Semiconductor material, method for preparing a layer of a semiconductor material, organic semiconductor device

Abstract

The present invention relates to a semiconductor material, a method for preparing a layer of the semiconductor material, and an organic semiconductor device comprising the semiconductor material. The invention also relates to a compound.

Description

Technical Field

[0001] The invention relates to a semiconductor material, a method for producing a layer of said semiconductor material and an organic semiconductor device comprising said semiconductor material. The invention also relates to a compound. Background of the Invention

[0003] Organic semiconductor devices such as organic light emitting diodes (OLEDs) as self-luminous devices have wide viewing angles, excellent contrast, fast response, high brightness, excellent operating voltage characteristics, and color reproduction. A typical OLED includes an anode, a hole transport layer HTL, an emission layer EML, an electron transport layer ETL, and a cathode sequentially stacked on a substrate. In this regard, HTL, EML, and ETL are thin films formed of organic compounds.

[0004] When voltage is applied to the anode and cathode, holes injected from the anode move to the EML through the HTL, and electrons injected from the cathode move to the EML through the ETL. Holes and electrons recombine in the EML to generate excitons. When the excitons drop from an excited state to a ground state, light is emitted. The injection and flow of holes and electrons should be balanced so that the OLED having the above structure has excellent efficiency and / or a long life.

[0005] The performance of an organic light emitting diode may be affected by the properties of the organic semiconductor layer, and among other things, by the properties of the organic material of the organic semiconductor layer.

[0006] In particular, there is a need to develop an organic semiconductor layer capable of increasing electron mobility and simultaneously increasing electrochemical stability so that organic semiconductor devices such as organic light emitting diodes can be applied to large-sized flat panel displays.

[0007] In addition, there is a need to develop an organic semiconductor layer that can have an extended service life at higher current density and therefore at higher brightness. In particular, there is a need to develop an organic semiconductor material or semiconductor layer that can reduce the operating voltage of, for example, a mobile display device, which is very important for reducing power consumption and extending battery life.

[0008] Therefore, the object of the present invention is to provide an organic semiconductor device and a semiconductor material and compound for preparing the organic semiconductor device that overcome the disadvantages of the prior art, in particular to provide a compound for use in a semiconductor material and an electronic device containing the same to help improve its performance, in particular in terms of efficiency, operating voltage and / or lifetime. Summary of the invention

[0009] This object is achieved by a semiconductor material comprising a first organic compound, wherein the first organic compound comprises:

[0010] - at least one charge transporting moiety comprising at least one aromatic ring; and

[0011] - at least one group represented by the following formula (1):

[0012] (1)

[0013] in

[0014] - Squiggly line" " represents the position at which the group represented by formula (1) is bonded to the remaining structure of the first organic compound; and

[0015] -R 1 and R 2 Independently selected from H and CH3.

[0016] The charge transport moieties may be independently selected from:

[0017] - heteroaromatic moieties containing at least two heteroatoms;

[0018] - an aryl group comprising at least two, preferably at least three, fused aromatic rings; and

[0019] - a heteroaryl group comprising at least two, preferably at least three, fused aromatic rings.

[0020] The heteroaromatic moiety comprising at least two heteroatoms may be independently selected from diazines, triazines, quinazolines, quinoxalines, benzoquinazolines, benzoquinoxalines, azacarbazoles, azadibenzofurans, azadibenzothiophenes, naphthyridines, benzimidazoles, benzoxazoles, benzothiazoles, imidazopyridines and imidazopyrimidines.

[0021] The aryl group comprising at least two fused aromatic rings may be independently selected from anthracene, phenanthrene and pyrene.

[0022] The heteroaryl group comprising at least two fused aromatic rings may be independently selected from azaanthracene, azaphenanthracene, diazaanthracene, diazaphenanthracene, benzoacridine and dibenzoacridine.

[0023] R 1 and R 2 You can choose the same.

[0024] The first organic compound can be represented by the following formula (2):

[0025] (2)

[0026] in

[0027] R 1 and R 2 Independently selected from H and CH3;

[0028] A is a charge transport moiety; and

[0029] L is a direct bond or a spacer.

[0030] L may be selected from an aromatic subgroup and a heteroaromatic subgroup.

[0031] L may be selected from a phenylene group and a 1,1'-biphenyl-diyl group.

[0032] The semiconductor material may also contain n-type electron dopants.

[0033] The object is also achieved by a method for producing a layer of semiconductor material according to the invention, said method comprising the step of depositing a first organic compound on a solid support.

[0034] The object is also achieved by an organic semiconductor device comprising at least one layer comprising the semiconductor material according to the invention.

[0035] The layer containing a semiconductor material may be an electron transport layer, an electron injection layer, or an electron generation layer.

[0036] The organic semiconductor device may be an organic diode, an organic transistor, an organic solar cell or an organic light emitting diode.

[0037] The object is also achieved by a compound comprising:

[0038] - at least one charge transporting moiety comprising at least one aromatic ring, wherein said charge transporting moieties are independently selected from:

[0039] - a heteroaromatic moiety comprising at least two heteroatoms;

[0040] - an aryl group comprising at least three fused aromatic rings; and

[0041] - a heteroaryl group comprising at least three fused aromatic rings;

[0042] and

[0043] - at least one group represented by the following formula (1):

[0044] (1a)

[0045] in

[0046] - Squiggly line" " represents the position at which the group represented by formula (1) is bonded to the remaining structure of the first organic compound; and

[0047] - and R 1 and R2 Independently selected from H and CH3.

[0048] The object is also achieved by a compound comprising:

[0049] - at least one charge transporting moiety comprising at least one aromatic ring, wherein said charge transporting moieties are independently selected from:

[0050] - a heteroaromatic moiety comprising at least two heteroatoms;

[0051] - an aryl group comprising at least two fused aromatic rings; and

[0052] - a heteroaryl group comprising at least two fused aromatic rings;

[0053] and

[0054] - at least one group represented by the following formula (1):

[0055] (1b)

[0056] in

[0057] - Squiggly line" " represents the position at which the group represented by formula (I) is bonded to the remaining structure of the first organic compound;

[0058] -R 1 and R 2 are independently selected from H and CH3, and

[0059] -R 1 and R 2 At least one of them is CH3.

[0060] Surprisingly, it was found that the semiconductor material according to the invention and the compound according to the invention and the organic semiconductor device according to the invention solve the underlying problem of the invention, so that the device is superior in all respects to the organic electroluminescent devices known from the prior art, in particular in terms of efficiency, operating voltage and / or lifetime. In addition, we found that the compounds according to the invention exhibit particularly good processing properties, in particular good thermal stability and surprisingly low evaporation temperatures during vacuum thermal evaporation (VTE) production.

[0061] Semiconductor Materials

[0062] According to one aspect, the present invention relates to a semiconductor material comprising a first organic compound. The first organic compound comprises: (1.) at least one charge transporting structure part comprising at least one aromatic ring; and (2.) at least one group represented by the following formula (1):

[0063] (1)

[0064] The wavy line " " represents the position where the group represented by formula (1) is bonded to the remaining structure of the first organic compound; and R 1 and R 2 Each is independently selected from H and CH3.

[0065] The charge transport moiety may be a moiety comprising a molecular frontier orbital having a suitable energy level, particularly for transferring charges from the layer comprising the first organic compound to an adjacent layer.

[0066] For example, the first organic compound may be a matrix compound in a layer of an organic semiconductor device. In this case, the frontier orbital energy level of the matrix compound forming the basis of a layer arranged between two electrodes in an organic semiconductor device (i.e., as the main (dominant) compound, e.g., a content of more than 50% by weight or 50% by volume) may be "suitable" in the present invention if the difference between the frontier orbital energy level and the frontier orbital energy level of the matrix compound in an adjacent layer (arranged in contact with the layer containing the first organic compound) is less than 1 eV, preferably less than 0.8 eV, more preferably less than 0.5 eV, and most preferably less than 0.3 eV.

[0067] The frontier orbital determining electron transport in an electron transport material is the lowest unoccupied molecular orbital (LUMO) of the corresponding electron transport host compound. Similarly, the frontier orbital determining hole transport in a hole transport material is the highest occupied molecular orbital (HOMO) of the corresponding hole transport host compound.

[0068] Advantageously, the frontier orbitals of the corresponding host compounds are delocalized on more than two atoms. In one embodiment, if the electron transport portion of the electron transport host comprises a conjugated system of at least four delocalized electrons, preferably at least six delocalized electrons, such frontier orbitals can be provided. Suitable LUMO energy levels in the frontier orbitals formed in such a small delocalized electron system can be adjusted by the presence of one or more heteroatoms, preferably by two or three nitrogen atoms. Examples of such electron transport portions may be diazines, triazines, diazoles, oxadiazoles and triazole portions.

[0069] In another embodiment, the electron transport portion of the electron transport matrix can contain a conjugated system of more than six delocalized electrons, such as ten delocalized electrons or fourteen delocalized electrons. In this embodiment, the requirements for suitable LUMO energy levels can be met in a broad spectrum of carbocyclic and heterocyclic structural moieties comprising at least two fused aromatic rings.

[0070] In addition to at least one charge transporting structure part containing at least one aromatic ring and the group represented by formula (1), the first organic compound may also contain other parts, such as a substituent connected to the charge transporting structure part or a part arranged between a charge transporting structure part containing at least one aromatic ring and the group represented by formula (1). Alternatively, the first organic compound may be composed of at least one charge transporting structure part containing at least one aromatic ring and the group represented by formula (1). In the case where the group represented by formula (1) is bonded to the charge transporting structure part, the wavy line " " may represent a single bond between the group represented by formula (1) and the charge transport structure. In the case where the group represented by formula (1) is bonded to another part of the first organic compound, the wavy line " " may represent a single bond connecting the group represented by formula (1) to the other part of the first organic compound.

[0071] The charge transport moiety may be substituted with one or more substituents independently selected from C6 to C 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 perdeuterated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkoxy, C3 to C 36 Silyl, 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; and each C6 to C 12 The aryl substituent and each C3 to C 11 The heteroaryl substituents may be independently replaced by C1 to C4 alkyl, C3 to C 36 Silyl or halogen substituted.

[0072] The charge transport moieties may be independently selected from C6 to C 12 One or more substituents in the aryl group may or may not exclude C6 to C 12 The presence of other substituents other than aromatic groups. The charge transport moiety can be used as a C 10 The aryl (naphthyl) group may be substituted with one or more substituents, which may or may not exclude C 10 The presence of substituents other than aryl groups.

[0073] The charge transport moieties may be independently selected from:

[0074] - heteroaromatic moieties containing at least two heteroatoms;

[0075] - an aryl group comprising at least two, preferably at least three, fused aromatic rings; and

[0076] - a heteroaryl group comprising at least two, preferably at least three, fused aromatic rings.

[0077] The term "heteroaryl" or "heteroaromatic moiety" may refer to an aromatic heterocycle having at least one heteroatom (or multiple if specifically specified), and all elements of the hydrocarbon heteroaromatic moiety may have a conjugated p orbital. The heteroatom may be independently selected from N, O, S, B, Si, P, Se, preferably selected from N, O and S, more preferably O and N, most preferably N.

[0078] The heteroaromatic moiety containing at least two heteroatoms may be C2 to C 42 Heteroaromatic moieties. Heteroaromatic moieties containing at least two heteroatoms may be C2 to C 39 Heteroaromatic moieties. Heteroaromatic moieties containing at least two heteroatoms may be C2 to C 36 Heteroaromatic moieties. Heteroaromatic moieties containing at least two heteroatoms may be C2 to C 33 Heteroaromatic moieties. Heteroaromatic moieties containing at least two heteroatoms may be C2 to C 30 Heteroaromatic moieties. Heteroaromatic moieties containing at least two heteroatoms may be C2 to C 27 Heteroaromatic moieties. Heteroaromatic moieties containing at least two heteroatoms may be C2 to C 24 Heteroaromatic moieties. Heteroaromatic moieties containing at least two heteroatoms may be C2 to C 21 Heteroaromatic moieties. Heteroaromatic moieties containing at least two heteroatoms may be C2 to C 17 Heteroaromatic moieties. Heteroaromatic moieties containing at least two heteroatoms may be C2 to C 14Heteroaromatic moieties. Heteroaromatic moieties containing at least two heteroatoms may be C2 to C 11 Heteroaromatic moieties. The heteroaromatic moieties comprising at least two heteroatoms may be C2 to C9 heteroaromatic moieties. The heteroaromatic moieties comprising at least two heteroatoms may be C2 to C7 heteroaromatic moieties. The heteroaromatic moieties comprising at least two heteroatoms may be C2 to C5 heteroaromatic moieties. The heteroaromatic moieties comprising at least two heteroatoms may be C3 to C4 heteroaromatic moieties.

[0079] The aromatic heterocyclic moiety containing at least two heteroatoms can be independently selected from diazines, triazines, quinazolines, quinoxalines, benzoquinazolines, benzoquinoxalines, azacarbazoles, azadibenzofurans, azadibenzothiophenes, naphthyridines, benzimidazoles, benzoxazoles, benzothiazoles, imidazopyridines and imidazopyrimidines.

[0080] The aryl group comprising at least two, preferably at least three, fused aromatic rings may be C 10 To C 60 Aryl. The aryl group comprising at least two, preferably at least three fused aromatic rings may be C 10 To C 54 Aryl. The aryl group comprising at least two, preferably at least three fused aromatic rings may be C 10 To C 48 Aryl. The aryl group comprising at least two, preferably at least three fused aromatic rings may be C 10 To C 42 Aryl. The aryl group comprising at least two, preferably at least three fused aromatic rings may be C 10 To C 36 Aryl. The aryl group comprising at least two, preferably at least three fused aromatic rings may be C 10 To C 30 Aryl. The aryl group comprising at least two, preferably at least three fused aromatic rings may be C 10 To C 24 Aryl. The aryl group comprising at least two, preferably at least three fused aromatic rings may be C 10 To C 18 Aryl.

