Compound, semiconductor material, organic electronic device, display device, and method for manufacturing same

Abstract

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

Description

Technical Field

[0001] The present invention relates to a compound. The present invention also relates to a semiconductor material comprising the compound, an organic electronic device comprising the semiconductor material, a display device comprising the organic electronic device, and a method for manufacturing the organic electronic device. Background Art

[0002] As an organic semiconductor device as a self-luminous device, such as an organic light emitting diode OLED, has a wide viewing angle, excellent contrast ratio, fast response, high brightness, excellent operating voltage characteristics, and color reproduction. A typical OLED includes an anode, a hole transport layer HTL, a light emitting layer EML, an electron transport layer ETL, and a cathode, which are sequentially stacked on a substrate. In this regard, the HTL, EML, and ETL are thin films formed of an organic compound.

[0003] When a voltage is applied to the anode and the cathode, holes injected from the anode move through the HTL to the EML, and electrons injected from the cathode move through the ETL to the EML. The holes and electrons recombine in the EML to generate excitons. When the excitons drop from the excited state to the 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 long lifetime.

[0004] The performance of an organic light emitting diode can be affected by the characteristics of the organic semiconductor layer, and among them, can be affected by the characteristics of the organic material of the organic semiconductor layer.

[0005] Specifically, it is necessary to develop an organic semiconductor layer capable of increasing the electron mobility and at the same time increasing the electrochemical stability, so that an organic semiconductor device such as an organic light emitting diode can be applied to a large flat panel display.

[0006] In addition, it is necessary to develop an organic semiconductor layer capable of having an extended lifetime at a higher current density and thus at a higher brightness. In particular, it is necessary to develop an organic semiconductor material or a semiconductor layer to reduce the operating voltage, which is important for reducing the power consumption of, for example, a mobile display device and increasing the battery life.

[0007] Therefore, an object of the present invention is to provide a compound and a semiconductor material for manufacturing an organic electronic device, and a display device that overcomes the defects of the prior art, particularly having improved performance, especially having improved lifetime and current efficiency. Summary of the Invention

[0008] This object is achieved by a compound of formula (I):

[0009] (I),

[0010] wherein

[0011] - A, A', and A" are independently selected from substituted or unsubstituted C1 to C 20 alkyl, substituted or unsubstituted C1 to C 20 alkenyl, substituted or unsubstituted C6 to C 60 aryl, and substituted or unsubstituted C2 to C 60 heteroaryl;

[0012] - L and L" are independently selected from substituted or unsubstituted C6 to C 60 aryl and substituted or unsubstituted C2 to C 60 heteroaryl, and L' is selected from H, D, C1 to C 20 alkyl, substituted or unsubstituted C1 to C 20 alkenyl, substituted or unsubstituted C6 to C 60 aryl, and substituted or unsubstituted C2 to C 60 heteroaryl;

[0013] Or

[0014] - L is selected from substituted or unsubstituted C6 to C 60 aryl and substituted and unsubstituted C2 to C 60 heteroaryl, and L' and L" together form a fused 6-membered aromatic ring,

[0015] wherein the fused 6-membered aromatic ring

[0016] - is unsubstituted,

[0017] Or

[0018] - is substituted with one or more substituents independently selected from (substituted or unsubstituted) C6 to C 56 aryl, provided that the total number of C atoms in all substituents does not exceed 56,

[0019] Or

[0020] - is fused to a second 6-membered aromatic ring, wherein the fused 6-membered aromatic ring and the second 6-membered aromatic ring are unsubstituted, or at least one of the fused 6-membered aromatic ring and the second 6-membered aromatic ring is substituted with one or more substituents independently selected from (substituted or unsubstituted) C6 to C 40 aryl, provided that the total number of C atoms in all substituents does not exceed 40;

[0021] - E is independently selected from H, D, halogen, SiR a R b R c (wherein R a 、R b and R cindependently selected from C1-C6 alkyl and phenyl), C1-C6 alkyl, C1-C6 alkoxy, CN and P(=O)R d R e (wherein R d and R e are independently selected from C1-C6 alkyl and phenyl);

[0022] - G is independently selected from H, D, halogen, SiR a R b R c (wherein R a 、R b and R c are independently selected from C1-C6 alkyl and phenyl), C1-C6 alkyl, C1-C6 alkoxy, CN and P(=O)R d R e (wherein R d and R e are independently selected from C1-C6 alkyl and phenyl).

[0023] This object is also achieved by a semiconductor material comprising a compound of formula (I) according to the invention.

[0024] This object is also achieved by an organic electronic device comprising a semiconductor layer, wherein the semiconductor layer comprises a semiconductor material according to the invention.

[0025] This object is also achieved by a display device comprising an organic electronic device according to the invention.

[0026] This object is also achieved by a method for preparing an organic electronic device according to the invention, wherein the method comprises the step of depositing a compound according to the invention on a solid support.

[0027] Surprisingly, it has been found that the compounds according to the invention and the semiconductor materials comprising said compounds can each be used to prepare organic electronic devices and display devices having improved properties, in particular improved lifetime and current efficiency, compared to the corresponding devices of the prior art.

[0028] Compound

[0029] According to one aspect, the invention relates to a compound of formula (I):

[0030] (I).

[0031] Unless otherwise explicitly mentioned, all compounds, groups, moieties, substituents, etc. shown herein, in particular by structural formulas, by systematic names, etc., encompass their corresponding partially deuterated and fully deuterated derivatives.

[0032] According to the present disclosure, in the formula showing the following combination cases,

[0033]

[0034] the group R can be bonded to any suitable bonding position.

[0035] For example, a biphenylylene spacer

[0036]

[0037] can be 1,1'-biphenyl-4,4'-diyl, 1,1'-biphenyl-3,4'-diyl, 1,1'-biphenyl-2,4'-diyl, 1,1'-biphenyl-3,3'-diyl, 1,1'-biphenyl-2,3'-diyl, 1,1'-biphenyl-2,2'-diyl.

[0038] In a specific embodiment, the biphenylylene spacer can have one of the following structures:

[0039] ; ;

[0040] ; ;

[0041] wherein the biphenylylene spacer is bonded to at

[0042] by a bond,

[0043] and the biphenylylene spacer is bonded to at

[0044] by a bond;

[0045] and E and G are independently selected from H, D, halogen, SiR a R b R c (wherein R a , R b and R c are independently selected from C1 to C6 alkyl and phenyl), C1 to C6 alkyl, C1 to C6 alkoxy, CN and P(=O)R d R e (wherein R d and R e are independently selected from C1 to C6 alkyl and phenyl).

[0046] A, A' and A" are independently selected from substituted or unsubstituted C1 to C 20Alkyl, substituted or unsubstituted C1 to C 20 Alkenyl, substituted or unsubstituted C6 to C 60 Aryl and substituted or unsubstituted C2 to C 60 Heteroaryl.

[0047] One or more substituents on A, A' and A" are independently selected from D, halogen, SiR a R b R c (wherein R a 、R b and R c are independently selected from C1 to C6 alkyl and phenyl), C1 to C6 alkyl, C1 to C6 alkoxy, CN and P(=O)R d R e (wherein R d and R e are independently selected from C1 to C6 alkyl and phenyl).

[0048] A, A' and A" can independently be selected from substituted or unsubstituted C1 to C 12 alkyl, substituted or unsubstituted C1 to C 12 alkenyl, substituted or unsubstituted C6 to C 48 aryl and substituted or unsubstituted C2 to C 47 heteroaryl. A, A' and A" can independently be selected from substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkenyl, substituted or unsubstituted C6 to C 36 aryl and substituted or unsubstituted C2 to C 36 heteroaryl. A, A' and A" can independently be selected from substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted C1 to C4 alkenyl, substituted or unsubstituted C6 to C 18 aryl and substituted or unsubstituted C2 to C 18 heteroaryl. A, A' and A" can independently be selected from substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted C1 to C4 alkenyl, substituted or unsubstituted phenyl and substituted or unsubstituted C2 to C5 heteroaryl.

[0049] A, A' and A" can independently be selected from substituted or unsubstituted C6 to C 60 aryl and substituted or unsubstituted C2 to C 60 heteroaryl. A, A' and A" can independently be selected from substituted or unsubstituted C6 to C 48 aryl and substituted or unsubstituted C2 to C 47 heteroaryl. A, A' and A" can independently be selected from substituted or unsubstituted C6 to C 36 aryl and substituted or unsubstituted C2 to C36 Heteroaryl. A, A', and A" can each independently be selected from substituted or unsubstituted C6 to C 18 aryl and substituted or unsubstituted C2 to C 18 heteroaryl. A, A', and A" can each independently be selected from substituted or unsubstituted phenyl and substituted or unsubstituted C2 to C5 heteroaryl.

[0050] A, A', and A" can each independently be selected from substituted or unsubstituted C6 to C 60 aryl. A, A', and A" can each independently be selected from substituted or unsubstituted C6 to C 48 aryl. A, A', and A" can each independently be selected from substituted or unsubstituted C6 to C 36 aryl. A, A', and A" can each independently be selected from substituted or unsubstituted C6 to C 18 aryl. A, A', and A" can each independently be selected from substituted or unsubstituted phenyl. A, A', and A" can each be unsubstituted phenyl.

