-x and CIE-y (International Commission on Illumination 1931). CIE-y is particularly important for blue light emission. A smaller CIE-y value indicates a deeper blue. Efficiency values ​​are compared at the same CIE-y value.

[0760] The highest occupied molecular orbital (also known as HOMO) and the lowest unoccupied molecular orbital (also known as LUMO) are measured in electron volts (eV).

[0761] The terms “OLED,” “organic light-emitting diode,” “organic light-emitting device,” “organic optoelectronic device,” and “organic light-emitting diode” are used together and have the same meaning.

[0762] The terms “lifespan” and “service life” are used together and have the same meaning.

[0763] Anodes and cathodes can be described as anodic electrode / cathode, or anodic / cathode, or anodic electrode layer / cathode electrode layer.

[0764] The room temperature (also known as the ambient temperature) is 23°C. Attached Figure Description

[0765] These and / or other aspects and advantages of the invention will become apparent and more readily understood from the following description of exemplary embodiments, taken in conjunction with the accompanying drawings, in which:

[0766] Figure 1 This is a schematic cross-sectional view of a multi-emitting-layer organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention;

[0767] Figure 2 This is a schematic cross-sectional view of a multi-emitting-layer OLED according to an exemplary embodiment of the present invention. Detailed Implementation

[0768] Exemplary embodiments of the present invention will now be described in detail with reference to the accompanying drawings, in which the same reference numerals refer to the same elements throughout. Exemplary embodiments are described below with reference to the accompanying drawings in order to explain aspects of the invention.

[0769] In this document, when a first element is referred to as being formed or arranged "on" or "above" a second element, the first element may be arranged directly on the second element, or it may be arranged with one or more other elements disposed therebetween. When a first element is referred to as being arranged "directly on" or "directly above" a second element, no other elements are disposed therebetween.

[0770] Figure 1This is a schematic cross-sectional view of an organic light-emitting diode (OLED) 200 according to an exemplary embodiment of the present invention. The OLED 200 includes a substrate 110, an anode 120, a first hole injection layer (HIL-1) 130, a first hole transport layer (HTL-1) 140, a first electron blocking layer (EBL-1) 145, a first light-emitting layer (EML-1) 150, a first electron transport layer (ETL-1) stack 160 including a first electron transport layer 161 and a second electron transport layer 162, an n-type charge generation layer (n-type CGL) 185, and a hole generation layer. (p-type charge generation layer; p-type GCL) 135, second hole transport layer (HTL-2) 141, second electron blocking layer (EBL-2) 146, second light emitting layer (EML-2) 151, second electron transport layer (ETL-2) stack 165 including third electron transport layer (= first electron transport layer of the second stack) 166 and fourth electron transport layer (= second electron transport layer of the second stack) 167, electron injection layer (EIL) 181 and cathode 190.

[0771] See Figure 2 OLED 200 includes an anode 120, a hole injection layer (HIL) 130, a first hole transport layer (HTL-1) 140, a first electron blocking layer (EBL-1) 145, a first light-emitting layer (EML-1) 150, a first electron transport layer (ETL-1) stack 160 including a first electron transport layer 161 and a second electron transport layer 162, a first charge generation layer (CGL-1) 184, a second hole transport layer (HTL-2) 141, a second electron blocking layer (EBL-2) 146, a second light-emitting layer (EML-2) 151, and a third electron transport layer (= the second stack of the first electron transport layer). The stack of the second electron transport layer (ETL-2) 165 including the fourth electron transport layer (= the second electron transport layer of the second stack) 167, the second charge generation layer (CGL-2) 186, the third hole transport layer (HTL-3) 142, the third electron blocking layer (EBL-3) 147, the third light emitting layer (EML-3) 152, the third electron transport layer (ETL-3) stack 168 including the fifth electron transport layer (= the first electron transport layer of the third stack) 163 and the sixth electron transport layer (= the second electron transport layer of the third stack) 164, the electron injection layer (EIL) 181, and the cathode 190. Figure 2 The OLED shown has a first light-emitting part A, a second light-emitting part B, and a third light-emitting part C.

[0772] Although Figure 1 and Figure 2 Although not shown, a sealing layer can also be formed on the cathode electrode 190 to seal the OLED 200. Furthermore, various other modifications can be applied to it.

[0773] In the following description, one or more exemplary embodiments of the present invention will be described in detail with reference to the following examples. However, these examples are not intended to limit the purpose and scope of the one or more exemplary embodiments of the present invention.