[0081] The aryl group comprising at least two condensed aromatic rings may be independently selected from anthracene, phenanthrene and pyrene. The aryl group comprising at least two condensed aromatic rings may be anthracene.

[0082] The heteroaryl group containing at least two fused aromatic rings may be C6 to C 42 Heteroaryl. A heteroaryl group comprising at least two fused aromatic rings may be C6 to C 39Heteroaryl. A heteroaryl group comprising at least two fused aromatic rings may be C6 to C 36 Heteroaryl. A heteroaryl group comprising at least two fused aromatic rings may be C6 to C 33 Heteroaryl. A heteroaryl group comprising at least two fused aromatic rings may be C6 to C 30 Heteroaryl. A heteroaryl group comprising at least two fused aromatic rings may be C6 to C 27 Heteroaryl. A heteroaryl group comprising at least two fused aromatic rings may be C6 to C 24 Heteroaryl. A heteroaryl group comprising at least two fused aromatic rings may be C6 to C 21 Heteroaryl. A heteroaryl group comprising at least two fused aromatic rings may be C6 to C 17 Heteroaryl. A heteroaryl group comprising at least two fused aromatic rings may be C8 to C 17 Heteroaryl. A heteroaryl group comprising at least two fused aromatic rings may be C8 to C 12 Heteroaryl. The heteroaryl group comprising at least two fused aromatic rings may be a C8 to C9 heteroaryl.

[0083] The heteroaryl group comprising at least two fused aromatic rings may be independently selected from azaanthracene, azaphenanthracene, diazaanthracene, diazaphenanthracene, benzoacridine and dibenzoacridine.

[0084] R 1 and R 2 You can choose the same, that is, R 1 and R 2 Can be H or R 1 and R 2 It can all be CH3.

[0085] The first organic compound can be represented by the following formula (2):

[0086] (2)

[0087] in

[0088] R 1 and R 2 Independently selected from H and CH3;

[0089] A is a charge transport moiety, wherein the charge transport moiety may be unsubstituted or substituted with one or more of the above substituents, and the charge transport moiety may be selected from the above groups; and

[0090] L is a direct bond or a spacer.

[0091] A can be expressed as follows:

[0092]

[0093] Among them, A is in " " is bonded to L at "; and n is 1 or 2.

[0094] A can be represented by one of the following formulas:

[0095] ; ;

[0096] Among them, A is in " ” is bonded to L.

[0097] In the case where L is a spacer, L may be substituted by one or more substituents independently selected from: C6 to C 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 perdeuterated C1 to C6 alkyl, partially or perdeuterated 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 select 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; and each C6 to C 12 The aryl substituent and each C3 to C 11 The heteroaryl substituents may independently be substituted with C1 to C4 alkyl or halogen.

[0098] In the case where L is a spacer, L (i.e., the spacer) may be selected from an aromatic subunit and a heteroaromatic subunit. In the case where L is a spacer, L may be selected from C6 to C 60 Aromatic subunits and C2 to C 42 In the case where L is a spacer, L can be selected from C6 to C 54 Aromatic subunits and C2 to C 39 In the case where L is a spacer, L can be selected from C6 to C 48 Aromatic subunits and C2 to C 36 In the case where L is a spacer, L can be selected from C6 to C 42 Aromatic subunits and C2 to C 33 In the case where L is a spacer, L can be selected from C6 to C36 Aromatic subunits and C2 to C 30 In the case where L is a spacer, L can be selected from C6 to C 30 Aromatic subunits and C2 to C 24 In the case where L is a spacer, L can be selected from C6 to C 24 Aromatic subunits and C2 to C 21 In the case where L is a spacer, L can be selected from C6 to C 18 Aromatic subunits and C2 to C 17 In the case where L is a spacer, L can be selected from C6 to C 12 Aromatic subunits and C2 to C 14 Heteroaromatic subunit.

[0099] In the case where L is a spacer, L (i.e., the spacer) may be an aromatic substituent. In the case where L is a spacer, L may be C6 to C 60 In the case where L is a spacer, L can be C6 to C 54 In the case where L is a spacer, L can be C6 to C 48 In the case where L is a spacer, L can be C6 to C 42 In the case where L is a spacer, L can be C6 to C 36 In the case where L is a spacer, L can be C6 to C 30 In the case where L is a spacer, L can be C6 to C 24 In the case where L is a spacer, L can be C6 to C 18 In the case where L is a spacer, L can be C6 to C 12 Aromatic subunit.

[0100] L may be selected from a phenylene group and a 1,1'-biphenyl-diyl group. L may be a phenylene group. L may be an m-phenylene group.

[0101] According to one embodiment, the present invention relates to a semiconductor material comprising a first organic compound, wherein the first organic compound is represented by the following formula (2):

[0102] (2)

[0103] in

[0104] R 1 and R 2 Independently selected from H and CH3;

[0105] A is a charge transport structure;

[0106] The charge transport moieties are independently selected from:

[0107] - C2 to C containing at least two heteroatoms 42 Heteroaromatic moieties;

[0108] - C containing at least two, preferably at least three fused aromatic rings 10 To C 60 an aryl group; and

[0109] - C6 to C6 containing at least two, preferably at least three fused aromatic rings 42 heteroaryl groups;

[0110] The charge transport moiety may be substituted with one or more substituents independently selected from: C6 to C 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 perdeuterated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkoxy, C3 to C 36 Silyl, 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; and each C6 to C 12 The aryl substituent and each C3 to C 11 The heteroaryl substituents may be independently replaced by C1 to C4 alkyl, C3 to C 36 Silyl or halogen substitution;

[0111] L is a direct bond or a spacer;

[0112] The spacer is C6 to C 60 an aromatic subunit; and

[0113] L may be substituted with one or more substituents independently selected from: C6 to C 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 perdeuterated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkoxy, C3 to C 36 Silyl, 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; and each C6 to C 12 The aryl substituent and each C3 to C 11 The heteroaryl substituents may be independently replaced by C1 to C4 alkyl, C3 to C 36 Silyl or halogen substituted.

[0114] According to one embodiment, the present invention relates to a semiconductor material comprising a first organic compound, wherein the first organic compound is represented by the following formula (2):

[0115] (2)

[0116] in

[0117] R 1 and R 2 Independently selected from H and CH3;

[0118] A is a charge transport structure;

[0119] The charge transport moiety is a C-containing at least two, preferably at least three fused aromatic rings. 10 To C 60 Aryl groups;

[0120] The charge transport moiety may be substituted with one or more substituents independently selected from C6 to C 12 Aryl, wherein the presence of other substituents is not excluded, and the other substituents are independently selected from 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 perdeuterated C1 to C6 alkyl, partially or perdeuterated 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; and each C6 to C 12 The aryl substituent and each C3 to C 11 The heteroaryl substituents may be independently substituted with C1 to C4 alkyl or halogen;

[0121] L is a spacer group;

[0122] The spacer is C6 to C 12 an aromatic subunit; and

[0123] L may be substituted with one or more substituents independently selected from: C6 to C 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 perdeuterated C1 to C6 alkyl, partially or perdeuterated 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; and each C6 to C 12 The aryl substituent and each C3 to C 11 The heteroaryl substituents may independently be substituted with C1 to C4 alkyl or halogen.

[0124] According to one embodiment, the present invention relates to a semiconductor material comprising a first organic compound, wherein the first organic compound is represented by the following formula (2):

[0125] (2)

[0126] in

[0127] R 1 and R 2 Independently selected from H and CH3;

[0128] A is a charge transport structure;

[0129] A is represented by the following formula:

[0130]

[0131] Among them, A is in " " is bonded to L; and n is 1 or 2;

[0132] A may be substituted with one or more substituents independently selected from C6 to C 12 Aryl, wherein the presence of other substituents is not excluded, and the other substituents are independently selected from 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 perdeuterated C1 to C6 alkyl, partially or perdeuterated 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; and each C6 to C 12 The aryl substituent and each C3 to C 11 The heteroaryl substituents may be independently substituted with C1 to C4 alkyl or halogen;

[0133] L is a spacer group;

[0134] The spacer is selected from the group consisting of a phenylene group and a 1,1'-biphenyl-diyl group; and

[0135] L may be substituted with one or more substituents independently selected from: C6 to C12 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 perdeuterated C1 to C6 alkyl, partially or perdeuterated 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; and each C6 to C 12 The aryl substituent and each C3 to C 11 The heteroaryl substituents may independently be substituted with C1 to C4 alkyl or halogen.

[0136] According to one embodiment, the present invention relates to a semiconductor material comprising a first organic compound, wherein the first organic compound is represented by the following formula (2):

[0137] (2)

[0138] in

[0139] R 1 and R 2 Independently selected from H and CH3;

[0140] A is represented by one of the following formulas,

[0141] ; ;

[0142] Among them, A is in " " is bonded to L;

[0143] And L is a phenylene group.

[0144] According to one embodiment, the present invention relates to a semiconductor material comprising a first organic compound, wherein the first organic compound is selected from the following compounds E1 to E44:

[0145] E1 E2 E3 E4 E-5 E-6 E-7 E-8 E-9 E-10 E-11 E-12 E-13 E-14 E-15 E-16 E-17 E-18 E-19 E-20 E-21 E-22 E-23 E-24 E-25 E-26 E-27 E-28 E-29 E-30 E-31 E-32 E-33 E-34 E-35 E-36 E-37 E-38 E-39 E-40 E-41 E-42 E-43 E-44.

[0146] The semiconductor material may be an organic semiconductor material. The semiconductor material may be an electron transport material. The first organic compound may be an electron transport matrix material (electron transport matrix).

[0147] The semiconductor material may contain, in addition to the first organic compound, an electronic dopant, such as an electrical n-type dopant, in particular a redox n-type dopant. An n-type dopant is a compound that, if embedded in an electron transport matrix material, improves the electronic properties of the semiconductor material formed, in particular with respect to electron injection and / or electron conductivity, compared to the pure electron transport matrix material under the same physical conditions.

[0148] In the context of the present invention, "embedded in the electron transport matrix" means uniformly mixed with the electron transport matrix.

[0149] The n-type dopant may be selected from elemental metals, metal salts, metal complexes and organic groups.

[0150] The metal salt may be selected from alkali metal salts and alkaline earth metal salts, and in one embodiment may be selected from salts of the following metals: Li, Na, K, Rb, Cs, Mg, Ca, Sr and Ba. The salt may contain anions selected from the following: halogen anions, complex borate anions, organic phenol anions. In one embodiment, the anions in the salt may be cationic chelated anions such as 8-hydroxyquinolate anions and / or 2-phosphorylphenol anions.

[0151] In one embodiment, the n-type dopant is selected from alkali metal salts and alkali metal complexes; preferably selected from lithium salts and lithium organic complexes; more preferably selected from lithium halides and lithium organic chelates; still more preferably selected from lithium fluoride, lithium quinoline, lithium borate, lithium phenoxide, lithium pyridinolate or lithium complexes with Schiff base ligands; most preferably,

[0152] - The lithium complex has formula II, III or IV:

[0153]

[0154] in

[0155] A1 to A6 are identically or independently selected from CH, CR, N, O;

[0156] R are identical or independently selected from hydrogen, halogen, alkyl or aryl or heteroaryl having 1 to 20 carbon atoms; more preferably A1 to A6 are CH,

[0157] - The borate anion organic ligand is tetrakis(1H-pyrazol-1-yl)borate anion,

[0158] - the phenolate anion is a 2-(pyridin-2-yl)phenolate anion, a 2-phosphoryl-phenolate anion such as a 2-(diphenylphosphoryl)phenolate anion, an imidazophenol anion, a 2-(pyridin-2-yl)phenolate anion or a 2-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenolate anion,

[0159] - The pyridinol anion is 2-(diphenylphosphoryl)pyridin-3-ol anion,

[0160] - The lithium Schiff base has structure 100, 101, 102 or 103:

[0161] .

[0162] According to one embodiment of the present invention, the semiconductor material of the present invention comprises a lithium organic complex or 8-hydroxyquinolate lithium (=LiQ).

[0163] According to one embodiment of the present invention, the semiconductor material comprises a metal, which is preferably selected from alkali metals, alkaline earth metals, rare earth metals and metals of the first transition period Ti, V, Cr and Mn, especially selected from Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, Sm, Eu, Tm, Yb; more preferably selected from Li, Na, K, Rb, Cs, Mg and Yb, still more preferably selected from Li, Na, Cs and Yb, and most preferably selected from Li, Na and Yb.

[0164] The most practical criterion for measuring the strength of an n-type dopant is its redox potential. There is no particular restriction on how negative the redox potential can be.

[0165] The reduction potential of commonly used electron transport substrates in organic semiconductors is generally in the range of about -0.8 V to about -3.1 V when measured by cyclic voltammetry relative to a ferrocene / ferrocene cation reference redox couple; the practically applicable range of redox potential for n-type dopants that can effectively n-dope such substrates is in a slightly wider range of about -0.5 V to about -3.3 V.

[0166] The measurement of redox potential is actually carried out on the corresponding redox couple composed of the reduced state and oxidized state of the same compound.

[0167] In the case where the n-type dopant is an electrically neutral metal complex and / or an electrically neutral organic free radical, the measurement of its redox potential is actually carried out on the redox couple formed by the following substances:

[0168] (i) a neutral metal complex and a cation radical thereof formed by abstracting an electron from the neutral metal complex; or

[0169] (ii) an electrically neutral organic radical and a cation thereof formed by abstracting an electron from the electrically neutral organic radical.