[0051] In a first alternative, L and L" are each independently selected from substituted or unsubstituted C6 to C 60 aryl and substituted or unsubstituted C2 to C 60 heteroaryl, and L' is selected from H, D, C1 to C 20 alkyl, substituted or unsubstituted C1 to C 20 alkenyl, substituted or unsubstituted C6 to C 60 aryl and substituted or unsubstituted C2 to C 60 heteroaryl.

[0052] In the case where the respective groups are substituted, one or more substituents on L, L', and L" are each independently selected from D, halogen, SiR a R b R c (wherein R a 、R b and R c are each independently selected from C1 to C6 alkyl and phenyl), C1 to C6 alkyl, C1 to C6 alkoxy, CN, and P(=O)R d R e (wherein R d and R e are each independently selected from C1 to C6 alkyl and phenyl).

[0053] In this first alternative, L and L" can each independently be selected from substituted or unsubstituted C6 to C 48 aryl and substituted or unsubstituted C2 to C 47 heteroaryl, and L' can be selected from H, D, C1 to C 12 alkyl, substituted or unsubstituted C1 to C12 Alkenyl, substituted or unsubstituted C6 to C 48 Aryl and substituted or unsubstituted C2 to C 47 Heteroaryl. In this first alternative, L and L" can independently be selected from substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C2 to C 35 Heteroaryl, and L' can be selected from H, D, C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkenyl, substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C2 to C 35 Heteroaryl. In this first alternative, L and L" can independently be selected from substituted or unsubstituted C6 to C 18 Aryl and substituted or unsubstituted C2 to C 17 Heteroaryl, and L' can be selected from H, D, C1 to C4 alkyl, substituted or unsubstituted C1 to C4 alkenyl, substituted or unsubstituted C6 to C 18 Aryl and substituted or unsubstituted C2 to C 17 Heteroaryl. In this first alternative, L and L" can independently be selected from substituted or unsubstituted phenyl and substituted or unsubstituted C2 to C5 heteroaryl, and L' can be selected from H, D, C1 to C4 alkyl, substituted or unsubstituted C1 to C4 alkenyl, substituted or unsubstituted phenyl and substituted or unsubstituted C2 to C5 heteroaryl.

[0054] In this first alternative, L and L" can independently be selected from substituted or unsubstituted C6 to C 48 Aryl and substituted or unsubstituted C2 to C 47 Heteroaryl, and L' can be selected from H, D, C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkenyl. In this first alternative, L and L" can independently be selected from substituted or unsubstituted C6 to C 36 Aryl and substituted or unsubstituted C2 to C 35 Heteroaryl, and L' can be selected from H, D, C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkenyl. In this first alternative, L and L" can independently be selected from substituted or unsubstituted C6 to C 18 Aryl and substituted or unsubstituted C2 to C 17 Heteroaryl, and L' can be selected from H, D, C1 to C4 alkyl, substituted or unsubstituted C1 to C4 alkenyl. In this first alternative, L and L" can independently be selected from substituted or unsubstituted phenyl and substituted or unsubstituted C2 to C5 heteroaryl, and L' can be selected from H, D, C1 to C4 alkyl, substituted or unsubstituted C1 to C4 alkenyl.

[0055] In this first alternative, L and L" can independently be selected from substituted or unsubstituted C6 to C 48 aryl, and L' can be selected from H and D. In this first alternative, L and L" can independently be selected from substituted or unsubstituted C6 to C 36 aryl, and L' can be selected from H and D. In this first alternative, L and L" can independently be selected from substituted or unsubstituted C6 to C 18 aryl, and L' can be selected from H and D. In this first alternative, L and L" can independently be selected from substituted or unsubstituted phenyl, and L' can be selected from H and D. In this first alternative, L and L" can independently be selected from substituted or unsubstituted C6 to C 60 aryl, and L' can be H. In this first alternative, L and L" can each be unsubstituted phenyl, and L' can be H.

[0056] In a second alternative, L is selected from substituted or unsubstituted C6 to C 60 aryl and substituted or unsubstituted C2 to C 60 heteroaryl, and L' and L" together form a fused 6-membered aromatic ring,

[0057] wherein the fused 6-membered aromatic ring

[0058] - is unsubstituted,

[0059] or

[0060] - is substituted with one or more substituents independently selected from substituted or unsubstituted C6 to C 56 aryl, provided that the total number of C atoms in all substituents does not exceed 56, wherein the C6 to C 56 aryl substituent may further be substituted with one or more substituents selected from D, halogen, SiR a R b R c (wherein R a 、R b and R c are independently selected from C1 to C6 alkyl and phenyl), C1 to C6 alkyl, C1 to C6 alkoxy, CN, and P(=O)R d R e (wherein R d and R e are independently selected from C1 to C6 alkyl and phenyl),

[0061] or

[0062] - Condensed with a second 6-membered aromatic ring, wherein the condensed 6-membered aromatic ring and the second 6-membered aromatic ring are unsubstituted, or at least one of the condensed 6-membered aromatic ring and the second 6-membered aromatic ring is substituted with one or more substituents independently selected from C6 to C 40 aryl, provided that the total number of C atoms in all substituents does not exceed 40, wherein the C6 to C 40 aryl substituent may further be substituted with one or more substituents selected from D, halogen, SiR a R b R c (wherein R a 、R b and R c are independently selected from C1 to C6 alkyl and phenyl), C1 to C6 alkyl, C1 to C6 alkoxy, CN, and P(=O)R d R e (wherein R d and R e are independently selected from C1 to C6 alkyl and phenyl).

[0063] For example, in the case where L' and L" together form an unsubstituted condensed 6-membered aromatic ring, the following structure is formed:

[0064] ,

[0065] where the attachment to the rest of the structure of formula (I) is at .

[0066] For example, in the case where L' and L" together form a condensed 6-membered aromatic ring condensed with a second 6-membered aromatic ring, wherein the condensed 6-membered aromatic ring and the second 6-membered aromatic ring are unsubstituted, the following structure can be formed:

[0067] ,

[0068] where the attachment to the rest of the structure of formula (I) is at .

[0069] In the case where the corresponding groups are substituted, one or more substituents on L, L', and L" are independently selected from D, halogen, SiR a R b R c (wherein R a 、R b and R c are independently selected from C1 to C6 alkyl and phenyl), C1 to C6 alkyl, C1 to C6 alkoxy, CN, and P(=O)R d R e (wherein R d and R eindependently selected from C1 to C6 alkyl and phenyl). This includes substituents on the aryl substituent attached to L 1 and L 2 connected.

[0070] In this second alternative, L may be selected from substituted or unsubstituted C6 to C 48 aryl and substituted or unsubstituted C2 to C 47 heteroaryl, and L' and L" may together form a fused 6-membered aromatic ring,

[0071] wherein the fused 6-membered aromatic ring

[0072] - is unsubstituted,

[0073] or

[0074] - is substituted with one or more substituents independently selected from substituted or unsubstituted C6 to C 44 aryl, provided that the total number of C atoms in all substituents does not exceed 44,

[0075] or

[0076] - is fused to a second 6-membered aromatic ring, wherein the fused 6-membered aromatic ring and the second 6-membered aromatic ring are unsubstituted, or at least one of the fused 6-membered aromatic ring and the second 6-membered aromatic ring is substituted with one or more substituents independently selected from substituted or unsubstituted C6 to C 28 aryl, provided that the total number of C atoms in all substituents does not exceed 28.

[0077] In this second alternative, L may be selected from substituted or unsubstituted C6 to C 18 aryl and substituted or unsubstituted C2 to C 47 heteroaryl, and L' and L" may together form a fused 6-membered aromatic ring,

[0078] wherein the fused 6-membered aromatic ring

[0079] - is unsubstituted,

[0080] or

[0081] - is substituted with one or more substituents independently selected from substituted or unsubstituted C6 to C 14 aryl, provided that the total number of C atoms in all substituents does not exceed 14,

[0082] or

[0083] - Condensed with a second 6-membered aromatic ring, wherein the condensed 6-membered aromatic ring and the second 6-membered aromatic ring are unsubstituted, or at least one of the condensed 6-membered aromatic ring and the second 6-membered aromatic ring is substituted with one or more substituents independently selected from substituted or unsubstituted C6 to C 12 aryl, provided that the total number of C atoms in all substituents does not exceed 12.

[0084] In this second alternative, L may be selected from substituted or unsubstituted C6 to C 60 aryl, and L' and L" may together form a condensed 6-membered aromatic ring,

[0085] wherein the condensed 6-membered aromatic ring

[0086] - is unsubstituted,

[0087] or

[0088] - is substituted with one or more substituents independently selected from substituted or unsubstituted C6 to C 56 aryl, provided that the total number of C atoms in all substituents does not exceed 56.

[0089] In this second alternative, L may be selected from substituted or unsubstituted phenyl and substituted or unsubstituted C2 to C5 heteroaryl, and L' and L" together form a condensed 6-membered aromatic ring,

[0090] wherein the condensed 6-membered aromatic ring

[0091] - is unsubstituted,

[0092] or

[0093] - is condensed with a second 6-membered aromatic ring, wherein the condensed 6-membered aromatic ring and the second 6-membered aromatic ring are unsubstituted.

[0094] In this second alternative, L may be phenyl, and L' and L" together form a condensed 6-membered aromatic ring,

[0095] wherein the condensed 6-membered aromatic ring

[0096] - is unsubstituted,

[0097] or

[0098] - is condensed with a second 6-membered aromatic ring, wherein the condensed 6-membered aromatic ring and the second 6-membered aromatic ring are unsubstituted.