[0774] Detailed description

[0775] dipole moment

[0776] The dipole moment of a molecule containing N atoms It is given by the following formula:

[0777]

[0778]

[0779] Where q i and It represents the partial charge and position of atom i in the molecule.

[0780] The dipole moment is determined by a semi-empirical molecular orbital method.

[0781] As implemented in the package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), the geometry of the molecular structure is optimized in the gas phase using hybrid functionals B3LYP and 6-31G* basis sets. If more than one conformation is feasible, the conformation with the lowest total energy is selected to determine the bond lengths of the molecule.

[0782] Calculated HOMO and LUMO

[0783] HOMO and LUMO were calculated using the package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). The optimized geometry and HOMO and LUMO energy levels of the molecular structure were determined by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase. If more than one conformation was feasible, the conformation with the lowest total energy was selected.

[0784] OLED performance measurement

[0785] To evaluate the performance of the OLED device, current efficiency was measured at 20°C. The current-voltage characteristics were determined using a Keithley 2635 source measurement unit by applying a voltage (in V) and measuring the current flowing through the device under test (in mA). The voltage applied to the device varied between 0V and 10V in 0.1V increments. Similarly, the luminous density (in cd / m²) for each voltage value was measured using an InstrumentSystems CAS-140CT array spectrometer (calibrated by Deutsche Akkreditierungsstelle (DAkkS)). 2 To determine the luminous density-voltage characteristics and CIE coordinates (in units of 10 mA / cm²), the following parameters were used: 2 The cd / A efficiency was determined by interpolating the luminous density-voltage and current-voltage characteristics, respectively.

[0786] If applicable, the device lifetime LT can be achieved under environmental conditions (20°C) and 30 mA / cm. 2 The measurements were taken using a Keithley 2400 source meter and recorded in hours.

[0787] The brightness of the device is measured using a calibrated photodiode. Lifetime LT is defined as the time before the device's brightness decreases to 97% of its initial value.

[0788] The increase in operating voltage ΔU is used as a measure of the device's operating voltage stability. This increase is determined during the LT measurement by subtracting the operating voltage at the start of device operation from the operating voltage after 50 hours.

[0789] ΔU=[U(50h)-U(0h)]

[0790] The smaller the ΔU value, the better the stability of the operating voltage.

[0791] General procedures for OLED manufacturing

[0792] For top-emitting OLED devices, a substrate measuring 150mm × 150mm × 0.7mm was ultrasonically cleaned for 7 minutes with a 2% aqueous solution of Deconex FPD211, then rinsed with pure water for 5 minutes, and dried in a rotary rinse-dryer for 15 minutes. Subsequently, it was subjected to 10 -5 Up to 10 -7 Ag was deposited as an anode under millibar pressure.

[0793] Then, HT-1 and D-1 are vacuum co-deposited on the anode to form the HIL. Then, HT-1 is vacuum deposited on the HIL to form the HTL. Then, HT-2 is vacuum deposited on the HTL to form the electron blocking layer (EBL).

[0794] Subsequently, the first luminescent layer was formed on the EBL by co-deposition of HOST-1 and EMITTER-1.

[0795] Then, the compound of formula (I) is vacuum deposited onto the light-emitting layer to form a first electron transport layer. A second electron transport layer is then formed on the first electron transport layer by depositing a compound of formula (II), for example, OLED-1 to OLED-4. For a comparative example of an OLED, the second electron transport layer is formed on the first electron transport layer by depositing compound C-3.

[0796] For embodiments OLED-5 to OLED-15, a second electron transport layer is formed on the first electron transport layer by depositing a premix of compound (II) and compound (III).

[0797] Then, an n-type CGL is formed on the second electron transport layer by co-depositing compound E and lithium.

[0798] Then, HT-1 and D-1 were vacuum co-deposited on n-type CGL to form p-type CGL.

[0799] Then, HT-1 was vacuum deposited on p-type CGL to form HTL. Then, HT-2 was vacuum deposited on HTL to form EBL.

[0800] A second luminescent layer was then formed on the EBL by co-deposition of HOST-1 and EMITTER-1.

[0801] Then, the compound of formula (I) is vacuum deposited onto the light-emitting layer to form a first electron transport layer. A second electron transport layer is then formed on the first electron transport layer by depositing a compound of formula (II), for example, OLED-1 to OLED-4. For a comparative example of an OLED, the second electron transport layer is formed on the first electron transport layer by depositing compound C-3.