[0170] Preferably, the redox potential of the electrically neutral metal complex and / or electrically neutral organic free radical may have a value more negative than -0.5 V, preferably more negative than -1.2 V, more preferably more negative than -1.7 V, still more preferably more negative than -2.1 V, most preferably more negative than -2.5 V, if measured by cyclic voltammetry relative to a ferrocene / ferrocene cation reference redox couple for the corresponding redox couple consisting of:

[0171] (i) a neutral metal complex and a cation radical thereof formed by abstracting an electron from the neutral metal complex; or

[0172] (ii) an electrically neutral organic radical and a cation thereof formed by abstracting an electron from the electrically neutral organic radical.

[0173] In a preferred embodiment, the redox potential of the n-type dopant is between about 0.5 V more positive and 0.5 V more negative than the reduction potential of the selected electron transporting host.

[0174] Electroneutral metal complexes suitable as n-type dopants may be, for example, strongly reducing complexes of some transition metals in a low oxidation state. As described in more detail in WO 2005 / 086251, particularly strong n-type dopants may be selected, for example, from Cr(II), Mo(II) and / or W(II) guanidine complexes such as W2(hpp)4.

[0175] As described in more detail in EP 1 837 926 B1, WO2007 / 107306 or WO2007 / 107356, the electrically neutral organic free radical suitable as an n-type dopant can be, for example, an organic free radical generated by supplying additional energy from its stable dimer, oligomer or polymer. Under elemental metal, it is understood to be a metal in the state of a pure metal, a metal alloy or in the state of a free atom or a metal cluster. It is understood that the metal deposited by vacuum thermal evaporation from a metallic phase, such as from a pure bulk metal, is volatilized in its elemental form. It is also understood that if the volatilized elemental metal is deposited with a covalent matrix, the metal atoms and / or clusters are embedded in the covalent matrix. In other words, it is understood that any metal-doped covalent material prepared by vacuum thermal evaporation contains a metal that is at least partially in its elemental form.

[0176] For use in consumer electronics, only metals containing stable nuclides or nuclides with very long radioactive decay half-lives are suitable. As an acceptable level of nuclear stability, the nuclear stability of natural potassium can be used.

[0177] In one embodiment, the n-type dopant may be selected from an electropositive metal selected from: alkali metals; alkaline earth metals; rare earth metals; and metals of the first transition period Ti, V, Cr and Mn. Preferably, the n-type dopant may be selected from: Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, Sm, Eu, Tm, Yb; more preferably selected from Li, Na, K, Rb, Cs, Mg and Yb, still more preferably selected from Li, Na, Cs and Yb, most preferably selected from Li, Na and Yb.

[0178] Method for producing a layer of semiconductor material

[0179] The invention also relates to a method for preparing a layer of a semiconductor material according to the invention. The method comprises the step of depositing a first organic compound on a solid support.

[0180] Embodiments described herein with respect to the semiconductor material according to the invention are also embodiments of the method according to the invention.

[0181] Deposition may include the use of:

[0182] - at least one deposition source, preferably two deposition sources, more preferably at least three deposition sources; and / or

[0183] - Deposition by vacuum thermal evaporation; and / or

[0184] - Deposition by solution processing, preferably selected from spin coating, printing, casting and / or slot die coating.

[0185] The solid support may be any layer of an organic semiconductor device on which a semiconductor material is deposited to form a layer, wherein the layer comprising the semiconductor material is directly adjacent to the solid support in the final device.

[0186] According to various embodiments of the present invention, there is provided a method using the following deposition source:

[0187] - a first deposition source to release a first organic compound according to the invention; and

[0188] - a second deposition source to release a metal, a metal salt or an alkali metal or alkaline earth metal complex; or an organic alkali metal or alkaline earth metal complex; or 8-hydroxyquinoline lithium;

[0189] The method comprises the steps of forming an organic semiconductor layer; wherein for an organic light emitting diode (OLED):

[0190] - The organic semiconductor layer is formed by releasing the first organic compound according to the present invention from a first deposition source and releasing the metal, metal salt or alkali metal or alkaline earth metal complex; or organic alkali metal or alkaline earth metal complex; or 8-hydroxyquinolate lithium from a second deposition source.

[0191] 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 a hole injection layer, a hole transport layer or a hole blocking layer between the anode electrode and the first electron transport layer.

[0192] According to various embodiments of the present invention, the method may further include the step of forming an organic light emitting diode (OLED), wherein

[0193] - forming a first anode electrode on the substrate,

[0194] - forming a light emitting layer on the first anode electrode,

[0195] - forming an electron transport layer stack on the light-emitting layer, optionally forming a hole blocking layer on the light-emitting layer and forming an organic semiconductor layer,

[0196] - Finally, the cathode electrode is formed.

[0197] - forming an optional hole injection layer, a hole transport layer and a hole blocking layer in sequence between the first anode electrode and the light-emitting layer,

[0198] - An optional electron injection layer is formed between the organic semiconductor layer and the cathode electrode.

[0199] According to various embodiments of the present invention, the method may further include forming an electron injection layer on the organic semiconductor layer. However, according to various embodiments of the OLED of the present invention, the OLED may not include an electron injection layer.

[0200] According to various embodiments, the OLED may have the following layer structure, wherein the layers have the following order:

[0201] anode, hole injection layer, first hole transport layer, second hole transport layer, light-emitting layer, optional hole blocking layer, layer comprising or consisting of the first organic compound according to the invention, optional electron injection layer and cathode.

[0202] Organic semiconductor devices

[0203] The object is also achieved by an organic semiconductor device comprising at least one layer comprising the semiconductor material according to the invention.

[0204] Embodiments described herein relating to the semiconductor material according to the present invention also relate to embodiments of the organic semiconductor device according to the present invention.

[0205] The layer including the semiconductor material may be an electron transport layer, an electron injection layer, or an electron generation layer.

[0206] The organic semiconductor device may be an organic diode, an organic transistor, an organic solar cell or an organic light emitting diode, and in particular may be an organic light emitting diode.

[0207] According to the present invention, the organic semiconductor device may further comprise other layers in addition to the layers mentioned above, in particular, in addition to the electron transport layer and / or electron injection layer and / or electron generation layer comprising or consisting of the semiconductor material according to the present invention. Exemplary embodiments of the various layers are described below:

[0208] Base

[0209] The substrate can be any substrate commonly used to manufacture electronic devices such as organic light emitting diodes. If light is to be emitted through the substrate, the substrate 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 either a transparent material or an opaque material, such as a glass substrate, a plastic substrate, a metal substrate, or a silicon substrate.

[0210] Anode electrode

[0211] The first electrode or the second electrode included in the organic semiconductor device of the present invention can be an anode electrode. The anode electrode can be formed by depositing or sputtering a material for forming the anode electrode. The material used to form the anode electrode can be a high work function material, thereby facilitating hole injection. The anode material can also be selected from a low work function material (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. The anode electrode can also be formed using a metal or a metal alloy, and the metal is typically silver (Ag) or gold (Au).

[0212] Hole injection layer

[0213] The hole injection layer (HIL) can be formed on the anode electrode by vacuum deposition, spin coating, printing, casting, slot die coating, Langmuir-Blodgett (LB) deposition, etc. When the HIL is formed using vacuum deposition, the deposition conditions may vary depending on the compound used to form the HIL and the desired structure and thermal properties of the HIL. However, in general, the vacuum deposition conditions may include a deposition temperature of 100° C. to 500° C., a ... -8 Up to 10 -3 Torr pressure (1 Torr equals 133.322 Pa) and a deposition rate of 0.1 nm / sec to 10 nm / sec.

[0214] When the HIL is formed using spin coating or printing, the coating conditions may vary depending on the compound used to form the HIL and the desired structure and thermal properties of the HIL. For example, the 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. After coating, heat treatment is performed to remove the solvent.

[0215] The HIL may be formed of any compound that is generally used to form a HIL. Examples of the compound that can be used to form the 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-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), and polyaniline / poly(4-styrenesulfonate (PANI / PSS).

[0216] The HIL may include or consist of a p-type dopant and the p-type dopant may be selected from tetrafluoro-tetracyanoquinodimethane (F4TCNQ), 2,2'-(perfluoronaphthalene-2,6-diylidene)dimalononitrile or 2,2',2''-(cyclopropane-1,2,3-triylidene)tris(2-(p-cyanotetrafluorophenyl)acetonitrile), but is not limited thereto. The HIL may be selected from a hole transport host compound doped with a p-type dopant. Typical examples of known doped hole transport materials are: copper phthalocyanine (CuPc) doped with tetrafluoro-tetracyanoquinodimethane (F4TCNQ), the HOMO level of the copper phthalocyanine (CuPc) being about -5.2 eV and the LUMO level of the tetrafluoro-tetracyanoquinodimethane (F4TCNQ) being about -5.2 eV; zinc phthalocyanine (ZnPc) doped with F4TCNQ (HOMO=-5.2 eV); α-NPD (N,N'-bis(naphthalene-1-yl)-N,N'-bis(phenyl)-benzidine) doped with F4TCNQ; α-NPD doped with 2,2'-(perfluoronaphthalene-2,6-diylidene) dimalononitrile. The concentration of the p-type dopant can be selected from 1 wt% to 20 wt%, more preferably from 3 wt% to 10 wt%.

[0217] The thickness of the HIL may be within a range of about 1 nm to about 100 nm, for example, within a range of about 1 nm to about 25 nm. When the thickness of the HIL is within this range, the HIL may have excellent hole injection characteristics without substantially deteriorating driving voltage.

[0218] Hole transport layer

[0219] The hole transport layer (HTL) can be formed on the HIL by 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 conditions of deposition and coating can be similar to those of forming the HIL. However, the conditions of vacuum or solution deposition may vary depending on the compound used to form the HTL.

[0220] The HTL may be formed of any compound commonly used to form the HTL. For example, compounds that can be suitably used are disclosed 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 the HTL 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(naphthalene-1-yl)-N,N'-diphenylbenzidine (α-NPD); and triphenylamine compounds such as 4,4',4''-tri(N-carbazolyl)triphenylamine (TCTA). Among these compounds, TCTA can transport holes and inhibit the diffusion of excitons into the EML.

[0221] The thickness of the HTL may be in the range of about 5 nm to about 250 nm, preferably about 10 nm to about 200 nm, further about 20 nm to about 190 nm, further about 40 nm to about 180 nm, further about 60 nm to about 170 nm, further about 80 nm to about 160 nm, further about 100 nm to about 160 nm, further about 120 nm to about 140 nm. The preferred thickness of the HTL may be 170 nm to 200 nm.

[0222] When the thickness of the HTL is within this range, the HTL may have excellent hole transport characteristics without substantially deteriorating driving voltage.

[0223] Electron blocking layer

[0224] The function of the electron blocking layer (EBL) is to prevent electrons from being transferred from the light-emitting layer to the hole transport layer, thereby limiting the electrons in the light-emitting layer. Thus, the efficiency, operating voltage and / or life are improved. Typically, the electron blocking layer comprises a triarylamine compound. The LUMO energy level of the triarylamine compound may be closer to the vacuum energy level than the LUMO energy level of the hole transport layer. Compared with the HOMO energy level of the hole transport layer, the electron blocking layer may have a HOMO energy level that is further away from the vacuum energy level. The thickness of the electron blocking layer may be selected between 2 nm and 20 nm.

[0225] If the electron blocking layer has a high triplet energy level, it can also be described as a triplet controlling layer.

[0226] If a phosphorescent green or blue emitting layer is used, the function of the triplet control layer is to reduce the quenching of the triplet state. Thus, a 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 the triplet energy level of the phosphorescent emitter in the adjacent emitting layer. Suitable compounds for triplet control layers, in particular triarylamine compounds, are described in EP 2 722 908 A1.

[0227] Photoactive Layer (PAL)

[0228] The photoactive layer converts electric current into photons or converts photons into electric current.

[0229] The PAL can be formed on the HTL by vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, etc. When the PAL is formed by vacuum deposition or spin coating, the conditions of deposition and coating may be similar to those of forming the HIL. However, the conditions of deposition and coating may vary depending on the compound used to form the PAL.

[0230] The photoactive layer may not contain the compound of formula (1).

[0231] The photoactive layer can be a light emitting layer or a light absorbing layer.

[0232] Emitting Layer (EML)

[0233] The EML can be formed on the 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 conditions of deposition and coating may be similar to those of forming the HIL. However, the conditions of deposition and coating may vary depending on the compound used to form the EML.

[0234] The light-emitting layer may not contain the compound of formula (1).

[0235] 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-di(naphthalene-2-yl)anthracene (ADN), 4,4',4''-tri(carbazole-9-yl)-triphenylamine (TCTA), 1,3,5-tri(N-phenylbenzimidazol-2-yl)benzene (TPBI), 3-tert-butyl-9,10-di-2-naphthylanthracene (TBADN), distyrylarene (DSA), and bis(2-(2-hydroxyphenyl)benzothiazole)zinc (Zn(BTZ)2).

[0236] The emitter dopant may be a phosphorescent or fluorescent emitter. Phosphorescent emitters and emitters emitting via a thermally activated delayed fluorescence (TADF) mechanism may be preferred due to their higher efficiency. The emitter may be a small molecule or a polymer.

[0237] Examples of red emitter dopants are PtOEP, Ir(piq)3 and Btp2Ir(acac), but are not limited thereto. These compounds are phosphorescent emitters, however, fluorescent red emitter dopants may also be used.

[0238] Examples of phosphorescent green emitter dopants are Ir(ppy)3 (ppy=phenylpyridine), Ir(ppy)2(acac), Ir(mpyp)3.

[0239] Examples of phosphorescent blue emitter dopants are: F2Irpic, (F2ppy)2Ir(tmd) and Ir(dfppz)3; and trifluorene. 4,4'-bis(4-diphenylaminophenylvinyl)biphenyl (DPAVBi), 2,5,8,11-tetra-tert-butylperylene (TBPe) are examples of fluorescent blue emitter dopants.