[0099] E is independently selected from H, D, halogen, SiR a R b R c (wherein R a 、R band R c are independently selected from C1-C6 alkyl and phenyl), C1-C6 alkyl, C1-C6 alkoxy, CN and P(=O)R d R e (wherein R d and R e are independently selected from C1-C6 alkyl and phenyl).

[0100] E can be independently selected from H, D, C1-C6 alkyl and C1-C6 alkoxy. E can be independently selected from H, D and C1-C6 alkyl. E can be independently selected from H and D. Each E can be H.

[0101] G is independently selected from H, D, halogen, SiR a R b R c (wherein R a , R b and R c are independently selected from C1-C6 alkyl and phenyl), C1-C6 alkyl, C1-C6 alkoxy, CN and P(=O)R d R e (wherein R d and R e are independently selected from C1-C6 alkyl and phenyl).

[0102] G can be independently selected from H, D, C1-C6 alkyl and C1-C6 alkoxy. G can be independently selected from H, D and C1-C6 alkyl. G can be independently selected from H and D. Each G can be H.

[0103] According to one embodiment, the present invention relates to a compound of formula (I):

[0104] (I),

[0105] wherein

[0106] - A, A' and A" are independently selected from substituted or unsubstituted C6-C 60 aryl;

[0107] - L and L" are independently selected from substituted or unsubstituted C6-C 48 aryl, and L' is selected from H and D;

[0108] or

[0109] - L is selected from substituted or unsubstituted C6-C 60 aryl, and L' and L" together form a fused 6-membered aromatic ring,

[0110] wherein the fused 6-membered aromatic ring

[0111] - unsubstituted,

[0112] or

[0113] - fused to a second 6-membered aromatic ring, wherein the fused 6-membered aromatic ring and the second 6-membered aromatic ring are substituted or unsubstituted;

[0114] - E is independently selected from H, D, C1-C6 alkyl, and C1-C6 alkoxy;

[0115] - G is independently selected from H, D, C1-C6 alkyl, and C1-C6 alkoxy.

[0116] According to one embodiment, the present invention relates to a compound of formula (I):

[0117] (I),

[0118] wherein

[0119] - A, A', and A" are each unsubstituted phenyl;

[0120] - L and L" are each unsubstituted phenyl, and L' is H;

[0121] or

[0122] - L is unsubstituted phenyl, and L' and L" together form a fused 6-membered aromatic ring,

[0123] wherein the fused 6-membered aromatic ring

[0124] - is unsubstituted,

[0125] or

[0126] - is fused to a second 6-membered aromatic ring, wherein the fused 6-membered aromatic ring and the second 6-membered aromatic ring are unsubstituted;

[0127] - E is each H;

[0128] - G is each H.

[0129] The compound of formula (I) may be selected from the following compounds E1 to E7.

[0130] E1 E2

[0131] E3 E4

[0132] E5 E6

[0133] E7。

[0134] Semiconductor material

[0135] According to one aspect, the present invention relates to a semiconductor material comprising a compound of formula (I) according to the present invention as defined herein.

[0136] The semiconductor material may be an organic semiconductor material. The semiconductor material may be an electron transport material.

[0137] Relative to the total weight of the semiconductor material, the semiconductor material may comprise at least 50% by weight of the compound of formula (I). Relative to the total weight of the semiconductor material, the semiconductor material may comprise at least 60% by weight of the compound of formula (I). Relative to the total weight of the semiconductor material, the semiconductor material may comprise at least 70% by weight of the compound of formula (I). Relative to the total weight of the semiconductor material, the semiconductor material may comprise at least 80% by weight of the compound of formula (I). Relative to the total weight of the semiconductor material, the semiconductor material may comprise at least 90% by weight of the compound of formula (I). Relative to the total weight of the semiconductor material, the semiconductor material may comprise at least 95% by weight of the compound of formula (I). Relative to the total weight of the semiconductor material, the semiconductor material may comprise at least 98% by weight of the compound of formula (I). Relative to the total weight of the semiconductor material, the semiconductor material may comprise at least 99% by weight of the compound of formula (I). The semiconductor material may consist essentially of the compound of formula (I). The semiconductor material may consist of the compound of formula (I).

[0138] The semiconductor material may be undoped. Alternatively, the semiconductor material may be doped with an n-type electrical dopant.

[0139] An n-type dopant is understood to be a compound which, when incorporated into an electron transport matrix material, improves the electronic properties (especially in terms of electron injection and / or electron conductivity) of the resulting semiconductor material compared to the pure electron transport matrix material under the same physical conditions.

[0140] In the context of the present invention, "incorporated into an electron transport matrix" means homogeneous mixing with the electron transport matrix.

[0141] The n-type dopant may be selected from elemental metals, metal salts, metal complexes and organic groups.

[0142] The metal salt may be selected from alkali metal salts and alkaline earth metal salts, and in one embodiment, is selected from Li, Na, K, R, Cs, Mg, Ca, Sr, and Ba salts. The salt may comprise an anion selected from halogen anions, complex borate anions, and organic phenolate anions. In one embodiment, the anion in the salt may be a cation chelating anion, such as 8-hydroxyquinoline anion and / or 2-phosphonyl-phenolate anion.

[0143] 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; even more preferably selected from lithium fluoride, lithium quinolate, lithium borate, lithium phenolate, lithium pyridinolate, or lithium complexes with Schiff base ligands; most preferably,

[0144] - The lithium complex has formula II, formula III, or formula IV:

[0145] ,

[0146] where

[0147] A1 to A6 are the same or independently selected from CH, CR, N, O;

[0148] R is the same or independently selected from hydrogen, halogen, an alkyl group, an aryl group, or a heteroaryl group having 1 to 20 carbon atoms; more preferably, A1 to A6 are CH,

[0149] - The borate anion-based organic ligand is tetrakis(1H-pyrazol-1-yl)borate anion,

[0150] - The phenolate anion is 2-(pyridin-2-yl)phenolate anion, 2-phosphonyl-phenolate anion, such as 2-(diphenylphosphonyl)phenolate anion, imidazolophenolate anion, 2-(pyridin-2-yl)phenolate anion, or 2-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenolate anion,

[0151] - The pyridinolate anion is 2-(diphenylphosphonyl)pyridin-3-olate anion,

[0152] - The lithium Schiff base has structure 100, 101, 102, or 103:

[0153] .

[0154] According to one embodiment of the present invention, the semiconductor material of the present invention comprises a lithium organic complex or 8-hydroxyquinoline-lithium (=LiQ).

[0155] Organic electronic device

[0156] According to one aspect, the present invention relates to an organic electronic device, such as an organic semiconductor device, the organic electronic device comprising a semiconductor layer, the semiconductor layer comprising a semiconductor material according to the present invention. The semiconductor layer may consist of a semiconductor material according to the present invention.

[0157] The semiconductor layer may be a hole blocking layer and / or an electron transport layer and / or an electron injection layer. The semiconductor layer may be a hole blocking layer.

[0158] The organic electronic device may further comprise an anode, a cathode, and a light-emitting layer, wherein the light-emitting layer is disposed between the anode and the cathode, and the semiconductor layer is disposed between the light-emitting layer and the cathode.

[0159] The organic electronic device may further comprise an anode, a cathode, a light-emitting layer, and an electron transport layer, wherein the light-emitting layer and the electron transport layer are disposed between the anode and the cathode, and the semiconductor layer is disposed between the light-emitting layer and the electron transport layer.

[0160] The organic electronic device may further comprise an anode, a cathode, a light-emitting layer, and an electron transport layer, wherein the light-emitting layer and the electron transport layer are disposed between the anode and the cathode, and the semiconductor layer is disposed between the light-emitting layer and the electron transport layer, wherein the semiconductor layer is in direct contact with the light-emitting layer and / or the electron transport layer, preferably in direct contact with the light-emitting layer and / or the electron transport layer.

[0161] The organic electronic device may further comprise an anode, a cathode, a light-emitting layer, an electron transport layer, and an electron injection layer, wherein the light-emitting layer, the electron transport layer, and the electron injection layer are disposed between the anode and the cathode, and the semiconductor layer is disposed between the light-emitting layer and the electron transport layer, wherein the semiconductor layer is in direct contact with the light-emitting layer and / or the electron transport layer, preferably in direct contact with the light-emitting layer and / or the electron transport layer.

[0162] The organic electronic device may be an organic light-emitting diode.

[0163] In addition to a semiconductor layer comprising or consisting of a semiconductor material according to the present invention, the organic electronic device according to the present invention may in particular further comprise other layers. Exemplary embodiments of the corresponding layers are described below:

[0164] Substrate

[0165] The substrate can be any substrate commonly used in manufacturing 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.

[0166] Anode electrode

[0167] 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 for forming the anode electrode can be a high work function material to facilitate hole injection. The anode material can also be selected from low work function materials (i.e., aluminum). The anode electrode can be a transparent or reflective electrode. Transparent conductive oxides such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), aluminum zinc oxide (AlZO), and zinc oxide (ZnO) can be used to form the anode electrode. The anode electrode can also be formed using a metal or a metal alloy, which is typically silver (Ag), gold (Au).