[0802] For embodiments OLED-5 to OLED-15, a second electron transport layer is formed on the first electron transport layer by depositing a premix of compound (II) and compound (III).

[0803] Then, n-CGL is formed on the second electron transport layer by co-deposition of compound E and lithium.

[0804] Then, HT-1 and D-1 are vacuum co-deposited on the n-type CGL to form the p-type CGL.

[0805] Then, HT-1 was vacuum deposited on HIL to form HTL. Then, HT-2 was vacuum deposited on HTL to form electron blocking layer (EBL).

[0806] Subsequently, a third luminescent layer was formed on the EBL by co-deposition of HOST-1 and EMITTER-1.

[0807] Then, the compound of formula (I) is vacuum deposited onto the light-emitting layer to form a first electron transport layer. A second electron transport layer is then formed on the first electron transport layer by depositing a compound of formula (II), for example, OLED-1 to OLED-4. For a comparative example of an OLED, the second electron transport layer is formed on the first electron transport layer by depositing compound C-3.

[0808] For embodiments OLED-5 to OLED-15, a second electron transport layer is formed on the first electron transport layer by depositing a premix of compound (II) and compound (III).

[0809] Then, a bilayer electron injection layer is formed on the electron transport layer by first depositing LiQ and then depositing Yb.

[0810] Then in 10 -7 0.01 to millibars The rate at which Ag:Mg evaporates to form a cathode.

[0811] An HT-3 capping layer is formed on the cathode.

[0812] The following details the stacked layers in a top-emitting OLED device. Layers are separated by forward slashes " / ". Layer thicknesses are given in square brackets [...], and mixing ratios are given in wt% in parentheses (...).

[0813] Table 6 details the stack-up layers used in the OLED device embodiments:

[0814] Ag[100nm] / HT-1:D-1(wt% 92:8)[10nm] / HT-1[24nm] / HT-2[5nm] / H09:BD200(wt% 97:3)[20nm] / Compound of Formula (I)[5nm] / Compound of Formula (II) or C-3[25nm] / E:Li(wt% 99:1)[15nm] / HT-1:D-1(wt% 90:10)[10nm] / HT-1[36nm] / HT-2[5nm] / H09:BD200(wt% 97:3)[20nm] / Formula ( Compound of formula (I) [5nm] / Compound of formula (II) or C-3 [25nm] / E:Li (wt% 99:1) [15nm] / HT-1:D-1 (wt% 90:10) [10nm] / HT-1 [57nm] / HT-2 [5nm] / H09:BD200 (wt% 97:3) [20nm] / Compound of formula (I) [5nm] / Compound of formula (II) or C-3 [30nm] / LiQ [1nm] / Yb [2nm] / Ag:Mg (wt% 90:10) [13nm] / HT-3 [65nm].

[0815] Table 7 details the stack-up layers used in the OLED device embodiments:

[0816] Ag[100nm] / HT-1:D-1(wt% 92:8)[10nm] / HT-1[24nm] / HT-2[5nm] / H09:BD200(wt% 97:3)[20nm] / Compound of Formula (I)[5nm] / Compound of Formula (II):Compound of Formula (III)(wt% 30:70)[25nm] / E:Li(wt% 99:1)[15nm] / HT-1:D-1(wt% 90:10)[10nm] / HT-1[36nm] / HT-2[5nm] / H09:BD200(wt% 97:3)[20nm] / Compound of Formula (I)[5 [nm] / Compound of Formula (II):Compound of Formula (III) (wt% 30:70) [25nm] / E:Li (wt% 99:1) [15nm] / HT-1:D-1 (wt% 90:10) [10nm] / HT-1 [57nm] / HT-2 [5nm] / H09:BD200 (wt% 97:3) [20nm] / Compound of Formula (I) [5nm] / Compound of Formula (II):Compound of Formula (III) (wt% 30:70) [30nm] / LiQ [1nm] / Yb [2nm] / Ag:Mg (wt% 90:10) [13nm] / HT-3 [65nm].

[0817] Table 5: List of compounds used

[0818]

[0819] Table 6. Performance of organic electroluminescent tandem devices containing compounds of formula (I) in the first electron transport layer and compounds of formula (II) in the second electron transport layer, or comparative compound C-3.

[0820]

[0821] Table 7. Performance of organic electroluminescent tandem devices containing a compound of formula (I) in the first electron transport layer and a mixture of a compound of formula (II) and a compound of formula (III) in the second electron transport layer.