[0240] The amount of the luminophore dopant may be in the range of about 0.01 parts by weight to about 50 parts by weight based on 100 parts by weight of the host. Alternatively, the luminescent layer may be composed of a luminescent polymer. The EML may have a thickness of about 10 nm to about 100 nm, for example, about 20 nm to about 60 nm. When the thickness of the EML is within this range, the EML may have excellent light emission without causing substantial damage to the driving voltage.

[0241] Hole Blocking Layer (HBL)

[0242] The hole blocking layer (HBL) can be formed on the EML by using vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, etc. to prevent holes from diffusing into the ETL. When the EML contains a phosphorescent dopant, the HBL can also have a triplet exciton blocking function. The hole blocking layer can be an organic semiconductor layer of the present invention, which contains or consists of a compound of the present invention represented by the general formula (1) as defined above.

[0243] HBL can also be named as assisted ETL or a-ETL.

[0244] When vacuum deposition or spin coating is used to form HBL, the conditions of deposition and coating can be similar to those for forming HIL. However, the conditions of deposition and coating can vary with the compound used to form HBL. Any compound commonly used to form HBL can be used. Examples of compounds used to form HBL include oxadiazole derivatives, triazole derivatives, and phenanthroline derivatives.

[0245] The thickness of the HBL may be in a 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 may have excellent hole blocking properties without substantially deteriorating driving voltage.

[0246] The hole blocking layer may also be described as an a-ETL or an auxiliary ETL.

[0247] According to one embodiment, a hole-blocking layer is arranged between the at least one photoactive layer and the layer comprising or consisting of the semiconductor material according to the invention.

[0248] According to one embodiment, a hole blocking layer is arranged between at least one photoactive layer and a layer comprising or consisting of a semiconductor material according to the invention, wherein the layer comprising a semiconductor material according to the invention comprises, in addition to the first organic compound, an additive, which may be an n-type dopant.

[0249] According to one embodiment, a hole blocking layer is arranged between at least one photoactive layer and a layer comprising or consisting of a semiconductor material according to the invention, wherein the layer comprising a semiconductor material according to the invention also comprises a metal, a metal compound or a metal-organic complex, or a metal or lithium-organic complex.

[0250] According to one embodiment, the hole blocking layer is arranged between at least one photoactive layer and the layer comprising or consisting of the semiconductor material according to the invention, wherein the layer comprising or consisting of the semiconductor material according to the invention also comprises a metal.

[0251] Electron Transport Layer (ETL)

[0252] The semiconductor device according to the present invention may include an electron transport layer (ETL). According to a preferred embodiment of the present invention, the electron transport layer may be a layer including or consisting of the semiconductor material according to the present invention.

[0253] According to various embodiments, the OLED may comprise an electron transport layer or an electron transport layer stack comprising at least a first electron transport layer and at least a second electron transport layer.

[0254] By properly adjusting the energy level of a specific layer of the ETL, the injection and transport of electrons can be controlled, and holes can be effectively blocked, thereby allowing the OLED to have a long lifespan.

[0255] The electron transport layer of the semiconductor device may include a first organic compound as defined above as an organic electron transport matrix (ETM) material. In addition to the first organic compound or as a substitute thereof, the electron transport layer may also include other ETM materials known in the prior art. Similarly, the electron transport layer may include a first organic compound as the only electron transport matrix material. In the case where the organic semiconductor device of the present invention includes more than one electron transport layer, the first organic compound may be included in only one electron transport layer, in more than one electron transport layer, or in all electron transport layers. According to the present invention, in addition to the ETM material, the electron transport layer may also include at least one additive as defined below.

[0256] In addition, the electron transport layer may include one or more dopants. The additive may be an n-type dopant. The additive may 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 may be one selected from the following: Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, La, Ce, Sm, Eu, Tb, Dy and Yb. In another embodiment, the n-type dopant may be one selected from the following: Cs, K, Rb, Mg, Na, Ca, Sr, Eu and Yb. In one embodiment, the alkali metal compound may be 8-hydroxyquinoline lithium (LiQ), lithium tetrakis (1H-pyrazol-1-yl) borate or 2-(diphenylphosphoryl) phenolate lithium. There is no particular restriction on suitable compounds of ETM (compounds that can be used in addition to the compounds of the present invention shown in the general formula (1) defined above). In one embodiment, the electron transport matrix compound is composed of covalently bonded atoms. Preferably, the electron transport matrix compound comprises a conjugated system of at least 6, more preferably at least 10 delocalized electrons. In one embodiment, the conjugated system of delocalized electrons may be contained in an aromatic or heteroaromatic moiety, as disclosed in, for example, documents EP 1 970 371 A1 or WO 2013 / 079217 A1.

[0257] Electron injection layer (EIL)

[0258] An optional EIL may be formed on the ETL, preferably directly on the electron transport layer, which facilitates the injection of electrons from the cathode. Examples of materials forming the EIL include 8-hydroxyquinoline lithium (LiQ), LiF, NaCl, CsF, Li2O, BaO, Ca, Ba, Yb, and Mg known in the art. The deposition and coating conditions for forming the EIL are similar to those for forming the HIL, but the deposition and coating conditions may vary depending on the material used to form the EIL.

[0259] The thickness of the EIL may 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 may have satisfactory electron injection performance without substantially deteriorating driving voltage.

[0260] Charge Generation Layer (CGL)

[0261] The charge generation layer (CGL) may include a p-type charge generation layer (p-CGL) and an n-type charge generation layer (n-CGL). An intermediate layer may be disposed between the p-CGL and the n-CGL.

[0262] Typically, the charge generation layer is a pn junction connecting an n-type charge generation layer (electron generation layer) and a hole generation layer. The n-side of the pn junction generates electrons and injects them into the adjacent layer in the anode direction. Similarly, the p-side of the pn junction generates holes and injects them into the adjacent layer in the cathode direction.

[0263] The charge generation layer is used in tandem and stacked devices, for example, in a tandem or stacked OLED comprising two or more light-emitting layers between two electrodes. In a tandem or stacked OLED comprising two light-emitting layers, the n-type charge generation layer provides electrons for a first light-emitting layer arranged near the anode, while the hole generation layer provides holes for a second light-emitting layer arranged between the first light-emitting layer and the cathode.

[0264] Suitable host materials for the hole generation layer may be materials conventionally used as hole injection and / or hole transport host materials. Moreover, conventional materials may be used as p-type dopants for the hole generation layer. For example, the p-type dopant may be one selected from the following: tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), derivatives of tetracyanoquinodimethane, axialene derivatives, iodine, FeCl3, FeF3, and SbCl5. In addition, the host may be one selected from the following: N,N'-di(naphthalene-1-yl)-N,N-diphenylbenzidine (NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1-biphenyl-4,4'-diamine (TPD), and N,N',N'-tetranaphthylbenzidine (TNB). The p-type charge generation layer may be composed of CNHAT.

[0265] The n-type charge generation layer may be a layer comprising a semiconductor material according to the present invention or consisting of a semiconductor material according to the present invention. The n-type charge generation layer may be a layer of a pure n-type dopant such as a metal, or may be composed of an organic matrix material doped with an n-type dopant. In one embodiment, the n-type dopant may 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 may be one selected from the following: Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, La, Ce, Sm, Eu, Tb, Dy, and Yb. More specifically, the n-type dopant may be one selected from the following: Li, Cs, K, Rb, Mg, Na, Ca, Sr, Eu, and Yb. Suitable matrix materials for the electron generation layer may be materials conventionally used as matrix materials for electron injection or electron transport layers. The matrix material may be, for example, one selected from the following: a triazine compound, a hydroxyquinoline derivative such as tris (8-hydroxyquinoline) aluminum, a benzoxazole derivative, and a silacyclopentane derivative.

[0266] The hole generation layer is arranged in direct contact with the n-type charge generation layer.

[0267] According to one aspect of the present invention, the organic semiconductor layer is disposed between the first and second light emitting layers and further includes an n-type dopant.

[0268] According to one aspect of the present invention, the organic semiconductor layer is disposed between the first and second light emitting layers and further contains a metal.

[0269] According to one aspect of the present invention, the organic semiconductor layer is disposed between the first and second light-emitting layers, and further comprises a metal selected from the group consisting of alkali metals, alkaline earth metals, and rare earth metals.

[0270] According to one aspect of the present invention, a layer comprising or consisting of a semiconductor material according to the present invention is arranged between the first and second light-emitting layers, and other layers comprising or consisting of a semiconductor material according to the present invention are arranged between the second light-emitting layer and the cathode.

[0271] According to one aspect of the present invention, a layer containing a semiconductor material according to the present invention or consisting of a semiconductor material according to the present invention is arranged between the first and second light-emitting layers, and other layers containing a semiconductor material according to the present invention or consisting of a semiconductor material according to the present invention are arranged between the second light-emitting layer and the cathode; wherein the layer containing a semiconductor material according to the present invention or consisting of a semiconductor material according to the present invention further contains an n-type dopant.

[0272] According to one aspect of the present invention, a layer containing a semiconductor material according to the present invention or consisting of a semiconductor material according to the present invention is arranged between a first and a second light-emitting layer, and other layers containing a semiconductor material according to the present invention or consisting of a semiconductor material according to the present invention are arranged between the second light-emitting layer and the cathode; the other layers containing a semiconductor material according to the present invention or consisting of a semiconductor material according to the present invention further contain an n-type dopant.

[0273] According to one aspect of the present invention, a layer containing a semiconductor material according to the present invention or consisting of a semiconductor material according to the present invention is arranged between a first and a second light-emitting layer, and other layers containing a semiconductor material according to the present invention or consisting of a semiconductor material according to the present invention are arranged between the second light-emitting layer and the cathode; the layer containing a semiconductor material according to the present invention or consisting of a semiconductor material according to the present invention further contains an n-type dopant, and other layers containing a semiconductor material according to the present invention or consisting of a semiconductor material according to the present invention further contain an n-type dopant.

[0274] According to one aspect of the present invention, a layer containing a semiconductor material according to the present invention or consisting of a semiconductor material according to the present invention is arranged between a first and a second light-emitting layer, and other layers containing a semiconductor material according to the present invention or consisting of a semiconductor material according to the present invention are arranged between the second light-emitting layer and the cathode; wherein the layer containing a semiconductor material according to the present invention or consisting of a semiconductor material according to the present invention further contains a metal, and other layers containing a semiconductor material according to the present invention or consisting of a semiconductor material according to the present invention further contain an n-type dopant.

[0275] Method for preparing an organic semiconductor device

[0276] The present invention also relates to a method for producing an organic semiconductor device according to the present invention, said method comprising the method for producing a semiconductor material according to the present invention.

[0277] Organic Light Emitting Diodes

[0278] The organic semiconductor device according to the present invention may be an organic light emitting device.

[0279] According to one aspect of the present invention, an organic light emitting diode (OLED) is provided, which comprises: a substrate; an anode electrode formed on the substrate; a hole injection layer, a hole transport layer, a light emitting layer, a layer comprising or consisting of a semiconductor material according to the present invention, and a cathode electrode.

[0280] According to another aspect of the present invention, an OLED is provided, which includes: a substrate; an anode electrode formed on the substrate; a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, a layer including or consisting of the semiconductor material according to the present invention, and a cathode electrode.

[0281] According to another aspect of the present invention, an OLED is provided, which includes: a substrate; an anode electrode formed on the substrate; a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, a layer containing or consisting of the semiconductor material according to the present invention, an electron injection layer and a cathode electrode.

[0282] According to various embodiments of the present invention, OLED layers may be provided disposed between the above layers, on the substrate, or on the top electrode.

[0283] According to one aspect, an OLED may include a layer structure of a substrate arranged adjacent to an anode electrode, the anode electrode being arranged adjacent to a first hole injection layer, the first hole injection layer being arranged adjacent to a first hole transport layer, the first hole transport layer being arranged adjacent to a first electron blocking layer, the first electron blocking layer being arranged adjacent to a first light-emitting layer, the first light-emitting layer being arranged adjacent to a first electron transport layer, the first electron transport layer being arranged adjacent to an n-type charge generation layer, the n-type charge generation layer being arranged adjacent to the hole generation layer, the hole generation layer being arranged adjacent to a second hole transport layer, the second hole transport layer being arranged adjacent to a second electron blocking layer, the second electron blocking layer being arranged adjacent to a second light-emitting layer, and an optional electron transport layer and / or an optional injection layer being arranged between the second light-emitting layer and the cathode electrode.

[0284] The semiconductor layer according to the present invention, ie, the layer including the first organic compound, may be an electron transport layer, a first electron transport layer, an n-type charge generation layer and / or a second electron transport layer.

[0285] For example, according to Figure 2The OLED can be formed by the following method: an anode (120), a hole injection layer (130), a hole transport layer (140), an electron blocking layer (145), a light emitting layer (150), a hole blocking layer (155), an electron transport layer (160), an electron injection layer (180) and a cathode electrode (190) are sequentially formed on a substrate (110).

[0286] According to another aspect of the present invention, there is provided an organic semiconductor device, the organic semiconductor device comprising at least one organic light emitting device according to any embodiment described in the entire application, preferably, the electronic device comprises an organic light emitting diode in one embodiment described in the entire application. More preferably, the electronic device is a display device.

[0287] In one embodiment, the organic semiconductor device according to the present invention including a layer including or consisting of the semiconductor material according to the present invention may further include a layer including a radialene compound and / or a quinodimethane compound.

[0288] In one embodiment, the axialene compound and / or quinodimethane compound can be substituted with one or more halogen atoms and / or one or more electron withdrawing groups. The electron withdrawing group can be selected from nitrile group, haloalkyl group, or from perhaloalkyl group, or from perfluoroalkyl group. Other examples of electron withdrawing groups can be acyl group, sulfonyl group or phosphoryl group.