[0168] Hole injection layer

[0169] A hole injection layer (HIL) can be formed on the anode by vacuum deposition, spin coating, printing, casting, slot die coating, Langmuir-Blodgett (LB) deposition, etc. When forming the HIL by vacuum deposition, the deposition conditions can vary depending on the compound used to form the HIL and the desired structure and thermal properties of the HIL. However, generally, the conditions for vacuum deposition can include a deposition temperature of 100 °C to 500 °C, a pressure of 10 -8 torr to 10 -3 torr (1 torr is equal to 133.322 Pa), and a deposition rate of 0.1 nm / s to 10 nm / s.

[0170] When forming the HIL by spin coating or printing, the coating conditions can vary depending on the compound used to form the HIL and the desired structure and thermal properties of the HIL. For example, the coating conditions can 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, the heat treatment removes the solvent.

[0171] The HIL can be formed from any compound commonly used to form the HIL. Examples of compounds useful for forming 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).

[0172] The HIL can contain or consist of a p-type dopant, and the p-type dopant can be selected from tetrafluoro-tetracyanoquinodimethane (F4TCNQ), 2,2'-(perfluoronaphthalene-2,6-diyl)dipropanedinitrile, or 2,2',2"-(cyclopropane-1,2,3-triyl)tris(2-(p-cyanotetrafluorophenyl)acetonitrile), but is not limited thereto. The HIL can be selected from hole-transporting matrix compounds doped with a p-type dopant. Typical examples of known hole-transporting materials doped are: copper phthalocyanine (CuPc) with a HOMO energy level of about -5.2 eV, doped with tetrafluoro-tetracyanoquinodimethane (F4TCNQ) having a LUMO energy level of about -5.2 eV; zinc phthalocyanine (ZnPc) doped with F4TCNQ (HOMO = -5.2 eV); α-NPD (N,N'-bis(naphthalen-1-yl)-N,N'-bis(phenyl)benzidine) doped with F4TCNQ, α-NPD doped with 2,2'-(perfluoronaphthalene-2,6-diyl)dipropanedinitrile. The p-type dopant concentration can be selected from 1 wt% to 20 wt%, more preferably from 3 wt% to 10 wt%.

[0173] The thickness of the HIL can be in the range of about 1 nm to about 100 nm, such as about 1 nm to about 25 nm. When the thickness of the HIL is in this range, the HIL can have excellent hole injection characteristics and will not cause substantial damage to the driving voltage.

[0174] Hole transport layer

[0175] A 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 for deposition and coating can be similar to those for forming the HIL. However, the conditions for vacuum or solution deposition can vary depending on the compound used to form the HTL.

[0176] The HTL can be formed from any compound commonly used to form the HTL. For example, Yasuhiko Shirota and Hiroshi Kageyama, Chem. Rev. 2007, 107, 953-1010 disclose applicable compounds, which 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(naphthalen-1-yl)-N,N'-diphenylbenzidine (α-NPD); and triphenylamine-based compounds such as 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA). Among these compounds, TCTA can transport holes and inhibit exciton diffusion into the EML.

[0177] The thickness of the HTL can range from about 5 nm to about 250 nm, preferably from about 10 nm to about 200 nm, more preferably from about 20 nm to about 190 nm, more preferably from about 40 nm to about 180 nm, more preferably from about 60 nm to about 170 nm, more preferably from about 80 nm to about 160 nm, more preferably from about 100 nm to about 160 nm, more preferably from about 120 nm to about 140 nm. The preferred thickness of the HTL can be 170 nm to 200 nm.

[0178] When the thickness of the HTL is within this range, the HTL can have excellent hole transport properties and will not cause substantial damage to the driving voltage.

[0179] Electron blocking layer

[0180] The function of the electron blocking layer (EBL) is to prevent electrons from transferring from the light-emitting layer to the hole transport layer and thus confine the electrons in the light-emitting layer. Thereby, the efficiency, operating voltage, and / or lifetime are improved. Generally, the electron blocking layer contains a triarylamine compound. The LUMO energy level of the triarylamine compound can be closer to the vacuum energy level than the LUMO energy level of the hole transport layer. The HOMO energy level of the electron blocking layer can be farther from the vacuum energy level than the HOMO energy level of the hole transport layer. The thickness of the electron blocking layer can be selected between 2 nm and 20 nm.

[0181] If the electron blocking layer has a high triplet energy level, it can also be described as a triplet control layer.

[0182] If a phosphorescent green or blue light-emitting layer is used, the function of the triplet control layer is to reduce triplet quenching. Thus, a higher luminous efficiency of the phosphorescent light-emitting layer can be achieved. The triplet control layer is selected from triarylamine compounds having a triplet energy level higher than that of the phosphorescent emitter in the adjacent light-emitting layer. EP 2 722 908 A1 describes compounds suitable for the triplet control layer, especially triarylamine compounds.

[0183] Photoactive layer (PAL)

[0184] The photoactive layer converts current into photons or photons into current.

[0185] 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 for deposition and coating can be similar to those for forming the HIL. However, the conditions for deposition and coating can vary depending on the compound used to form the PAL.

[0186] The photoactive layer may not contain the compound of formula (1).

[0187] The photoactive layer can be a light-emitting layer or a light-absorbing layer.

[0188] Emitting layer (EML)

[0189] 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 by vacuum deposition or spin coating, the conditions for deposition and coating can be similar to those for forming the HIL. However, the conditions for deposition and coating can vary depending on the compound used to form the EML.

[0190] The emitting layer may not contain the compound of formula (1).

[0191] The corresponding emitting layer (EML) can be formed by a combination of a host and a luminescent dopant. Examples of the host are Alq3, 4,4'-N,N'-dicarbazole-biphenyl (CBP), poly(n-vinylcarbazole) (PVK), 9,10-bis(naphthalen-2-yl)anthracene (ADN), 4,4',4''-tris(carbazol-9-yl)-triphenylamine (TCTA), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBI), 3-tert-butyl-9,10-di-2-naphthylanthracene (TBADN), stilbenylarylene (DSA), zinc bis(2-(2-hydroxyphenyl)benzothiazole) (Zn(BTZ)2), the following EML3, the following compound 1, and the following compound 2.

[0192]

[0193] EML3

[0194]

[0195] ADN

[0196]

[0197] Compound 1

[0198]

[0199] Compound 2

[0200] The luminescent dopant can be a phosphorescent or fluorescent emitter. Phosphorescent emitters and emitters that emit light through the thermally activated delayed fluorescence (TADF) mechanism can be preferred because of their higher efficiency. The emitter can be a small molecule or a polymer.

[0201] Examples of red luminescent dopants are PtOEP, Ir(piq)3, and Btp2Ir(acac), but are not limited thereto. These compounds are phosphorescent emitters; however, fluorescent red luminescent dopants can also be used.

[0202]

[0203] Examples of phosphorescent green luminescent dopants are Ir(ppy)3 (ppy = phenylpyridine), Ir(ppy)2(acac), and Ir(mpyp)3 as shown below. Compound 3 is an example of a fluorescent green luminescent emitter, and the structure is shown below.

[0204]

[0205]

[0206] Compound 3

[0207] Examples of phosphorescent blue luminescent dopants are F2Irpic, (F2ppy)2Ir(tmd), and Ir(dfppz)3, and tribenzofluorene, and the structures are shown below. Examples of fluorescent blue luminescent dopants are 4,4'-bis(4-diphenylaminostyryl)biphenyl (DPAVBi), 2,5,8,11-tetra-tert-butylperylene (TBPe), and Compound 4 below.

[0208]

[0209] Relative to 100 parts by weight of the host, the amount of the luminescent dopant can range from about 0.01 parts by weight to about 50 parts by weight. Alternatively, the light-emitting layer can be composed of a light-emitting polymer. The thickness of the EML can be from about 10 nm to about 100 nm, such as from about 20 nm to about 60 nm. When the thickness of the EML is within this range, the EML can have excellent luminescence and will not cause substantial damage to the driving voltage.

[0210] Hole blocking layer (HBL)

[0211] 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.

[0212] The HBL can also be referred to as an auxiliary ETL or a-ETL.

[0213] When the HBL is formed by vacuum deposition or spin coating, the conditions for deposition and coating can be similar to those for forming the HIL. However, the conditions for deposition and coating can vary depending on the compound used to form the HBL. Any compound commonly used to form the HBL can be used. Examples of compounds for forming the HBL include oxadiazole derivatives, triazole derivatives, and phenanthroline derivatives.

[0214] The thickness of the HBL can range from about 5 nm to about 100 nm, such as from about 10 nm to about 30 nm. When the thickness of the HBL is within this range, the HBL can have excellent hole blocking performance and will not cause substantial damage to the driving voltage.

[0215] The hole blocking layer can be manufactured from the semiconductor material according to the present invention.

[0216] Electron transport layer (ETL)

[0217] The semiconductor device according to the present invention can include an electron transport layer (ETL).

[0218] According to various embodiments, the OLED can include an electron transport layer or a stack of electron transport layers, the stack of electron transport layers including at least one first electron transport layer and at least one second electron transport layer.

[0219] By appropriately adjusting the energy levels of specific ETL layers, the injection and transport of electrons can be controlled, and holes can be effectively blocked. Therefore, the OLED can have a long lifespan.

[0220] The electron transport layer can contain an ETM material including one or more electron transport compounds known in the art.