[0822]

[0823]

[0824] Examples 8, 9, and 10 show that if compound (III) is used in the second electron transport layer, the cd / A efficiency is further improved at lower voltages.

[0825] The features disclosed in the foregoing description and dependent claims may be used individually or in any combination thereof as material to implement aspects of the disclosure made in the independent claim in various forms.

Claims

1. An organic light-emitting diode, the organic light-emitting diode comprising an anode, a cathode, a first light-emitting layer, a second light-emitting layer, a first charge-generating layer, and a first electron transport layer stacked together; in -The first charge generation layer is disposed between the first light-emitting layer and the second light-emitting layer; -The first electron transport layer is stacked between the first light-emitting layer and the second light-emitting layer; - The first electron transport layer stack includes a first electron transport layer and a second electron transport layer; -The first electron transport layer comprises a compound of formula (I). (Ar 1 -A c ) a -X b (I); -a and b are independently 1 or 2; -c can be 0 or 1 independently; -Ar 1 Independently selected from C6 to C 60 Aryl or C2 to C 42 Mixed aromatics, -of which each Ar 1 It can be substituted by one or two independent substituents selected from the following: C6 to C6. 12 Aryl, C3 to C 11 Heteroaryl, and C1 to C6 alkyl, D, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, halogen, CN or PY(R) 10 )2, where Y is selected from O, S or Se, and R 10 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or perdeuterated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkoxy; -Among them, Ar 1 Each C6 to C 12 Aryl substituents and Ar 1 Each C3 to C 11 The heteroaryl substituents can be replaced by C1 to C4 alkyl groups or halogens; -A is selected independently from C6 to C. 30 Aryl, -Each A may be substituted by one or two substituents independently selected from the following: C6 to C6 12 Aryl and C1 to C6 alkyl, D, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, halogen, CN or PY(R) 10 )2, where Y is selected from O, S or Se, and R 10 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or perdeuterated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkoxy; -where each C6 to C on A 12 The aryl substituents can be replaced by C1 to C4 alkyl groups or halogens; -X is selected independently from C2 to C. 42 heteroaryl and C6 to C 60 Aryl, - where each X can be substituted by one or two substituents independently selected from the following: C6 to C6 12 Aryl, C3 to C 11 Heteroaryl, and C1 to C6 alkyl, D, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, halogen, CN or PY(R) 10 )2, where Y is selected from O, S or Se, and R 10 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or perdeuterated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkoxy; -where each C6 to C on X 12 aryl substituents and each C3 to C on X 11 The heteroaryl substituents can be replaced by C1 to C4 alkyl groups or halogens; - The molecular dipole moment of the compound of formula (I) is ≥0D and ≤4D; - The second electron transport layer comprises a compound of formula (II). (The 2 ) m -(Z k -G) n (II); -m and n are independently 1 or 2; -k can be 0, 1, or 2 independently; -Ar 2 Independently selected from C2 to C 42 heteroaryl and C6 to C 60 Aryl, -of which each Ar 2 It can be substituted by one or two independent substituents selected from the following: C6 to C6. 12 Aryl, C3 to C 11 Heteroaryl, and C1 to C6 alkyl, D, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, halogen, CN or PY(R) 10 )2, where Y is selected from O, S or Se, and R 10 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or perdeuterated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkoxy; -Among them, Ar 2 Each C6 to C 12 Aryl substituents and Ar 2 Each C3 to C 11 The heteroaryl substituents can be replaced by C1 to C4 alkyl groups or halogens; -Z is selected independently from C6 to C 30 Aryl, - where each Z can be substituted by one or two substituents independently selected from the following: C6 to C6 12 Aryl and C1 to C6 alkyl, D, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, halogen, CN or PY(R) 10 )2, where Y is selected from O, S or Se, and R 10 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or perdeuterated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkoxy; -where each C6 to C on Z 12 The aryl substituents can be replaced by C1 to C4 alkyl groups or halogens; - Choose G such that the dipole moment of the compound G-phenyl is ≥1D and ≤7D; and - The first electron transport layer and the second electron transport layer are free of electro-dopersive agents; The compounds excluded from formula (II) are those with the following formula:

2. The organic light-emitting diode according to claim 1, wherein Ar 1 The group is independently selected from phenyl, naphthyl, anthraceneyl, fluoranthyl, xanthonyl, spiro-xanthonyl, fluorenyl, spiro-fluorenyl, triphenylsilyl, tetraphenylsilyl, or a group having formula (IIa). in - The asterisk "*" indicates the binding site of group (IIa) with A; and -R 1 To R 5 Independently selected from H, C6 to C 12 Aryl and C4 to C 10 Mixed aromatic compounds.