[0289] Alternatively, the acyl group, sulfonyl group and / or phosphoryl group may contain halogenated and / or perhalogenated hydrocarbon groups. In one embodiment, the perhalogenated hydrocarbon group may be a perfluoro hydrocarbon group. Examples of perfluoro hydrocarbon groups may be perfluoromethyl, perfluoroethyl, perfluoropropyl, perfluoroisopropyl, perfluorobutyl, perfluorophenyl, perfluorotolyl; Examples of sulfonyl groups containing halogenated hydrocarbon groups may be trifluoromethylsulfonyl, pentafluoroethylsulfonyl, pentafluorophenylsulfonyl, heptafluoropropylsulfonyl, nonafluorobutylsulfonyl, etc.

[0290] In one embodiment, the radialene and / or quinodimethane compound may be included in a hole injection layer, a hole transport layer, and / or a hole generation layer.

[0291] In one embodiment, the radialene compound may have the formula (XX) and / or the quinodimethane compound may have the formula (XXIa) or (XXIb):

[0292]

[0293] where (as an exception to the above description) R 1 , R 2 , R 3 , R4 , R 5 , R 6 , R 7 , R 8 , R 11 , R 12 , R 15 , R 16 , R 20 , R 21 are 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 Independently selected from H, halogen and the above-mentioned electron withdrawing groups.

[0294] According to one embodiment of the present invention, a layer comprising or consisting of a semiconductor material according to the present invention is adjacent to a layer comprising a compound of the formula (XX), (XXIa) or (XXIb).

[0295] According to one embodiment of the present invention, the layer comprising or consisting of the semiconductor material according to the present invention is in direct contact with the layer comprising the compound of the formula (XX), (XXIa) or (XXIb).

[0296] Compound

[0297] According to another aspect, the present invention relates to a compound comprising:

[0298] - at least one charge transporting moiety comprising at least one aromatic ring, wherein said charge transporting moieties are independently selected from:

[0299] - a heteroaromatic moiety comprising at least two heteroatoms;

[0300] - an aryl group comprising at least two, preferably at least three, fused aromatic rings; and

[0301] - a heteroaryl group comprising at least two, preferably at least three, fused aromatic rings;

[0302] and

[0303] - at least one group represented by the following formula (1)

[0304] (1)

[0305] in

[0306] - Squiggly line" " represents the position at which the group represented by formula (1) is bonded to the remaining structure of the first organic compound; and

[0307] -R 1 and R 2 Independently selected from H and CH3.

[0308] In addition to at least one charge transporting structure part containing at least one aromatic ring and the group represented by formula (1), the compound may also contain other parts, such as a substituent connected to the charge transporting structure part or a part arranged between a charge transporting structure part containing at least one aromatic ring and the group represented by formula (1). Alternatively, the compound may be composed of at least one charge transporting structure part containing at least one aromatic ring and the group represented by formula (1). In the case where the group represented by formula (1) is bonded to the charge transporting structure part, the wavy line " " can represent a single bond between the group represented by formula (1) and the charge transport structure. In the case where the group represented by formula (1) is bonded to another part of the compound, the wavy line " " may represent a single bond connecting the group represented by formula (1) to other parts of the compound.

[0309] The charge transport moiety may be substituted with one or more substituents independently selected from C6 to C 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 perdeuterated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkoxy, C3 to C 36 Silyl, 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; and each C6 to C 12 The aryl substituent and each C3 to C 11 The heteroaryl substituents may be independently replaced by C1 to C4 alkyl, C3 to C 36 Silyl or halogen substituted.

[0310] The charge transport moieties may be independently selected from C6 to C 12 One or more substituents in the aryl group may or may not exclude C6 to C 12 The presence of other substituents other than aromatic groups. The charge transport moiety can be used as a C 10 The aryl (naphthyl) group may be substituted with one or more substituents, which may or may not exclude C 10 The presence of substituents other than aryl groups.

[0311] The term "heteroaryl" or "heteroaromatic moiety" may refer to an aromatic heterocycle having at least one heteroatom (or multiple if specifically specified), and all elements of the hydrocarbon heteroaromatic moiety may have a conjugated p orbital. The heteroatom may be independently selected from N, O, S, B, Si, P, Se, preferably selected from N, O and S, more preferably O and N, most preferably N.

[0312] The heteroaromatic moiety containing at least two heteroatoms may be C2 to C 42 Heteroaromatic moieties. Heteroaromatic moieties containing at least two heteroatoms may be C2 to C 39 Heteroaromatic moieties. Heteroaromatic moieties containing at least two heteroatoms may be C2 to C 36 Heteroaromatic moieties. Heteroaromatic moieties containing at least two heteroatoms may be C2 to C 33 Heteroaromatic moieties. Heteroaromatic moieties containing at least two heteroatoms may be C2 to C 30 Heteroaromatic moieties. Heteroaromatic moieties containing at least two heteroatoms may be C2 to C 27 Heteroaromatic moieties. Heteroaromatic moieties containing at least two heteroatoms may be C2 to C 24 Heteroaromatic moieties. Heteroaromatic moieties containing at least two heteroatoms may be C2 to C 21 Heteroaromatic moieties. Heteroaromatic moieties containing at least two heteroatoms may be C2 to C 17 Heteroaromatic moieties. Heteroaromatic moieties containing at least two heteroatoms may be C2 to C 14 Heteroaromatic moieties. Heteroaromatic moieties containing at least two heteroatoms may be C2 to C 11 Heteroaromatic moieties. The heteroaromatic moieties comprising at least two heteroatoms may be C2 to C9 heteroaromatic moieties. The heteroaromatic moieties comprising at least two heteroatoms may be C2 to C7 heteroaromatic moieties. The heteroaromatic moieties comprising at least two heteroatoms may be C2 to C5 heteroaromatic moieties. The heteroaromatic moieties comprising at least two heteroatoms may be C3 to C4 heteroaromatic moieties.

[0313] The aromatic heterocyclic moiety may contain at least two heteroatoms. The heteroaromatic moiety may be independently selected from diazine, triazine, quinazoline, quinoxaline, benzoquinazoline, benzoquinoxaline, azacarbazole, azadibenzofuran, azadibenzothiophene, naphthyridine, benzimidazole, benzothiazole, benzoimidazolyl, imidazopyridine and imidazopyrimidine.

[0314] The aryl group comprising at least two, preferably at least three, fused aromatic rings may be C 10 To C 60 Aryl. The aryl group comprising at least two, preferably at least three fused aromatic rings may be C 10 To C 54 Aryl. The aryl group comprising at least two, preferably at least three fused aromatic rings may be C 10 To C 48 Aryl. The aryl group comprising at least two, preferably at least three fused aromatic rings may be C 10 To C 42 Aryl. The aryl group comprising at least two, preferably at least three fused aromatic rings may be C 10 To C 36 Aryl. The aryl group comprising at least two, preferably at least three fused aromatic rings may be C 10 To C 30 Aryl. The aryl group comprising at least two, preferably at least three fused aromatic rings may be C 10 To C 24 Aryl. The aryl group comprising at least two, preferably at least three fused aromatic rings may be C 10 To C 18 Aryl.

[0315] The aryl group comprising at least two condensed aromatic rings may be independently selected from anthracene, phenanthrene and pyrene. The aryl group comprising at least two condensed aromatic rings may be anthracene.

[0316] The heteroaryl group containing at least two fused aromatic rings may be C6 to C 42 Heteroaryl. A heteroaryl group comprising at least two fused aromatic rings may be C6 to C 39 Heteroaryl. A heteroaryl group comprising at least two fused aromatic rings may be C6 to C 36 Heteroaryl. A heteroaryl group comprising at least two fused aromatic rings may be C6 to C 33 Heteroaryl. A heteroaryl group comprising at least two fused aromatic rings may be C6 to C 30 Heteroaryl. A heteroaryl group comprising at least two fused aromatic rings may be C6 to C 27 Heteroaryl. A heteroaryl group comprising at least two fused aromatic rings may be C6 to C24 Heteroaryl. A heteroaryl group comprising at least two fused aromatic rings may be C6 to C 21 Heteroaryl. A heteroaryl group comprising at least two fused aromatic rings may be C6 to C 17 Heteroaryl. A heteroaryl group comprising at least two fused aromatic rings may be C8 to C 17 Heteroaryl. A heteroaryl group comprising at least two fused aromatic rings may be C8 to C 12 Heteroaryl. The heteroaryl group comprising at least two fused aromatic rings may be a C8 to C9 heteroaryl.

[0317] The heteroaryl group comprising at least two fused aromatic rings may be independently selected from azaanthracene, azaphenanthracene, diazaanthracene, diazaphenanthracene, benzoacridine and dibenzoacridine.

[0318] R 1 and R 2 You can choose the same, that is, R 1 and R 2 Can be H or R 1 and R 2 It can all be CH3.

[0319] The compound according to the present invention can be represented by the following formula (2):

[0320] (2)

[0321] in

[0322] R 1 and R 2 Independently selected from H and CH3;

[0323] A is a charge transport moiety, wherein the charge transport moiety may be unsubstituted or substituted with one or more of the above substituents, and the charge transport moiety may be selected from the above groups; and

[0324] L is a direct bond or a spacer.

[0325] A can be expressed as follows:

[0326]

[0327] Among them, A is in " " is bonded to L at "; and n is 1 or 2.

[0328] A can be represented by one of the following formulas:

[0329] ; ;

[0330] Among them, A is in " ” is bonded to L.

[0331] In the case where L is a spacer, L (i.e., the spacer) may be selected from an aromatic subunit and a heteroaromatic subunit. In the case where L is a spacer, L may be selected from C6 to C 60 Aromatic subunits and C2 to C 42 In the case where L is a spacer, L can be selected from C6 to C 54 Aromatic subunits and C2 to C 39 In the case where L is a spacer, L can be selected from C6 to C 48 Aromatic subunits and C2 to C 36 In the case where L is a spacer, L can be selected from C6 to C 42 Aromatic subunits and C2 to C 33 In the case where L is a spacer, L can be selected from C6 to C 36 Aromatic subunits and C2 to C 30 In the case where L is a spacer, L can be selected from C6 to C 30 Aromatic subunits and C2 to C 24 In the case where L is a spacer, L can be selected from C6 to C 24 Aromatic subunits and C2 to C 21 In the case where L is a spacer, L can be selected from C6 to C 18 Aromatic subunits and C2 to C 17 In the case where L is a spacer, L can be selected from C6 to C 12 Aromatic subunits and C2 to C 14 Heteroaromatic subunit.

[0332] In the case where L is a spacer, L (i.e., the spacer) may be an aromatic substituent. In the case where L is a spacer, L may be C6 to C 60 In the case where L is a spacer, L can be C6 to C 54 In the case where L is a spacer, L can be C6 to C 48 In the case where L is a spacer, L can be C6 to C 42 In the case where L is a spacer, L can be C6 to C 36 In the case where L is a spacer, L can be C6 to C 30 In the case where L is a spacer, L can be C6 to C 24 In the case where L is a spacer, L can be C6 to C 18 In the case where L is a spacer, L can be C6 to C 12 Aromatic subunit.

[0333] L may be selected from a phenylene group and a 1,1'-biphenyl-diyl group. L may be a phenylene group. L may be a meta-phenylene group.

[0334] According to one embodiment, the present invention relates to a compound represented by the following formula (2):

[0335] (2)

[0336] in

[0337] R 1 and R 2 Independently selected from H and CH3;

[0338] A is a charge transport structure;

[0339] The charge transport moieties are independently selected from:

[0340] - C2 to C containing at least two heteroatoms 42 Heteroaromatic moieties;

[0341] - C containing at least two, preferably at least three fused aromatic rings 10 To C 60 an aryl group; and

[0342] - C6 to C6 containing at least two, preferably at least three fused aromatic rings 42 heteroaryl groups;

[0343] The charge transport moiety may be substituted with one or more substituents independently selected from: C6 to C 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 perdeuterated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkoxy, C3 to C 36 Silyl, 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; and each C6 to C 12 The aryl substituent and each C3 to C11 The heteroaryl substituents may be independently replaced by C1 to C4 alkyl, C3 to C 36 Silyl or halogen substitution;

[0344] L is a direct bond or a spacer;

[0345] The spacer is C6 to C 60 an aromatic subunit; and

[0346] L may be substituted with one or more substituents independently selected from: C6 to C 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 perdeuterated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkoxy, C3 to C 36 Silyl, 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; and each C6 to C 12 The aryl substituent and each C3 to C 11 The heteroaryl substituents may be independently replaced by C1 to C4 alkyl, C3 to C 36 Silyl or halogen substituted.

[0347] According to one embodiment, the present invention relates to a compound represented by the following formula (2):

[0348] (2)

[0349] in

[0350] R 1 and R 2 Independently selected from H and CH3;

[0351] A is a charge transport structure;

[0352] The charge transport moiety is a C-containing at least two, preferably at least three fused aromatic rings. 10 To C 60 Aryl groups;

[0353] The charge transporting structure part is substituted with one or more substituents independently selected from C6 to C 12 Aryl, wherein the presence of other substituents is not excluded, and the other substituents are independently selected from 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 perdeuterated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkoxy, C3 to C 36 Silyl, 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; and each C6 to C 12 The aryl substituent and each C3 to C 11 The heteroaryl substituents may be independently replaced by C1 to C4 alkyl, C3 to C 36 Silyl or halogen substitution;

[0354] L is a spacer group;

[0355] The spacer is C6 to C 12 an aromatic subunit; and

[0356] L may be substituted with one or more substituents independently selected from: C6 to C 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 perdeuterated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkoxy, C3 to C 36 Silyl, 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 12heteroaryl, 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; and each C6 to C 12 The aryl substituent and each C3 to C 11 The heteroaryl substituents may be independently replaced by C1 to C4 alkyl, C3 to C 36 Silyl or halogen substituted.