[0221] According to one embodiment, the electron transport layer contains an electron transport compound, wherein the electron transport compound contains 8 to 13 aromatic or heteroaromatic rings, optionally 8 to 11 aromatic or heteroaromatic rings, optionally 9 to 11 aromatic or heteroaromatic rings, optionally 9 aromatic or heteroaromatic rings, wherein one or more of the aromatic or heteroaromatic rings may be substituted with a C1-C4 alkyl group. In this regard, the aromatic or heteroaromatic rings are each a monocyclic aromatic ring, such as a 6-membered aromatic ring like phenyl, a 6-membered heteroaromatic ring like pyridyl, a 5-membered heteroaromatic ring like pyrrolyl, etc. In this regard, in a fused (hetero)aromatic ring system, each ring is regarded as a monocyclic ring. For example, naphthalene contains two aromatic rings.

[0222] The electron transport compound may contain at least one heteroaromatic ring, optionally 1 to 5 heteroaromatic rings, optionally 1 to 4 heteroaromatic rings, optionally 1 to 3 heteroaromatic rings, optionally 1 or 2 heteroaromatic rings.

[0223] The aromatic or heteroaromatic rings of the electron transport compound may be 6-membered rings.

[0224] The heteroaromatic rings of the electron transport compound may be N-containing heteroaromatic rings, optionally all heteroaromatic rings are N-containing heteroaromatic rings, and optionally all heteroaromatic rings contain N as the only type of heteroatom.

[0225] The electron transport compound may contain at least one six-membered heteroaromatic ring containing one to three N atoms in each heteroaromatic ring, optionally containing one to three 6-membered heteroaromatic rings each containing one to three N atoms in each heteroaromatic ring.

[0226] At least one 6-membered heteroaromatic ring contained in the electron transport compound may be an azine. At least one 6-membered heteroaromatic ring contained in the electron transport compound may be a triazine, diazine, pyrazine, pyrimidine, pyridine, quinazoline, or benzquinazoline, preferably a triazine.

[0227] If the electron transport compound contains two or more heteroaromatic rings, the heteroaromatic rings may be separated from each other by at least one aromatic ring without heteroatoms.

[0228] In one embodiment, the heteroatoms in the heteroaromatic rings of the electron transport compound are bonded to the molecular structure of the electron transport compound through at least one double bond.

[0229] In addition, the electron transport layer may comprise one or more additives. 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 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 an n-type dopant selected from Cs, K, Rb, Mg, Na, Ca, Sr, Eu, and Yb. In one embodiment, the alkali metal compound may be lithium 8-hydroxyquinoline (LiQ), lithium tetrakis(1H-pyrazol-1-yl)borate, or lithium 2-(diphenylphosphoryl)phenolate. There is no particular limitation on suitable compounds for the ETM (which can be used together with the compound of the present invention represented by the general formula (1) as defined above). In one embodiment, the electron transport matrix compound consists 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 included in an aromatic or heteroaromatic structural moiety, as disclosed, for example, in documents EP 1 970 371 A1 or WO 2013 / 079217 A1.

[0230] The electron transport layer may comprise a compound of formula (I) according to the present invention.

[0231] Electron injection layer (EIL)

[0232] An optional EIL that can facilitate electron injection from the cathode may be formed on the ETL, preferably directly on the electron transport layer. Examples of materials for forming the EIL include lithium 8-hydroxyquinoline (LiQ), LiF, NaCl, CsF, Li2O, BaO, Ca, Ba, Yb, 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 for forming the EIL.

[0233] 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 and will not cause substantial damage to the driving voltage.

[0234] The electron injection layer may comprise a compound of formula (I) according to the present invention.

[0235] Cathode electrode

[0236] Form a cathode electrode on the EIL (if present). The cathode electrode can be formed of a metal, an alloy, a conductive compound, or a mixture thereof. The cathode electrode can have a low work function. For example, the cathode electrode can be formed of lithium (Li), magnesium (Mg), aluminum (Al), aluminum (Al)-lithium (Li), calcium (Ca), barium (Ba), ytterbium (Yb), magnesium (Mg)-indium (In), magnesium (Mg)-silver (Ag), etc. Alternatively, the cathode electrode can be formed of a transparent conductive oxide such as ITO or IZO. The cathode can contain more than 50% by volume of a metal selected from Ag and Au.

[0237] The thickness of the cathode electrode can be in the range of about 5 nm to about 1000 nm, for example, in the range of about 10 nm to about 100 nm. When the thickness of the cathode electrode is in the range of about 5 nm to about 50 nm, the cathode electrode can be transparent or translucent even if it is formed of a metal or a metal alloy.

[0238] The cathode can be a translucent metal cathode with a thickness less than 20 nm, preferably less than 15 nm, and even more preferably less than 12 nm.

[0239] It should be understood that the cathode electrode is not part of the electron injection layer or the electron transport layer.

[0240] Charge generation layer / hole generation layer

[0241] The charge generation layer (CGL) consists of a bilayer.

[0242] The charge generation layer is a pn junction connecting an n-type charge generation layer (electron generation layer) and a p-type charge generation layer (hole generation layer). The n side of the pn junction generates electrons and injects them into the layer adjacent in the direction of the anode. Similarly, the p side of the pn junction generates holes and injects them into the layer adjacent in the direction of the cathode.

[0243] The charge generation layer is used in tandem devices, for example, in a tandem OLED that includes two or more light-emitting layers between two electrodes. In a tandem OLED that includes two light-emitting layers, the n-type charge generation layer provides electrons for the first light-emitting layer disposed near the anode, while the p-type charge generation layer provides holes for the second light-emitting layer disposed between the first light-emitting layer and the cathode.

[0244] The hole generation layer may be composed of an organic matrix material doped with a p-type dopant. Suitable matrix materials for the hole generation layer may be materials conventionally used as hole injection and / or hole transport matrix materials. Additionally, conventional materials may be used as the p-type dopant for the hole generation layer. For example, the p-type dopant may be one selected from tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), tetracyanoquinodimethane derivatives, annulene derivatives, iodine, FeCl3, FeF3, and SbCl5. Further, the host may be one selected from N,N'-bis(naphthalen-1-yl)-N,N-diphenyl-benzidine (NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1-biphenyl-4,4'-diamine (TPD), and N,N',N'-tetranaphthyl-benzidine (TNB).

[0245] The n-type charge generation layer may be a pure n-type dopant layer, such as a layer of a positively charged 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, or an alkaline earth metal compound. In another embodiment, the metal may be one selected from Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, La, Ce, Sm, Eu, Tb, Dy, and Yb. More specifically, the n-type dopant may be selected from 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 layers or electron transport layers. The matrix material may be, for example, one selected from triazine compounds, hydroxyquinoline derivatives such as tris(8-hydroxyquinoline)aluminum, benzoxazole derivatives, and silafluorene derivatives.

[0246] In one embodiment, the p-type charge generation layer may comprise a compound of the following chemical formula X.

[0247] (X),

[0248] wherein each of A1 to A6 may be hydrogen, a halogen atom, nitrile (-CN), nitro (-NO2), sulfonyl (-SO2R), sulfoxide (-SOR), sulfonamide (-SO2NR), sulfonate (-SO3R), trifluoromethyl (-CF3), ester (-COOR), amide (-CONHR or -CONRR'), a substituted or unsubstituted straight-chain or branched C1-C 12 alkoxy, a substituted or unsubstituted straight-chain or branched C1-C 12 alkyl, a substituted or unsubstituted straight-chain or branched C2-C 12Alkenyl, substituted or unsubstituted aromatic or non-aromatic heterocycle, substituted or unsubstituted aryl, substituted or unsubstituted monoarylamine or diarylamine, substituted or unsubstituted aralkylamine, etc. In this text, each of the above R and R' may be substituted or unsubstituted C1-C 60 alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted 5- to 7-membered heterocycle, etc.

[0249] Examples of such p-type charge generation layers may be layers containing CNHAT:

[0250] (CNHAT).

[0251] The hole generation layer may be disposed on top of the n-type charge generation layer.

[0252] Regarding the method of manufacturing an organic electronic device, the alternative embodiments outlined above may be applied mutatis mutandis. For example, the charge generation layer may be manufactured to have an intermediate layer disposed between the n-type sublayer and the p-type sublayer.

[0253] According to one aspect, the OLED according to the present invention may include the following layer structure: a substrate is disposed adjacent to an anode electrode, the anode electrode is disposed adjacent to a first hole injection layer, the first hole injection layer is disposed adjacent to a first hole transport layer, the first hole transport layer is disposed adjacent to a first electron blocking layer, the first electron blocking layer is disposed adjacent to a first light emitting layer, the first light emitting layer is disposed adjacent to a first electron transport layer, the first electron transport layer is disposed adjacent to an n-type charge generation layer (n-type sublayer), the n-type charge generation layer is disposed adjacent to a hole generation layer (p-type sublayer), an intermediate layer may be disposed between the n-type sublayer and the p-type sublayer, the hole generation layer is disposed adjacent to a second hole transport layer, the second hole transport layer is disposed adjacent to a second electron blocking layer, the second electron blocking layer is disposed adjacent to a second light emitting layer, and an optional electron transport layer and / or an optional injection layer are disposed between the second light emitting layer and the cathode electrode.

[0254] Display device

[0255] According to another aspect, the present invention relates to a display device, the display device includes an organic electronic device according to the present invention, wherein the organic electronic device is an organic light emitting device.

[0256] Method for preparing an organic electronic device

[0257] According to another aspect, the present invention relates to a method for preparing an organic electronic device according to the present invention, wherein the method includes the step of depositing a compound of formula (I) according to the present invention on a solid support.