3. The organic light-emitting diode according to claim 1, wherein A is selected from phenylene, naphthylene, biphenylene, and terphenylene, and these groups may be substituted or unsubstituted, respectively.

4. The organic light-emitting diode according to claim 1, wherein X is independently selected from triazinyl, 1,2-diazinyl, 1,3-diazinyl, 1,4-diazinyl, quinazolinyl, benzoquinazolinyl, benzimidazolyl, quinolinyl, benzoquinolinyl, benzoacridyl, dibenzoacridyl, fluoranthyl, anthraceneyl, naphthyl, biphenylideneyl, phenanthrolinel, and dinaphthofuranyl, wherein these groups may be substituted or unsubstituted.

5. The organic light-emitting diode according to claim 1, wherein Ar 2 The group is independently selected from pyridyl, triazinyl, 1,2-diazinyl, 1,3-diazinyl, 1,4-diazinyl, quinazolinyl, benzoquinazolinyl, benzimidazolyl, quinolinyl, benzoquinolinyl, benzoacridyl, dibenzoacridyl, fluoranthyl, anthraceneyl, naphthyl, biphenylideneyl, phenanthrolinel, and dinaphthofuranyl, which may be substituted or unsubstituted.

6. The organic light-emitting diode according to claim 1, wherein... -G is selected from dialkylphosphine oxide, diarylphosphine oxide, alkylarylphosphine oxide, nitriles, benzonitrile, nicotinic nitrile, amide, urea, and C2 to C3 groups. 17 Mixed aromatics; - The corresponding G may include one or more of dialkylphosphine oxide, diarylphosphine oxide, alkylarylphosphine oxide, nitrile, benzonitrile, nicotinic nitrile, amide, urea, and C2 to C3 groups. 17 A heteroaryl-linked substituent, wherein one or more substituents are selected from phenyl, methyl, ethyl and pyridyl.

7. The organic light-emitting diode according to claim 1, wherein G is independently selected from dimethylphosphine oxide, diphenylphosphine oxide, 2-phenyl-1H-benzo[d]imidazolyl, 2-ethyl-1H-benzo[d]imidazolyl, 2-phenylbenzo[h]quinolinyl, pyridyl, 2,2'-bipyridyl, 5-phenylbenzo[4,5]imidazo[1,2-a]quinolinyl, 9-phenyl-1,10-phenanthrolinel and (pyridin-2-yl)imidazo[1,5-a]pyridyl.

8. The organic light-emitting diode of claim 1, wherein G is selected such that the compound G-phenyl is represented by one of the following structures, 9. The organic light-emitting diode according to claim 1, wherein the compound of formula (II) is selected from B-1 to B-25.

10. The organic light-emitting diode of claim 1, wherein the second electron transport layer further comprises compound (III), wherein compound (III) comprises 8 to 13 aromatic or heteroaromatic rings, optionally 8 to 11 aromatic or heteroaromatic rings, optionally 9 or 10 aromatic or heteroaromatic rings.

11. The organic light-emitting diode according to claim 10, wherein the compound (III) comprises 1 to 5 heteroaromatic rings.

12. The organic light-emitting diode according to claim 10, wherein, If the compound (III) contains two or more heteroaromatic rings, the heteroaromatic rings are separated from each other by at least one aromatic ring that does not contain heteroatoms.

13. The organic light-emitting diode according to claim 1, wherein the first electron transport layer is stacked between the first light-emitting layer and the charge-generating layer.

14. The organic light-emitting diode according to claim 1, wherein the first electron transport layer and the second electron transport layer are in direct contact with each other.

15. The organic light-emitting diode according to claim 1, wherein the second electron transport layer is in direct contact with the charge generation layer.

16. The organic light-emitting diode of claim 1, wherein the charge-generating layer comprises a metal, a metal salt, or an organic alkali metal complex, or a mixture thereof.

17. A display device comprising an organic light-emitting diode according to any one of claims 1 to 16, wherein light is emitted through a transparent cathode.

18. A lighting device comprising an organic light-emitting diode according to any one of claims 1 to 16, wherein light is emitted through a transparent cathode.

19. A display device comprising an organic light-emitting diode according to any one of claims 1 to 16, wherein light is emitted through a transparent anode.

20. A lighting device comprising an organic light-emitting diode according to any one of claims 1 to 16, wherein light is emitted through a transparent anode.

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