[0357] According to one embodiment, the present invention relates to a compound represented by the following formula (2):

[0358] (2)

[0359] in

[0360] R 1 and R 2 Independently selected from H and CH3;

[0361] A is a charge transport structure;

[0362] A is represented by the following formula:

[0363]

[0364] Among them, A is in " " is bonded to L; and n is 1 or 2;

[0365] A may be substituted with one or more substituents independently selected from C6 to C 12 Aryl, wherein the presence of other substituents is not excluded, and the other substituents are independently selected from 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 perdeuterated C1 to C6 alkyl, partially or perdeuterated 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; and each C6 to C 12 The aryl substituent and each C3 to C11 The heteroaryl substituents may be independently substituted with C1 to C4 alkyl or halogen;

[0366] L is a spacer group;

[0367] The spacer is selected from the group consisting of a phenylene group and a 1,1'-biphenyl-diyl group; and

[0368] L may be substituted with one or more substituents independently selected from: C6 to C 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 perdeuterated C1 to C6 alkyl, partially or perdeuterated 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; and each C6 to C 12 The aryl substituent and each C3 to C 11 The heteroaryl substituents may independently be substituted with C1 to C4 alkyl or halogen.

[0369] According to one embodiment, the present invention relates to a compound represented by the following formula (2):

[0370] (2)

[0371] in

[0372] R 1 and R 2 Independently selected from H and CH3;

[0373] A is represented by one of the following formulas,

[0374] ; ;

[0375] Among them, A is in " " is bonded to L;

[0376] And L is a phenylene group.

[0377] According to one embodiment, the present invention relates to a compound selected from the group consisting of the following compounds E1 to E44:

[0378] E1 E2 E3 E4 E-5 E-6 E-7 E-8 E-9 E-10 E-11 E-12 E-13 E-14 E-15 E-16 E-17 E-18 E-19 E-20 E-21 E-22 E-23 E-24 E-25 E-26 E-27 E-28 E-29 E-30 E-31 E-32 E-33 E-34 E-35 E-36 E-37 E-38 E-39 E-40 E-41 E-42 E-43 E-44.

[0379] General Definition

[0380] In this specification, when no definition is provided otherwise, "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. The term "alkyl" as used herein should encompass straight chain as well as branched and cyclic alkyl groups. For example, C3-alkyl groups may be selected from n-propyl and isopropyl. Similarly, C4-alkyl groups include n-butyl, sec-butyl and tert-butyl. Similarly, C6-alkyl groups include n-hexyl and cyclohexyl.

[0381] As used herein, unless otherwise expressly stated, an asterisk " ” indicates the binding position where the corresponding labeled moiety is bonded to another moiety.

[0382] C n The subscript number n in relates to the total number of carbon atoms in the corresponding alkyl, arylene, heteroarylene or aryl group.

[0383] As used herein, the term "aryl" or "aryl substituent" should cover: phenyl (C6-aryl); fused aromatic compounds such as naphthalene, anthracene, phenanthrene, tetracene, etc. Also covered are biphenyl and oligophenyl or polyphenyl such as terphenyl, phenyl-substituted biphenyl, phenyl-substituted terphenyl (e.g., phenyl group of tetraphenyl), etc. "aryl substituent", correspondingly "heteroaryl substituent" refers to a group connected to two other parts. In this specification, the term "aryl group" or "aryl substituent group" may refer to a group comprising at least one hydrocarbon aromatic part, and all elements of the hydrocarbon aromatic part may have a p orbital forming a conjugation, such as a phenyl group, a naphthyl group, an anthracene group, a phenanthrene group, a pyrenyl group, a fluorenyl group, etc. Also included are spiro compounds, in which two aromatic parts are connected to each other by spiro atoms, such as 9,9'-spiro two [9H-fluorene] base. Aryl or aryl substituent groups may include monocyclic or condensed ring polycyclic (i.e., sharing the connection of adjacent carbon atom pairs) functional groups.

[0384] As used herein, the term "heteroaryl" refers to an aryl group in which at least one carbon atom is replaced by a heteroatom. The term "heteroaryl" may refer to an aromatic heterocycle having at least one heteroatom, and all elements of the hydrocarbon heteroaromatic portion may have a p orbital forming a conjugation. The heteroatom may be selected from N, O, S, B, Si, P, Se, preferably selected from N, O and S. The heteroaryl subunit ring may include at least 1 to 3 heteroatoms. Preferably, the heteroaryl subunit ring may include at least 1 to 3 heteroatoms independently selected from N, S and / or O. As in the case of "aryl" / "aryl subunit", the term "heteroaryl" includes, for example, spiro compounds in which two aromatic moieties are interconnected, such as spiro[fluorene-9,9'-xanthene]. Other exemplary heteroaryl groups are diazines, triazines, dibenzofurans, dibenzothiophenes, acridines, benzoacridines and dibenzoacridines, etc.

[0385] As used herein, the term "alkenyl" refers to a group containing a carbon-carbon double bond -CR 1 =CR 2 R 3 .

[0386] As used herein, the term "perhalogenated" refers to a hydrocarbyl group in which all of the hydrogen atoms of the hydrocarbyl group are replaced by halogen (F, Cl, Br, I) atoms.

[0387] As used herein, the term "alkoxy" refers to a structural fragment of the formula -OR, wherein R is a hydrocarbon group, preferably an alkyl group or a cycloalkyl group.

[0388] As used herein, the term "thioalkyl" refers to a structural fragment of the formula -SR, wherein R is a hydrocarbon group, preferably an alkyl group or a cycloalkyl group.

[0389] C n The subscript number n in -heteroaryl refers only to the number of carbon atoms in addition to the number of heteroatoms. In this context, it is clear that the C3 heteroaryl group is an aromatic compound containing three carbon atoms such as pyrazole, imidazole, oxadiazole, thiazole, etc.

[0390] As used herein, the term "heteroaryl" shall include pyridine, quinoline, benzoquinoline, quinazoline, benzoquinazoline, pyrimidine, pyrazine, triazine, benzimidazole, benzothiazole, benzo[4,5]thieno[3,2-d]pyrimidine, carbazole, xanthene, phenazine, benzoacridine, dibenzoacridine, and the like.

[0391] In this specification, the term single bond means a direct bond.

[0392] As used herein, the term "fluorinated" refers to a hydrocarbon group in which at least one hydrogen atom contained in the hydrocarbon group is replaced by a fluorine atom. A fluorinated group in which all of its hydrogen atoms are replaced by fluorine atoms is called a perfluorinated group and is specifically represented by the term "fluorinated".

[0393] According to the present invention, a group is "substituted" by another group if one of the hydrogen atoms contained in the group is replaced by another group, wherein the other group is a substituent.

[0394] According to the present invention, in the formula showing the following bonding conditions, The group A may be bonded to any suitable bonding position. In the case where the bonds of A span more than one ring The group A may be bonded to any suitable bonding position of the respective ring spanned by the bond.

[0395] According to the invention, the expression "between" with respect to a layer between two other layers does not exclude the presence of other layers that may be arranged between the one layer and one of the two other layers. According to the invention, the expression "in direct contact" with respect to two layers in direct contact with each other means that no other layer is arranged between these two layers. A layer deposited on top of another layer is considered to be in direct contact with this layer.

[0396] The term "sandwiched in contact" refers to an arrangement of three layers wherein the middle layer is in direct contact with two adjacent layers.

[0397] With regard to the electron transport layer stack of the invention, the compounds mentioned in the experimental part are most preferred.

[0398] A lighting device can be any device used for illumination, radiation, signaling or projection. They are classified accordingly as lighting, radiation, signaling and projection devices. A lighting device is usually composed of the following elements: a source of optical radiation; a device that transmits the radiation flux into space in the desired direction; and a housing that connects the components into a single device and protects the radiation source and the optical transmission system from environmental damage and influences.

[0399] According to another aspect, the organic electroluminescent device according to the invention comprises two or three or more light-emitting layers. OLEDs comprising more than one light-emitting layer are also referred to as tandem OLEDs or stacked OLEDs.

[0400] Organic electroluminescent devices (OLEDs) can be bottom or top emitting devices. Organic electroluminescent devices (OLEDs) can emit light through a transparent anode or through a transparent cathode.

[0401] A further aspect relates to a device comprising at least one organic electroluminescent device (OLED).

[0402] Devices comprising organic light emitting diodes are, for example, displays or lighting panels.

[0403] For the present invention, for the following defined terms, these definitions shall apply unless a different definition is given in the claims or elsewhere in this specification.

[0404] In the context of this specification, the term "different" or "different" in relation to a host material means that the host materials differ in their structural formula.

[0405] The terms "OLED" and "organic light emitting diode" are used concurrently and have the same meaning. The term "organic electroluminescent device" as used herein may include an organic light emitting diode as well as an organic light emitting transistor (OLET).

[0406] As used herein, "weight percent", "weight %", "wt.-%" and variations thereof refer to a composition, component, substance or agent expressed as the weight of the component, substance or agent of the respective electron transport layer divided by the total weight of its respective electron transport layer and multiplied by 100. It is understood that the amount of the total weight percentage of all components, substances and agents of the respective electron transport layer and electron injection layer is selected in such a way that it does not exceed 100 weight %.

[0407] As used herein, "volume percent", "volume %", "vol.-%" and variations thereof refer to expressing a composition, component, substance or agent as the volume of the component, substance or agent of the respective electron transport layer divided by the total volume of its respective electron transport layer and multiplied by 100. It is understood that the amount of the total volume percentage of all components, substances and agents of the cathode layer is selected in such a way that it does not exceed 100 volume %.

[0408] Whether or not explicitly stated, it is assumed herein that all numerical values ​​are modified by the term "about". As used herein, the term "about" refers to the variation in quantity that can occur. Whether or not modified by the term "about", the claims include equivalents of the quantities.

[0409] It must be noted that, as used in this specification and the appended claims, the singular forms "a," "an," "the," and "said" include plural referents unless the content clearly dictates otherwise.

[0410] The terms "does not contain", "does not contain", and "does not include" do not exclude impurities. Impurities have no technical influence on the purpose achieved by the present invention.

[0411] In the context of this specification, the term "substantially non-luminescent" or "non-luminescent" means that the compound or layer contributes less than 10%, preferably less than 5%, to the visible light luminescence spectrum from the device relative to the visible light luminescence spectrum. The visible light luminescence spectrum is the luminescence spectrum with a wavelength of about ≥380 nm to about ≤780 nm.

[0412] Preferably, the organic semiconductor layer comprising the compound of formula (1) is substantially non-emissive or non-emissive.

[0413] The operating voltage, also called U, is 10 mA / cm2. 2 ) is measured in volts (V).

[0414] Candela efficiency per ampere, also known as cd / A efficiency, is measured at 10 milliamperes per square centimeter (mA / cm 2 ) is measured in candela per ampere.

[0415] External quantum efficiency, also called EQE, is measured in percent (%).

[0416] The color space is described by the coordinates CIE-x and CIE-y (International Commission on Illumination 1931). CIE-y is particularly important for blue luminescence. The smaller the CIE-y, the darker the blue. Efficiency values ​​are compared at the same CIE-y.

[0417] The highest occupied molecular orbital (also called HOMO) and the lowest unoccupied molecular orbital (also called LUMO) are measured in electron volts (eV).

[0418] The terms "OLED", "organic light emitting diode", "organic light emitting device", "organic optoelectronic device" and "organic light emitting diode" are used concurrently and have the same meaning.

[0419] The terms "useful life" and "lifetime" are used concurrently and have the same meaning.

[0420] The anode and cathode may be described as anode electrode / cathode electrode or anode electrode / cathode electrode or anode electrode layer / cathode electrode layer.

[0421] Room temperature, also called ambient temperature, is 23°C.

[0422] Hereinafter, the embodiments are illustrated in more detail with reference to the examples. However, the present invention is not limited to the following examples. Reference will now be made in detail to the exemplary aspects. BRIEF DESCRIPTION OF THE DRAWINGS

[0423] The components described above and the components claimed for protection and used in the embodiments according to the invention are not limited by any special exceptions in terms of their size, shape, material selection and technical concept, so that selection criteria known in the relevant field can be applied without restriction.

[0424] Other details, features and advantages of the subject matter of the invention are disclosed in the dependent claims and in the description of the following drawings, which show preferred embodiments according to the invention in an exemplary manner. However, any embodiment does not necessarily represent the full scope of the invention, and therefore reference is made to the claims and this document to interpret the scope of the invention. It should be understood that the above general description and the following detailed description are only exemplary and explanatory, and are intended to further explain the invention as claimed.

[0425] Figure 1 is a schematic cross-sectional view of an organic semiconductor device according to an exemplary embodiment of the present invention;

[0426] Figure 2 is a schematic cross-sectional view of an organic light emitting diode (OLED) according to an exemplary embodiment of the present invention;

[0427] Figure 3 is a schematic cross-sectional view of an OLED according to an exemplary embodiment of the present invention;

[0428] Figure 4 is a schematic cross-sectional view of an OLED including a charge generation layer and two light-emitting layers according to an exemplary embodiment of the present invention.

[0429] Hereinafter, the accompanying drawings will be illustrated in more detail in conjunction with the embodiments. However, the present invention is not limited to the following accompanying drawings.

[0430] Here, when a first element is referred to as being formed or disposed "on" a second element, the first element may be disposed directly on the second element, or one or more other elements may be disposed therebetween. When a first element is referred to as being formed or disposed "directly" on a second element, no other elements are disposed therebetween.