[0258] The deposition method may include:

[0259] - Deposition by vacuum thermal evaporation;

[0260] - Deposition by solution processing, preferably the processing is selected from spin coating, printing, casting; and / or

[0261] - Slot die coating.

[0262] Details and definitions of the present invention

[0263] Organic compounds as mentioned herein are generally any compounds containing carbon (except for some compounds that are usually referred to as inorganic compounds, such as carbonates, cyanides, carbon dioxide, diamond, etc.). The term organic compound as used herein also encompasses compounds such as organometallic compounds, for example, metallocene complexes, etc.

[0264] Unless otherwise explicitly mentioned, all compounds, groups, moieties, substituents, etc. shown herein, especially by structural formulas, by systematic names, etc., cover their corresponding partially deuterated and fully deuterated derivatives.

[0265] As used herein, the term "zero-valent" refers to a metal in the oxidation state 0, that is, specifically a metal from which no electrons have been removed. Zero-valent metals can exist in the form of zero-valent atoms, pure metals, alloys, etc.

[0266] As used herein, the term "trivalent" refers to a nitrogen atom having single bonds and double bonds and containing a lone pair of electrons.

[0267] As used herein, the term "hydrocarbyl group" should be understood to cover any organic group containing carbon atoms, especially organic groups such as alkyl, aryl, heteroaryl, heteroalkyl, especially groups that are commonly used as substituents in organic electronics.

[0268] As used herein, the term "conjugated system" refers to a system of alternating π-bonds and σ-bonds or a molecule having alternating single bonds and multiple bonds (i.e., double bonds), or a system having one or more diatomic structural units, in which the π-bonds between its atoms can be replaced by an atom with at least one lone electron pair, usually a divalent O or S atom.

[0269] As used herein, the term "alkyl" will cover straight-chain alkyls as well as branched-chain alkyls and cyclic alkyls. For example, C3 alkyl can be selected from n-propyl and isopropyl. Similarly, C4 alkyl covers n-butyl, sec-butyl, and tert-butyl. Similarly, C6 alkyl covers n-hexyl and cyclohexyl.

[0270] C n The subscript number n in refers to the total number of carbon atoms in the corresponding alkyl, arylene, heteroarylene, or aryl group.

[0271] As used herein, the term "aryl" or "arylene" will encompass phenyl (C6 aryl), fused aromatic substances such as naphthalene, anthracene, phenanthrene, tetracene, etc. It also encompasses biphenyl and lower or higher polyphenyls, such as terphenyl, phenyl-substituted biphenyl, phenyl-substituted terphenyl (such as a phenyl group with four phenyl groups), etc. "Arylene" or "heteroarylene" respectively refer to groups that are connected to two other moieties. In this specification, the term "aryl group" or "arylene group" may refer to a group containing at least one hydrocarbon aromatic moiety, and all elements of the hydrocarbon aromatic moiety may have p orbitals that form conjugation, such as a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyridyl group, a fluorenyl group, etc. Spiro compounds in which two aromatic moieties are connected to each other through a spiro atom are also encompassed, such as 9,9'-spirobi[9H-fluorene]yl. An aryl or arylene group may include monocyclic or fused polycyclic (i.e., connected by sharing adjacent pairs of carbon atoms) functional groups.

[0272] 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 moiety may have p orbitals that form conjugation. The heteroatom may be selected from N, O, S, B, Si, P, Se, preferably selected from N, O, and S. The heteroarylene ring may contain at least 1 to 3 heteroatoms. Preferably, the heteroarylene ring may contain at least 1 to 3 heteroatoms respectively selected from N, S, and / or O. Just as in the case of "aryl" / "arylene", the term "heteroaryl" encompasses, for example, spiro compounds in which two aromatic moieties are connected to each other, such as spiro[fluorene-9,9'-xanthene]. Other exemplary heteroaryl groups are diazine, triazine, dibenzofuran, dibenzothiophene, acridine, benzacridine, dibenzacridine, etc.

[0273] C n The subscript number n in -heteroaryl only refers to the number of carbon atoms and does not include the number of heteroatoms. In this case, it is obvious that a C3 heteroarylene group is an aromatic compound containing three carbon atoms, such as pyrazole, imidazole, oxazole, thiazole, etc.

[0274] The term "halogenated" refers to an organic compound in which one hydrogen atom is replaced by a halogen atom. The term "perhalogenated" refers to an organic compound in which all hydrogen atoms are replaced by halogen atoms. The meanings of the terms "fluorinated" and "perfluorinated" should be understood similarly.

[0275] As used herein, the term "alkenyl" refers to a group -CR 1 =CR 2 R 3 .

[0276] As used herein, the term "perhalogenated" refers to a hydrocarbyl group in which all hydrogen atoms of the hydrocarbyl group are replaced by halogen (F, Cl, Br, I) atoms.

[0277] As used herein, the term "alkoxy" refers to a structural moiety of the formula -OR, where R is a hydrocarbyl group, preferably an alkyl or cycloalkyl group.

[0278] As used herein, the term "thioalkyl" refers to a structural moiety of the formula -SR, where R is a hydrocarbyl group, preferably an alkyl or cycloalkyl group.

[0279] In this specification, the term single bond refers to a direct bond.

[0280] For the purposes of the present invention, if one of the hydrogen atoms contained in a group is replaced by another group, the group is "substituted" by the other group, where the other group is a substituent.

[0281] According to the present disclosure, in a formula showing the following bonding situations,

[0282]

[0283] Group A can be bonded to any suitable bonding position. In the case where the bond of A passes through more than one ring,

[0284]

[0285] Group A can be bonded to any suitable bonding position of each ring through which the bond passes.

[0286] For the purposes of the present invention, the expression "between" with respect to one layer between two other layers does not exclude the presence of other layers that may be disposed between one layer and one of the two other layers. For the purposes of the present invention, the expression "in direct contact" for two layers in direct contact with each other means that no other layer is disposed between the two layers. One layer deposited on top of another layer is considered to be in direct contact with this layer.

[0287] In the context of this specification, the term "substantially non-luminescent" or "non-luminescent" means that the contribution of a compound or layer to the visible emission spectrum of a device is less than 10%, preferably less than 5%, relative to the visible emission spectrum. The visible emission spectrum is an emission spectrum with a wavelength of about ≥380 nm to about ≤780 nm.

[0288] Regarding the organic light-emitting device of the present invention, the compounds mentioned in the experimental section can be most preferred.

[0289] An organic electroluminescent device (OLED) can be a bottom or top-emitting device.

[0290] On the other hand, it relates to a device comprising at least one organic electroluminescent device (OLED). A device comprising an organic light-emitting diode is, for example, a display or a lighting panel.

[0291] In the present invention, for the terms defined below, these definitions will apply unless different definitions are given in the claims or elsewhere in the present specification.

[0292] In the context of the present specification, the terms "different" or "different from" in relation to a matrix material mean that the matrix materials are different in terms of their structural formulas.

[0293] The energy levels of the highest occupied molecular orbital (also referred to as HOMO) and the lowest unoccupied molecular orbital (also referred to as LUMO) are measured in electron volts (eV).

[0294] The terms "OLED" and "organic light-emitting diode" are used interchangeably and have the same meaning. As used herein, the term "organic electroluminescent device" may include an organic light-emitting diode and an organic light-emitting transistor (OLET).

[0295] As used herein, "weight percentage", "wt.%", "wt%", "percentage by weight", "weight %" and their variants refer to expressing a composition, component, substance or reagent as the weight of the component, substance or reagent in the corresponding electron transport layer divided by the total weight of its corresponding electron transport layer and multiplied by 100. It should be understood that the total weight percentage amounts of all components, substances and reagents of the corresponding electron transport layer and electron injection layer are selected such that they do not exceed 100 weight %.

[0296] As used herein, "volume percentage", "vol.%", "percentage by volume", "volume %" and their variants refer to expressing a composition, component, substance or reagent as the volume of the component, substance or reagent in the corresponding electron transport layer divided by the total volume of its corresponding electron transport layer and multiplied by 100. It should be understood that the total volume percentage amounts of all components, substances and reagents of the cathode layer are selected such that they do not exceed 100 volume %.

[0297] 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 a quantifiable variation that can occur. Whether or not modified by the term "about", the claims include equivalents of the quantity.

[0298] It should be noted that unless the context clearly indicates otherwise, the singular forms "a", "an" and "the" as used in this specification and the appended claims include plural referents.

[0299] The terms "free of", "does not contain", "does not comprise" do not exclude impurities. The impurities have no technical influence on the object to be achieved by the present invention. The term "free of" a compound means that such compound / material is not intentionally added to the layer during processing.

[0300] Preferably, the semiconductor layer comprising the compound of formula (I) is substantially non-luminescent or non-luminescent.

[0301] The operating voltage, also designated as U, is measured in volts (V) at 10 milliamperes per square centimeter (mA / cm 2 2).

[0302] The candela per ampere efficiency, also designated as cd / A efficiency, is measured in candela per ampere at 10 milliamperes per square centimeter (mA / cm2).

[0303] The external quantum efficiency, also designated as EQE, is measured in percent (%).

[0304] The color space is described by the coordinates CIE-x and CIE-y (International Commission on Illumination 1931). For blue emission, CIE-y is of particular importance. The smaller CIE-y, the deeper the blue. Compare the efficiency values at the same CIE-y.

[0305] The highest occupied molecular orbital (also designated as HOMO) and the lowest unoccupied molecular orbital (also designated as LUMO) are measured in electron volts (eV).

[0306] The terms "OLED", "organic light-emitting diode", "organic light-emitting device", "organic optoelectronic device" and "organic light-emitting diode" are used interchangeably and have the same meaning.

[0307] The terms "service life" and "lifetime" are used interchangeably and have the same meaning.

[0308] The anode and the cathode may be described as anode electrode / cathode electrode or anode electrode / cathode electrode or anode electrode layer / cathode electrode layer.

[0309] Room temperature, also designated as ambient temperature, is 23 °C.

[0310] In the following, the embodiments are illustrated in more detail with reference to the examples. However, the present disclosure is not limited to the following examples. Now, the exemplary aspects will be described in detail. BRIEF DESCRIPTION OF THE DRAWINGS

[0311] The above-described components in the described embodiments, as well as the claimed components and the components used according to the present invention, do not have any special exceptions in terms of their size, shape, material selection and technical principle, and thus the known selection criteria in the relevant fields can be applied without limitation.

[0312] Other details, features, and advantages of the objects of the present invention are disclosed in the dependent claims and the following description of the corresponding drawings, which illustrate, by way of example, preferred embodiments according to the present invention. However, any embodiment may not necessarily represent the entire scope of the present invention, and thus the scope of the present invention is interpreted with reference to the claims and the present text. It should be understood that the above general description and the following detailed description are merely exemplary and explanatory, and are intended to further exemplify the claimed invention.

[0313] Figure 1 is a schematic cross-sectional view of an organic semiconductor device according to an exemplary embodiment of the present invention;

[0314] Figure 2 is a schematic cross-sectional view of an organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention;

[0315] Figure 3 is a schematic cross-sectional view of an OLED according to an exemplary embodiment of the present invention.

[0316] 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. Detailed Embodiments

[0317] Hereinafter, the accompanying drawings are exemplified in more detail with reference to the embodiments. However, the present disclosure is not limited by the following drawings.

[0318] In this document, when a first element is said to be formed or disposed "on" or "above" a second element, the first element may be directly disposed on the second element, or one or more other elements may be disposed therebetween. When a first element is said to be formed or disposed "directly on" or "directly above" a second element, no other element is disposed therebetween.

[0319] Figure 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 light-emitting layer (EML) 125, and a semiconductor layer 160 including or consisting of a semiconductor material according to the present invention. The semiconductor layer 160 including or consisting of a semiconductor material according to the present invention is formed on the EML 125. A cathode 190 is disposed above the organic semiconductor layer 160.

[0320] Figure 2FIG. 0 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. In this embodiment, the electron transport layer is a semiconductor layer according to the present invention. An electron transport layer (ETL) 160 is formed on the EML 150. An electron injection layer (EIL) 180 is disposed on the electron transport layer (ETL) 160. A cathode 190 is disposed directly on the electron injection layer (EIL) 180.

[0321] Figure 3 FIG. 4 is a schematic cross-sectional view of the OLED 100 according to another exemplary embodiment of the present invention. Figure 3 Differing from Figure 2 is that Figure 3 the OLED 100 of

[0322] Referring to Figure 3 FIG. 15, 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.

[0323] In Figure 3 this embodiment of

[0324] Figure 4 FIG. 24 is a schematic cross-sectional view of the OLED 100 according to another exemplary embodiment of the present invention. Figure 4 Differing from Figure 3 is that Figure 4 the OLED 100 of

[0325] Referring to 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 emission 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 emission 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.

[0326] In Figure 4 this embodiment, the HBL 155 is a semiconductor layer including a compound of formula (I).

[0327] Although not shown in Figure 1 , Figure 2 , Figure 3 and Figure 4 , a sealing layer may be additionally formed on the cathode electrode 190 to seal the OLED 100. In addition, various other modifications can be made thereto.

[0328] Hereinafter, the embodiments will be illustrated in more detail with reference to the examples. However, the present disclosure is not limited to the following examples.

[0329] Synthesis procedure

[0330] 4-Phenyl-2-(2'-(3,5,6-triphenylpyrazin-2-yl)-[1,1'-biphenyl]-3-yl)quinazoline (E1)

[0331]

[0332] The 3-neck round-bottom flask was flushed with nitrogen and charged with 2-(2-bromophenyl)-3,5,6-triphenylpyrazine (CAS 2368824-18-2, 1 equiv, 11.9 g), 4-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)quinazoline (CAS 1852465-26-9, 0.95 equiv, 12.8 g), chloro(crotyl)(2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl)palladium(II) (CAS 1798781-99-3, 0.01 equiv, 0.2 g), and potassium phosphate (CAS 7778-53-2, 2 equiv, 12.4 g). A degassed mixture of 120 mL of dioxane and 30 mL of water was added. The reaction mixture was stirred overnight at 50 °C under a nitrogen atmosphere. The reaction mixture was then cooled and the solvent was evaporated. The crude product was extracted in 250 mL of chloroform and washed with water. The combined organic phases were dried and filtered through a silica pad. The solvent was partially evaporated under reduced pressure and hexane was added. The white solid precipitate was filtered off. Final purification was carried out by sublimation to give the product as a white crystalline solid. Yield: 11.5 g (67%); ESI-MS: 665

[0333] 4-Phenyl-2-(3'-(3,5,6-triphenylpyrazin-2-yl)-[1,1'-biphenyl]-3-yl)quinazoline (E2)

[0334]

[0335] The 3-neck round-bottom flask was flushed with nitrogen and charged with 2-(3-chlorophenyl)-4-phenylquinazoline (CAS 540466-41-9, 1 equivalent, 25.0 g), 2,3,5-triphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrazine (CAS 2396743-64-7, 1.1 equivalents, 44.3 g), chloro(crotyl)(2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl)palladium(II) (CAS 1798781-99-3, 0.01 equivalent, 0.5 g), and potassium phosphate (CAS 7778-53-2, 2 equivalents, 33.5 g). A degassed mixture of 440 mL of dioxane and 80 mL of water was added. The reaction mixture was stirred overnight at 45 °C under a nitrogen atmosphere. After cooling to room temperature, a brown suspension formed. The starting solid material was filtered off and washed with dioxane and water. The product was then dissolved in 1.1 L of toluene at an elevated temperature and filtered hot through a silica pad. The first portion of the filtrate was discarded and the pad was additionally eluted with an excess of dichloromethane. The solvent was then evaporated and the crude product was refluxed in 300 mL of methyl tert-butyl ether and filtered. Final purification was carried out by sublimation to give the product as a white powder. Yield: 26.4 g (52%); ESI-MS: 665

[0336] 4,6-Diphenyl-2-(3'-(3,5,6-triphenylpyrazin-2-yl)-[1,1'-biphenyl]-3-yl)pyrimidine (E3)

[0337]

[0338] The 3-neck round-bottom flask was flushed with nitrogen and charged with 1 equivalent (18.9 g) of 2-(3-bromophenyl)-3,5,6-triphenylpyrazine (CAS 2368824-17-1), 1 equivalent (20.1 g) of 4,6-diphenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (CAS 1381862-91-4), 0.2 equivalent (1.0 g) of tetrakis(triphenylphosphine)palladium(0) (CAS 14221-01-3), and 3 equivalents (18.0 g) of potassium carbonate (CAS 584-08-7). A degassed mixture of 260 mL of dioxane and 65 mL of water was added. The reaction mixture was stirred overnight at 70 °C under a nitrogen atmosphere. After cooling to room temperature, a dark gray suspension was formed. The starting solid material was filtered off and washed with dioxane, water, and methanol. The product was then extracted with toluene in a Soxhlet extractor. After cooling the extract, a white precipitate formed, which was then filtered and washed with hexane. The product was then washed in 300 mL of hot toluene. Final purification was carried out by sublimation to give the product as a white powder. Yield: 23.9 g (79%); ESI-MS: 691

[0339] 4,6-Diphenyl-2-(4'-(3,5,6-triphenylpyrazin-2-yl)-[1,1'-biphenyl]-3-yl)pyrimidine (E4)

[0340]

[0341] The 3-neck round-bottom flask was flushed with nitrogen and charged with 1 equivalent (18.9 g) of 2-(4-bromophenyl)-3,5,6-triphenylpyrazine (CAS 943442-81-7), 1 equivalent (20.1 g) of 4,6-diphenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (CAS 1381862-91-4), 0.02 equivalent (1.0 g) of tetrakis(triphenylphosphine)palladium(0) (CAS 14221-01-3), and 3 equivalents (18.0 g) of potassium carbonate (CAS 584-08-7). A degassed mixture of 260 mL of dioxane and 65 mL of water was added. The reaction mixture was stirred overnight at 70 °C under a nitrogen atmosphere. After cooling to room temperature, a gray suspension was formed. The starting solid material was filtered off and washed with dioxane and water. The product was then extracted with toluene in a Soxhlet extractor. After cooling the extract, a white precipitate formed. The solid was filtered off and washed with hexane. Final purification was carried out by sublimation to give the product as a white powder. Yield: 23.9 g (79%); ESI-MS: 691

[0342] 4,6-Diphenyl-2-(3'-(3,5,6-triphenylpyrazin-2-yl)-[1,1'-biphenyl]-4-yl)pyrimidine (E5)

[0343]