[0431] Figure 1 1 is a schematic cross-sectional view of an organic semiconductor device 100 according to an exemplary embodiment of the present invention. The organic semiconductor device 100 includes a substrate 110, an anode 120, a photoactive layer (PAL) 125, and a layer 160 including or consisting of a semiconductor material according to the present invention. The layer 160 including or consisting of a semiconductor material according to the present invention is formed on the PAL 125. On the organic semiconductor layer 160, a cathode 190 is provided.

[0432] Figure 2 1 is a schematic cross-sectional view of an organic light emitting diode (OLED) 100 according to an exemplary embodiment of the present invention. The OLED 100 includes a substrate 110, an anode 120, a hole injection layer (HIL) 130, a hole transport layer (HTL) 140, an emission layer (EML) 150, and an electron transport layer (ETL) 160. The electron transport layer (ETL) 160 is formed on the EML 150. On the electron transport layer (ETL) 160, an electron injection layer (EIL) 180 is disposed. A cathode 190 is directly disposed on the electron injection layer (EIL) 180.

[0433] As an alternative to a single electron transport layer 160, a stack of electron transport layers (ETL) may optionally be used.

[0434] Figure 3 is a schematic cross-sectional view of an OLED 100 according to another exemplary embodiment of the present invention. Figure 3 and Figure 2 The difference is that Figure 3 The OLED 100 includes an electron blocking layer (EBL) 145 and a hole blocking layer (HBL) 155 .

[0435] refer to Figure 3 , the OLED 100 includes a substrate 110, an anode 120, a hole injection layer (HIL) 130, a hole transport layer (HTL) 140, an electron blocking layer (EBL) 145, an emission layer (EML) 150, a hole blocking layer (HBL) 155, an electron transport layer (ETL) 160, an electron injection layer (EIL) 180 and a cathode electrode 190.

[0436] Preferably, the organic semiconductor layer including the compound of formula (1) may be an ETL.

[0437] Figure 4 is a schematic cross-sectional view of an OLED 100 according to another exemplary embodiment of the present invention. Figure 4 and Figure 3 The difference is that Figure 4 The OLED 100 further includes a charge generation layer (CGL) and a second light emitting layer (151).

[0438] See also Figure 4, the OLED 100 includes a substrate 110, an anode 120, a first hole injection layer (HIL) 130, a first hole transport layer (HTL) 140, a first electron blocking layer (EBL) 145, a first light emitting layer (EML) 150, a first hole blocking layer (HBL) 155, a first electron transport layer (ETL) 160, an n-type charge generation layer (n-type CGL) 185, a hole generation layer (p-type charge generation layer; p-type GCL) 135, a second hole transport layer (HTL) 141, a second electron blocking layer (EBL) 146, a second light emitting layer (EML) 151, a second hole blocking layer (EBL) 156, a second electron transport layer (ETL) 161, a second electron injection layer (EIL) 181 and a cathode 190.

[0439] Preferably, the layer comprising or consisting of the semiconductor material according to the present invention may be an n-type CGL.

[0440] Preferably, the layer including or consisting of the semiconductor material according to the present invention may be the first ETL, the n-type CGL and / or the second ETL.

[0441] Despite Figure 1 , Figure 2 , Figure 3 and Figure 4 Although not shown in the figure, a sealing layer may be further formed on the cathode electrode 190 to seal the OLED 100. In addition, various other variations may be applied thereto.

[0442] Hereinafter, the embodiments will be illustrated in more detail with reference to Examples. However, the present invention is not limited to the following Examples. DETAILED DESCRIPTION

[0443] The invention is further illustrated by the following examples, which are merely illustrative and non-binding.

[0444] Experimental Section

[0445] Melting point

[0446] The melting point (mp) was determined as the peak temperature from the DSC curve of the above-mentioned TGA-DSC measurement or from a separate DSC measurement (Mettler Toledo DSC822e, the sample was heated from room temperature to complete melting at a heating rate of 10 K / min under a pure nitrogen flow. An amount of 4 mg to 6 mg of sample was placed in a 40 µL Mettler Toledo aluminum pan with a lid in which a hole of <1 mm was punched).

[0447] Glass transition temperature

[0448] The glass transition temperature (Tg) was measured as described in DIN EN ISO 11357, published in March 2010, in a Mettler Toledo DSC 822e differential scanning calorimeter under nitrogen and using a heating rate of 10 K / min.

[0449] Standard starting temperature

[0450] The standard onset temperature (TRO) is determined by loading 100 mg of the compound into a VTE source. As VTE source, organic material point sources provided by Kurt J. Lesker Company (www.Lesker.com) or CreaPhys GmbH (http: / / www.creaphys.com) can be used. -5 The VTE source is heated at a constant rate of 15 K / min at a pressure of 10 mbar and the temperature inside the source is measured with a thermocouple. The evaporation of the compound is detected with a QCM detector, which detects the deposition of the compound on the quartz crystal of the detector. The deposition rate on the quartz crystal is measured in Å / s. To determine the standard onset temperature, the deposition rate is plotted against the VTE source temperature. The standard onset is the temperature at which significant deposition occurs on the QCM detector. To obtain accurate results, the VTE source is heated and cooled 3 times and only the results of the second and third runs are used to determine the standard onset temperature.

[0451] In order to well control the evaporation rate of the organic compound, the standard starting temperature may be in the range of 200°C to 255°C. If the standard starting temperature is below 200°C, the evaporation may be too fast and thus difficult to control. If the standard starting temperature is above 255°C, the evaporation rate may be too low, which may result in a low takt time, and the organic compound in the VTE source may decompose due to long-term exposure to high temperature.

[0452] The standard onset temperature is an indirect measure of the volatility of a compound. The higher the standard onset temperature, the lower the volatility of the compound.

[0453] Measurement of OLED performance

[0454] To evaluate the performance of the OLED devices, the current efficiency was measured at 20°C. The current-voltage characteristics were determined using a Keithley 2635 source measurement unit by supplying a voltage in V and measuring the current in mA flowing through the device under test. The voltage applied to the device was varied in the range of 0 V to 10 V in steps of 0.1 V. Likewise, the luminance-voltage characteristics and CIE coordinates were measured in cd / m² for each voltage value using an Instrument Systems CAS-140CT array spectrometer (calibrated by Deutsche Akkreditierungsstelle (DAkkS)). 2 By interpolating the brightness-voltage and current-voltage characteristics, the brightness at 10 mA / cm 2 cd / A efficiency when

[0455] If applicable, use a Keithley 2400 source meter at ambient conditions (20°C) and 30 mA / cm 2 The device lifetime LT is measured and recorded in hours.

[0456] The brightness of the device is measured using a calibrated photodiode. The lifetime LT is defined as the time until the brightness of the device decreases to 97% of its initial value.

[0457] Synthesis Procedure

[0458] Diisobutyl (3-(10-(naphthalen-2-yl) anthracene-9-yl) phenyl) phosphine oxide (E1)

[0459]

[0460] (10-(Naphthalene-2-yl)anthracen-9-yl)boronic acid (6.44 g, 18.5 mmol), (3-bromophenyl)diisobutylphosphine oxide (6.45 g, 20.3 mmol), tetrakis(triphenylphosphine)palladium(0) (0.641 g, 0.555 mmol) and potassium carbonate (7.67 g, 55.5 mmol) were placed in a Schlenk flask under N2 and dissolved in a mixture of dioxane (120 mL) and water (30 mL) saturated with N2. The mixture was heated to 80°C for 23 hours. After removing the volatiles under reduced pressure, the resulting solid was extracted with CHCl3, and the filtrate was washed with water and dried over magnesium sulfate. The mixture was separated by flash column chromatography on a short silica gel column using CHCl2 and CHCl2 / MeOH (97:3) as eluents. The fractions containing the product were combined, the volume was concentrated, and the product was precipitated by adding n-hexane. The solid was purified by stirring with cyclohexane for 2 hours and drying under vacuum. The yield was 4.4 g (44%).

[0461] (3-(9,10-Di(naphthalene-2-yl)anthracen-2-yl)phenyl)diisobutylphosphine oxide (E2)

[0462]

[0463] 2-(9,10-Di(naphthalene-2-yl)anthracen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (14.0 g, 25.2 mmol), (3-bromophenyl)diisobutylphosphine oxide (9.60 g, 30.2 mmol) and tetrakis(triphenylphosphine)palladium(0) were added to a flask containing N2-saturated dioxane (160 mL) and potassium carbonate (10.4 g, 75.5 mmol) in water (40 mL). The mixture was heated to 75°C for 44 hours. After cooling to room temperature, the volatiles were removed under reduced pressure. The semisolid residue was extracted with CHCl3 and washed with water. The organic phase was dried over magnesium sulfate, filtered through silica gel and reduced in volume under vacuum. Flash column chromatography was then performed on a short silica gel column using CHCl2 and CHCl / MeOH (97:3) as eluents. The fractions containing the product were combined, the volume was reduced, and a pale yellow solid was precipitated by the addition of n-hexane. The solid was recrystallized from toluene to give the product (8.9 g, 53%).

[0464] (3-(10-(Naphthalen-2-yl)anthracen-9-yl)phenyl)dineopentylphosphine oxide (E3)

[0465]

[0466] (10-(Naphthalen-2-yl)anthracen-9-yl)boronic acid (9.18 g, 26.4 mmol), (3-bromophenyl)di-neopentylphosphine oxide (7.00 g, 20.3 mmol), tetrakis(triphenylphosphine)palladium(0) (0.703 g, 0.608 mmol) and potassium carbonate (8.40 g, 60.8 mmol) were placed in a Schlenk flask under N2 and dissolved in a mixture of dioxane (120 mL) and water (30 mL) saturated with N2. The mixture was heated to 85°C and maintained for 16 hours. A light-colored solid precipitated upon cooling, which was filtered off when the reaction mixture reached 30°C and subsequently washed with 1,4-dioxane. The solid was dissolved in CH2Cl2, filtered through a pad of Florisil and concentrated to dryness under vacuum. The residue was redissolved in CH2Cl2 (50 mL) at 50°C and n-hexane (75 mL) was added. The volume decreased by about 25 mL, resulting in the precipitation of the product as a light yellow solid, which was dried under vacuum. Yield 4.2 g (37%).

[0467] (3-(9,10-Di(naphthalene-2-yl)anthracen-2-yl)phenyl)dineopentylphosphine oxide (E4)

[0468]

[0469] Potassium carbonate (8.29 g, 60.0 mmol) was dissolved in 130 mL of deionized water, and argon was introduced into the solution for 30 minutes. Glyme (200 mL) was degassed with argon in a 500 mL three-necked round-bottom flask for 30 minutes. Then, 3-bromophenyl (di-neopentyl) phosphine oxide (7.25 g, 21.0 mmol), (9,10-di(naphthalene-2-yl) anthracene-2-yl) boronic acid (9.49 g, 20.0 mmol) and [Pd(PPh3)4] (694 mg, 0.60 mmol) were added to the flask under argon. The degassed potassium carbonate solution was added with a syringe, and the reaction mixture was heated to 85°C and maintained for 12 hours.

[0470] After cooling to room temperature, the obtained precipitate was collected by filtration, washed with water and methanol, and dried under vacuum at 40 ° C to obtain a light yellow solid. Using CH2Cl2 and CH2Cl2 / MeOH (98:2) as eluents, the product was purified by rapid column chromatography on silica gel. Finally, by impregnating in a mixture of petroleum ether, diethyl ether and CH2Cl2 and drying under high vacuum, the desired product was obtained as a light yellow powder. Yield 9.14 g (66%).

[0471] (3-(4-(4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl)naphthalen-1-yl)phenyl)dineopentylphosphine oxide (E-19)

[0472]

[0473] (3-Bromophenyl)dineopentylphosphine oxide (18.6 g, 53.8 mmol), 2,4-diphenyl-6-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-1-yl)phenyl)-1,3,5-triazine (34.5 g, 56.5 mmol) and potassium carbonate (18.6 g, 134.6 mmol) were suspended in 1,4-dioxane (650 ml) and water (110 ml) in a Schlenk flask, and the mixture was purged with N2. Subsequently, tetrakis(triphenylphosphine)palladium(0) (622 mg, 0.54 mmol) was added, and the mixture was heated at reflux for 60 hours. After cooling, the resulting precipitate was collected by filtration and washed with water and methanol. The solid was then purified with a short silica gel column using CH2Cl2 and CH2Cl2 / MeOH (9:1) as eluents. Evaporation of the solvent from the appropriate fractions gave the desired product (35.0 g, 93%), ESI-MS: m / z = 700 [M+H].

[0474] (3-(4-(4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl)naphthalen-1-yl)phenyl)dineopentylphosphine oxide (E-27)

[0475]

[0476] (4-Bromophenyl)dineopentylphosphine oxide (9.93 g, 28.8 mmol), 2,4-diphenyl-6-(3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-1-yl)phenyl)-1,3,5-triazine (17.0 g, 30.2 mmol) and potassium carbonate (9.9 g, 71.9 mmol) were placed in a Schlenk flask, and the air was replaced with N2. Subsequently, tetrakis(triphenylphosphine)palladium(0) (332 mg, 0.30 mmol) was added, followed by 1,4-dioxane (220 ml) and water (40 ml). The mixture was then purged with N2 and heated to reflux for 16 hours. After cooling to room temperature, the resulting precipitate was collected by filtration and washed with water and methanol. The solid was then purified using a short silica gel column using CH2Cl2 and CH2Cl2 / MeOH (9:1) as eluents. Evaporation of the solvent from the appropriate fractions gave the desired product (13.4 g, 67%), ESI-MS: m / z = 700 [M+H]+ .