[0344] A 3-neck round-bottom flask was flushed with nitrogen and charged with 4,6-diphenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (CAS 1613163-88-4, 1 equiv, 25.0 g), 2-(3-bromophenyl)-3,5,6-triphenylpyrazine (CAS 2368824-17-1, 1 equiv, 23.4 g), tetrakis(triphenylphosphine)palladium(0) (CAS 14221-01-3, 0.02 equiv, 1.3 g), and potassium carbonate (CAS 584-08-7, 2 equiv, 14.9 g). A degassed mixture of 480 mL of THF and 60 mL of water was added. The reaction mixture was stirred overnight at 75 °C under a nitrogen atmosphere. After cooling to room temperature, a yellow suspension formed. The starting solid material was filtered off and washed with THF and water. The product was then dissolved in 800 mL of chloroform and filtered through a silica pad. The resulting solution was partially evaporated and a hexane mixture containing 5% methanol was added. A white precipitate formed and the solid was filtered off. Final purification was carried out by sublimation to give the product as a white powder. Yield: 18.9 g (51%), ESI-MS: 691

[0345] 4-Phenyl-2-(3'-(3,5,6-triphenylpyrazin-2-yl)-[1,1'-biphenyl]-3-yl)benzo[h]quinazoline (E6)

[0346]

[0347] The 3-neck round-bottom flask was flushed with nitrogen and charged with 4-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzo[h]quinazoline (CAS 2639481-16-4, 1 equiv, 20.0 g), 2-(3-bromophenyl)-3,5,6-triphenylpyrazine (CAS 2368824-17-1, 1 equiv, 20.2 g), tetrakis(triphenylphosphine)palladium(0) (CAS 14221-01-3, 0.02 equiv, 1.0 g), and potassium carbonate (CAS 584-08-7, 3 equiv, 12.1 g). A degassed mixture of 200 mL of dioxane and 50 mL of water was added. The reaction mixture was stirred overnight at 75 °C under a nitrogen atmosphere. After cooling to room temperature, a dark gray suspension was formed. The starting solid material was filtered off and washed with dioxane, water, and methanol. The product was then extracted with chlorobenzene in a Soxhlet extractor. After cooling the extract, a white precipitate formed, which was filtered and washed with hexane. The solid was washed in 400 mL of hot THF and filtered. The product was recrystallized from chlorobenzene. Final purification was carried out by sublimation to give the product as a white powder. Yield: 18.4 g (59%). ESI-MS: 715

[0348] 4-Phenyl-2-(3'-(3,5,6-triphenylpyrazin-2-yl)-[1,1'-biphenyl]-2-yl)quinazoline (E7)

[0349]

[0350] The 3-neck round-bottom flask was flushed with nitrogen and charged with 2-(2-chlorophenyl)-4-phenylquinazoline (CAS 1283751-33-6, 1 equiv, 12.8 g), 2,3,5-triphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrazine (CAS 2396743-64-7, 1.05 equiv, 21.7 g), chloro(crotyl)(2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl)palladium(II) (CAS 1798781-99-3, 0.03 equiv, 7.3 g), and potassium phosphate (CAS 7778-53-2, 2 equiv, 17.2 g). A degassed mixture of 300 mL of dioxane and 100 mL of water was added. The reaction mixture was stirred overnight at 90 °C under a nitrogen atmosphere. After cooling to room temperature, a gray suspension was formed. The starting solid material was filtered off and washed with dioxane, water, and methanol. The product was then dissolved in dichloromethane and filtered through a silica pad. The resulting solution was partially evaporated and methanol was added. A white precipitate formed and was filtered. Final purification was carried out by sublimation to give the product as a white powder. Yield: 15.4 g (57%). ESI-MS: 665

[0351] Supporting materials for device experiments

[0352] F1 is

[0353] CAS 1607480-22-7.

[0354] F2 is

[0355] CAS 1464822-27-2.

[0356] F3 is

[0357] CAS 2244287-14-5.

[0358] F4 is

[0359] CAS 1242056-42-3.

[0360] PD2 is

[0361] CAS 1224447-88-4.

[0362] LiQ is lithium 8-hydroxyquinoline, CAS 850918-68-2.

[0363] BH1 is

[0364] CAS 2457172-82-4.

[0365] BD1 is

[0366] CAS 2482607-57-6.

[0367] ITO is indium tin oxide.

[0368] Comparative compound

[0369] C1 C2

[0370] C3 C4

[0371] OLED device

[0372] Blue fluorescent top-emitting OLED

[0373] Table 1a schematically describes the model device used for the OLED test.

[0374] Table 1:

[0375]

[0376] The results are given in Tables 2 to 5.

[0377] Table 2

[0378]

[0379] Compared with compound C1 representing the state of the art, the compounds of the present invention can achieve a longer lifetime and a higher current efficiency.

[0380] Table 3

[0381]

[0382] Compared with compound C2 representing the state of the art, the compounds of the present invention can achieve a longer lifetime and a higher current efficiency.

[0383] Table 4

[0384]

[0385] Compared with compound C3 representing the state of the art, the compounds of the present invention can achieve a longer lifetime and a higher current efficiency.

[0386] Table 5

[0387]

[0388] Compared with compound C4 representing the state of the art, compound E6 of the present invention can achieve a longer lifetime and a higher current efficiency.

[0389] The technical features disclosed in the above description and the dependent claims can be used, both individually and in any combination thereof, as materials for implementing the aspects disclosed in the independent claims in different forms.

Claims

1. A compound of formula (I), (I) wherein - A, A', and A" are independently selected from substituted or unsubstituted C1 to C 20 alkyl, substituted or unsubstituted C1 to C 20 alkenyl, substituted or unsubstituted C6 to C 60 aryl, and substituted or unsubstituted C2 to C 60 heteroaryl; - L and L" are independently selected from substituted or unsubstituted C6 to C 60 aryl and substituted or unsubstituted C2 to C 60 heteroaryl, and L' is selected from H, D, C1 to C 20 alkyl, substituted or unsubstituted C1 to C 20 alkenyl, substituted or unsubstituted C6 to C 60 aryl and substituted or unsubstituted C2 to C 60 heteroaryl; or - L is selected from substituted or unsubstituted C6 to C 60 aryl and substituted and unsubstituted C2 to C 60 heteroaryl, and L' and L" together form a fused 6-membered aromatic ring, wherein the fused 6 - membered aromatic ring - is unsubstituted, or - substituted by one or more substituents independently selected from C6 to C 56 aryl, provided that the total number of C atoms in all substituents does not exceed 56, or - Condensed with a second 6-membered aromatic ring, where the condensed 6-membered aromatic ring and the second 6-membered aromatic ring are unsubstituted, or at least one of the condensed 6-membered aromatic ring and the second 6-membered aromatic ring is substituted by one or more substituents independently selected from C6 to C 40 aryl, provided that the total number of C atoms in all substituents does not exceed 40; - E is independently selected from H, D, D, halogen, SiR a R b R c (wherein R a , R b and R c are independently selected from C1-C6 alkyl and phenyl), C1-C6 alkyl, C1-C6 alkoxy, CN and P(=O)R d R e (wherein R d and R e are independently selected from C1-C6 alkyl and phenyl); - G is independently selected from H, D, halogen, SiR a R b R c (wherein R a , R b and R c are independently selected from C1-C6 alkyl and phenyl), C1-C6 alkyl, C1-C6 alkoxy, CN and P(=O)R d R e (wherein R d and R e are independently selected from C1-C6 alkyl and phenyl).

2. The compound according to claim 1, wherein A, A' and A" are independently selected from C6 to C 60 aryl.

3. The compound according to claim 1 or 2, wherein A, A' and A" are each phenyl.

4. A compound according to any one of the preceding claims, wherein L and L" are independently selected from substituted or unsubstituted C6 to C 60 aryl, and L' is H; or - L is selected from substituted or unsubstituted C6 to C 60 aryl, and L' and L" together form a fused 6-membered aromatic ring, wherein the fused 6 - membered aromatic ring - is unsubstituted, or - is fused to a second 6 - membered aromatic ring, wherein the fused 6 - membered aromatic ring and the second 6 - membered aromatic ring are unsubstituted.

5. The compound according to any one of the preceding claims, wherein L and L" are each phenyl, and L' is H; or - L is phenyl, and L' and L" together form an unsubstituted fused 6 - membered aromatic ring.

6. The compound according to any one of the preceding claims, wherein E is H.

7. The compound according to any one of the preceding claims, wherein G is H.

8. A semiconductor material, the semiconductor material comprising a compound of formula (I) according to any one of the preceding claims.

9. An organic electronic device, the organic electronic device comprising a semiconductor layer, wherein the semiconductor layer comprises the semiconductor material according to claim 8.

10. The organic electronic device according to claim 9, wherein the semiconductor layer is a hole - blocking layer and / or an electron - transporting layer and / or an electron - injecting layer.

11. The organic electronic device according to claim 9 or 10, wherein the semiconductor layer is a hole - blocking layer.

12. The organic electronic device according to claim 11, wherein the organic electronic device further comprises a light - emitting layer and an electron - transporting layer, and the hole - blocking layer is disposed between the light - emitting layer and the electron - transporting layer.

13. The organic electronic device according to claim 12, wherein the organic electronic device is an organic light - emitting diode.

14. A display device, the display device comprising the organic electronic device according to claim 13.

15. A method for preparing the organic electronic device according to claim 12 or 13, wherein the method comprises the step of depositing a compound according to any one of claims 1 to 8 on a solid support.

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