[0477] (4'-(4-(6-(naphthalen-1-yl)-[1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazine-2-yl)-[1,1'-biphenyl]-3-yl)dineopentylphosphine oxide (E-29)

[0478]

[0479] (3-Bromophenyl)dineopentylphosphine oxide (10.3 g, 29.9 mmol), 2-(6-(naphthalen-1-yl)-[1,1'-biphenyl]-3-yl)-4-phenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (20.0 g, 31.4 mmol) and potassium carbonate (10.3 g, 74.7 mmol) were suspended in 1,4-dioxane (220 ml) and water (40 ml) in a Schlenk flask, and the mixture was purged with N2. Subsequently, tetrakis(triphenylphosphine)palladium(0) (345 mg, 0.30 mmol) was added, and the mixture was heated to reflux for 60 hours. After cooling, the aqueous phase was separated and discarded, and the organic phase was evaporated to dryness under reduced pressure. The crude solid was purified by flash column chromatography using CH2Cl2 and CH2Cl2 / MeOH (9:1) as eluents, followed by recrystallization from toluene to give the pure product (16.4 g, 71%), ESI-MS: m / z = 611 [M+H] + .

[0480] (3-(9,10-Di(naphthalene-2-yl)anthracen-2-yl)phenyl)diethylphosphine oxide (A2)

[0481]

[0482] The flask was flushed with nitrogen and charged with 2-(9,10-di(naphthalene-2-yl)anthracen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (20.0 g, 35.9 mmol), (3-bromophenyl)diethylphosphine oxide (11.3 g, 43.1 mmol), Pd(PPh3)4 (1.3 g, 1.1 mmol) and K2CO3 (14.9 g, 107.8 mmol). A mixture of degassed 1,4-dioxane / water (4:1, 270 mL) was added, and the reaction mixture was heated to reflux overnight under a nitrogen atmosphere. After cooling to room temperature, the solvent was removed under reduced pressure, and the crude product was extracted with a CH2Cl2 / K2CO3 aqueous solution mixture, then dried over MgSO4 and filtered through a silica gel pad. The impurities were rinsed with additional CH2Cl2, and the product was then rinsed with CH2Cl2 / methanol (98:2, 800 mL). The filtrate was dried under reduced pressure, then dissolved in DCM, stirred with n-hexane overnight, and the solid was isolated by suction filtration. i Further purification was achieved by recrystallization from PrOH / acetonitrile and toluene to give 9.4 g (43%) of a yellow solid after drying. Final purification was achieved by sublimation. HPLC / ESI-MS: m / z=611 [M+H] + .

[0483] (3-(9,10-Di(naphthalene-2-yl)anthracen-2-yl)phenyl)diisopropylphosphine oxide (A3)

[0484]

[0485] In a nitrogen flushed flask, (3-bromophenyl)diisopropylphosphine oxide (7.7 g, 26.6 mmol, 1.3 eq.), 2-(9,10-di(naphthalene-2-yl)anthracen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (11.4 g, 20.5 mmol) were dissolved with Pd(PPh3)4 (0.71 g, 0.61 mmol, 0.03 eq.) and K2CO3 (8.5 g, 61.5 mmol, 3.0 eq.) in a degassed mixture of dioxane and water (3:1). The reaction mixture was stirred at reflux overnight. After cooling to room temperature, the reaction mixture was filtered through a pad of Florisil and the aqueous phase was separated. The organic phase was filtered again through Florisil, washed with CHCl3, and stirred in 3% NaDTC solution at room temperature. After removal of the aqueous phase, the organic solvent was filtered through silica gel and washed with MeOH. After precipitation with toluene, the product was finally purified by sublimation and 6.1 g (44%) of solid was isolated. HPLC / ESI-MS: 1277 [2M+H]+ .

[0486] Supporting materials for device experiments

[0487] C1 is CAS 2098308-14-4

[0488] C2 is CAS 2252183-63-2

[0489] C3 is CAS 2253724-56-8

[0490] A1 is CAS 2098710-88-2

[0491] F1 is CAS 1364603-07-5

[0492] F2 is CAS 1613079-70-1

[0493] F3 is CAS 2032364-64-8

[0494] F4 is CAS 1955543-57-3

[0495] F5 CAS 1242056-42-3

[0496] F6 CAS 721969-94-4

[0497] F7 CAS 2437303-42-7

[0498] F8 CAS 2032364-64-8

[0499] PD2 CAS 1224447-88-4

[0500] ND1 CAS 1440864-50-5

[0501] LiQ is 8-hydroxyquinolate lithium, CAS 850918-68-2.

[0502] H09 is the emitter host and BD200 is the blue fluorescent emitter dopant, both of which are commercially available from SFC in Korea.

[0503] Preparation of model blue OLED devices

[0504] The device is prepared by depositing a 10 nm hole injection layer of F1 (98:2 volume % by weight ratio of matrix to dopant) doped with PD2 on a glass substrate with a silver anode, and then depositing a 128 nm thick undoped hole transport layer of F1. A 5 nm electron blocking layer of F2 is deposited on the HTL. Subsequently, a blue fluorescent light-emitting layer of the luminous body H09 (Sun Fine Chemicals) (97:3 volume %) doped with BD200 (Sun Fine Chemicals) with a thickness of 20 nm is deposited. On the light-emitting layer, a 5 nm layer made of F3 is deposited as a hole blocking layer. A 31 nm thick electron transport layer made of the test compound and ND1 is co-deposited on the HBL at a volume ratio of 60:40. Subsequently, a 2 nm thick electron injection layer is deposited on the ETL, and then a 13 nm thick cathode composed of a silver-magnesium alloy with a volume ratio of 90:10 is deposited. Finally, a 75 nm thick capping layer made of F5 is deposited on top of the cathode. All depositions are completed by vacuum thermal evaporation.

[0505] Device Embodiment

[0506] 1) Blue fluorescent top-emitting OLED with EIL doped with Li salt

[0507] Table 1a schematically describes the model device.

[0508] Table 1a

[0509]

[0510] The results are shown in Table 1b.

[0511] Table 1b

[0512]

[0513] Compared to the prior art analogue A1 comprising a diisopropylphosphine oxide group, the diisobutylphosphine oxide compound E1 according to the invention exhibits a significantly improved lifetime.

[0514] 2) Blue fluorescent top-emitting OLED with hybrid organic ETL

[0515] The devices were prepared by a VTE process similar to the previously described devices, with the differences shown in Table 2a.

[0516] Table 2a

[0517]

[0518] The results are shown in Tables 2b and 2c.

[0519] Table 2b

[0520]

[0521] Compared to the prior art analogue A1 comprising a diisopropylphosphine oxide group, the dineopentylphosphine oxide compound E3 according to the invention exhibits an increased efficiency.

[0522] Table 2c

[0523]

[0524] Compared to analogs A2 comprising a diethylphosphine oxide group and A3 comprising a diisopropylphosphine oxide group, the diisobutylphosphine oxide compound E2 according to the invention exhibits improved efficiency and voltage.

[0525] 3) Blue fluorescent top-emitting OLED with hybrid organic ETL

[0526] The devices were prepared by a VTE process similar to the previously described devices, with the differences shown in Table 3a.

[0527] Table 3a

[0528]

[0529] The results are shown in Tables 3b and 3c.

[0530] Table 3b

[0531]

[0532] Compared to the prior art analogue A1 comprising a diisopropylphosphine oxide group, the dineopentylphosphine oxide compound E3 according to the invention exhibits an increased efficiency.

[0533] Table 3c

[0534]

[0535] Compared to analogs A2 comprising a diethylphosphine oxide group and A3 comprising a diisopropylphosphine oxide group, the diisobutylphosphine oxide compound E2 according to the invention exhibits improved efficiency and voltage.

[0536] 4) Blue fluorescent top-emitting OLED with pure organic ETL

[0537] The devices were prepared by a VTE process similar to the previously described devices, with the differences shown in Table 4a.

[0538] Table 4a

[0539]

[0540] The results are shown in Table 4b.

[0541] Table 4b:

[0542]

[0543] Compared with the dimethylphosphine oxide compound C3, the dineopentylphosphine oxide compounds E19 and E4 of the present invention and the diisobutylphosphine oxide compound E2 of the present invention exhibit improved operating voltage and current efficiency.

[0544] 5) Blue fluorescent top-emitting OLED with pure organic ETL

[0545] The devices were prepared by a VTE process similar to the previously described devices, with the differences shown in Table 5a.

[0546] Table 5a

[0547]

[0548] The results are shown in Table 5b.

[0549] Table 5b:

[0550]

[0551] Compared with the dimethylphosphine oxide compound C3, the dineopentylphosphine oxide compounds E19 and E4 of the present invention and the diisobutylphosphine oxide compound E2 of the present invention exhibit improved operating voltage and current efficiency.

[0552] 6) Blue fluorescent top-emitting OLED with pure organic ETL

[0553] The devices were prepared by a VTE process similar to the previously described devices, with the differences shown in Table 6a.

[0554] Table 6a

[0555]

[0556] The results are shown in 6b.

[0557] Table 6b:

[0558]

[0559] Compared with the dimethylphosphine oxide compound C3, the dineopentylphosphine oxide compounds E19 and E4 of the present invention and the diisobutylphosphine oxide compound E2 of the present invention exhibit improved operating voltage and current efficiency.

[0560] Adaptability of vacuum thermal evaporation manufacturing method

[0561] Advantageously for the production of organic semiconductor layers by vacuum thermal evaporation, the dineopentylphosphine oxide compounds of the invention exhibit a combination of high thermal stability and good volatility.

[0562] Table 7 shows that, although the molar masses of the dineopentylphosphine oxide compounds are significantly higher than those of their dimethylphosphine oxide analogs, the volatility of the compounds E3, E4 and E19 of the present invention is slightly higher than that of the corresponding dimethylphosphine analogs C1, C2 and C3 in terms of their standard onset vaporization temperature and the temperature of 50% weight loss in a standard high vacuum TGA test:

[0563] Table 7

[0564]

[0565] In terms of thermal stability to the onset of decomposition in standard TGA-DSC testing, compounds E3, E4 and E19 of the present invention and their dimethylphosphine oxide analogs C1, C2 and C3 showed no signs of decomposition at temperatures up to 415°C.

[0566] The technical features disclosed in the foregoing description and the dependent claims can serve as materials for realizing aspects of the inventive contents disclosed in the independent claims in their various forms, both individually and in any combination thereof.

Claims

1. A semiconductor material, comprising a first organic compound, wherein the first organic compound comprises: - at least one charge transporting moiety comprising at least one aromatic ring; and - at least one group represented by the following formula (1): (1) in - Wavy Line" " represents the position at which the group represented by formula (1) is bonded to the remaining structure of the first organic compound; and -R 1 and R 2 Independently selected from H and CH3.

2. The semiconductor material according to claim 1, wherein the charge transport moieties are independently selected from: - heteroaromatic moieties containing at least two heteroatoms; - an aryl group comprising at least two fused aromatic rings; and - a heteroaryl group comprising at least two fused aromatic rings.

3. The semiconductor material of claim 1 or 2, wherein the aromatic heterocyclic moiety comprising at least two heteroatoms is independently selected from diazine, triazine, quinazoline, quinoxaline, benzoquinazoline, benzoquinoxaline, azacarbazole, azadibenzofuran, azadibenzothiophene, naphthyridine, benzimidazole, benzothiazole, benzoimidazolyl, imidazopyridine and imidazopyrimidine.

4. The semiconductor material according to claim 2 or 3, wherein the aryl group comprising at least two fused aromatic rings is independently selected from anthracene, phenanthrene and pyrene.

5. The semiconductor material according to any one of claims 2 to 4, wherein the heteroaryl group comprising at least two fused aromatic rings is independently selected from azaanthracene, azaphenanthracene, diazaanthracene, diazaphenanthracene, benzoacridine and dibenzoacridine.

6. A semiconductor material according to any one of the preceding claims, wherein R 1 and R 2 Select Same.

7. The semiconductor material according to any one of the preceding claims, wherein the first organic compound is represented by the following formula (2): (2) in R 1 and R 2 Independently selected from H and CH3; A is the charge transport structure; and L is a direct bond or a spacer.

8. The semiconductor material according to claim 7, wherein L is selected from an aromatic subunit and a heteroaromatic subunit.

9. The semiconductor material according to claim 7 or 8, wherein L is selected from a phenylene group and a 1,1'-biphenyl-diyl group.

10. A semiconductor material according to any preceding claim, wherein the semiconductor material further comprises an n-type electron dopant.

11. A method for preparing a layer of semiconductor material according to any one of the preceding claims, comprising the step of depositing the first organic compound on a solid support.

12. An organic semiconductor device comprising at least one layer comprising the semiconductor material according to any one of claims 1 to 11. 13 . The organic semiconductor device according to claim 12 , wherein the layer comprising a semiconductor material is an electron transport layer, an electron injection layer or an electron generation layer. 14 . The organic semiconductor device according to claim 12 , wherein the organic semiconductor device is an organic diode, an organic transistor, an organic solar cell or an organic light emitting diode.

15. A compound comprising: - at least one charge transporting moiety comprising at least one aromatic ring, wherein said charge transporting moieties are independently selected from: - a heteroaromatic moiety comprising at least two heteroatoms; - an aryl group comprising at least three fused aromatic rings; and - a heteroaryl group comprising at least three fused aromatic rings; and - at least one group represented by the following formula (1): (1) in - Wavy Line" " represents the position at which the group represented by formula (1) is bonded to the remaining structure of the first organic compound; and -R 1 and R 2 Independently selected from H and CH3.

16. A compound comprising: - at least one charge transporting moiety comprising at least one aromatic ring, wherein said charge transporting moieties are independently selected from: - a heteroaromatic moiety comprising at least two heteroatoms; - an aryl group comprising at least two fused aromatic rings; and - a heteroaryl group comprising at least two fused aromatic rings; and - at least one group represented by the following formula (1): (1b) in - Wavy Line" " represents the position where the group represented by formula (I) is bonded to the remaining structure of the first organic compound, -R 1 and R 2 are independently selected from H and CH3, and -R 1 and R 2 At least one of them is CH3.

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